#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:33:38 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178875 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/04/4110430.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_4110430
loop_
_publ_author_name
'Josephine S. Nakhla'
'Jeff W. Kampf'
'John P. Wolfe'
_publ_section_title
;
 Intramolecular Pd-Catalyzed Carboetherification and Carboamination.
 Influence of Catalyst Structure on Reaction Mechanism and Product
 Stereochemistry
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2893
_journal_page_last               2901
_journal_paper_doi               10.1021/ja057489m
_journal_volume                  128
_journal_year                    2006
_chemical_formula_moiety         'C31 H29 N'
_chemical_formula_sum            'C31 H29 N'
_chemical_formula_weight         415.55
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.298(4)
_cell_angle_beta                 90.865(4)
_cell_angle_gamma                112.971(4)
_cell_formula_units_Z            2
_cell_length_a                   10.268(3)
_cell_length_b                   10.634(3)
_cell_length_c                   12.104(3)
_cell_measurement_reflns_used    7294
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      23.33
_cell_measurement_theta_min      2.23
_cell_volume                     1132.6(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29499
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.9727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  Blessing, R. Acta Cryst. (1995) A51 33-38.
  Sheldrick, G.  SADABS (Version 2.10) Bruker/Siemens area
  detector absorption and other corrections, University of
  Gottingen, Germany 2003.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0417
_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)+(0.0535P)²+0.3193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                4671
_reflns_number_total             5634
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja057489msi20051102_021032.cif
_cod_data_source_block           jn160
_cod_original_cell_volume        1132.6(6)
_cod_database_code               4110430
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.07021(9) 0.25593(10) 0.37268(8) 0.02520(19) Uani 1 1 d .
C1 C 0.15491(11) 0.36975(12) 0.48633(9) 0.0240(2) Uani 1 1 d .
H1A H 0.1226 0.4508 0.5062 0.029 Uiso 1 1 calc R
C2 C 0.30754(11) 0.42666(13) 0.45691(10) 0.0281(2) Uani 1 1 d .
H2A H 0.3278 0.5128 0.4341 0.034 Uiso 1 1 calc R
H2B H 0.3798 0.4549 0.5260 0.034 Uiso 1 1 calc R
C3 C 0.30974(12) 0.29827(13) 0.35304(10) 0.0284(2) Uani 1 1 d .
H3A H 0.3296 0.2292 0.3814 0.034 Uiso 1 1 calc R
H3B H 0.3830 0.3333 0.3050 0.034 Uiso 1 1 calc R
C4 C 0.15742(11) 0.22544(12) 0.28103(9) 0.0240(2) Uani 1 1 d .
H4A H 0.1271 0.1171 0.2436 0.029 Uiso 1 1 calc R
C5 C 0.14008(11) 0.31363(12) 0.59095(9) 0.0254(2) Uani 1 1 d .
H5A H 0.0397 0.2873 0.6076 0.031 Uiso 1 1 calc R
C6 C 0.17787(13) 0.18185(13) 0.57480(11) 0.0330(3) Uani 1 1 d .
H6A H 0.1091 0.1126 0.6067 0.040 Uiso 1 1 calc R
H6B H 0.1744 0.1289 0.4897 0.040 Uiso 1 1 calc R
C7 C 0.33111(14) 0.24595(14) 0.64383(11) 0.0357(3) Uani 1 1 d .
H7A H 0.3401 0.1820 0.6844 0.043 Uiso 1 1 calc R
H7B H 0.4031 0.2582 0.5902 0.043 Uiso 1 1 calc R
C8 C 0.34936(12) 0.39248(13) 0.73241(10) 0.0287(2) Uani 1 1 d .
C9 C 0.45501(12) 0.48760(15) 0.83167(11) 0.0356(3) Uani 1 1 d .
H9A H 0.5274 0.4615 0.8534 0.043 Uiso 1 1 calc R
C10 C 0.45310(13) 0.62068(15) 0.89829(11) 0.0384(3) Uani 1 1 d .
H10A H 0.5235 0.6850 0.9670 0.046 Uiso 1 1 calc R
C11 C 0.34944(14) 0.66102(14) 0.86577(11) 0.0362(3) Uani 1 1 d .
H11A H 0.3511 0.7538 0.9111 0.043 Uiso 1 1 calc R
C12 C 0.24291(12) 0.56640(13) 0.76713(10) 0.0296(2) Uani 1 1 d .
H12A H 0.1718 0.5938 0.7449 0.036 Uiso 1 1 calc R
C13 C 0.24243(11) 0.43136(12) 0.70180(9) 0.0252(2) Uani 1 1 d .
C14 C 0.14964(11) 0.28681(12) 0.18524(9) 0.0235(2) Uani 1 1 d .
C15 C 0.12900(12) 0.41423(13) 0.20825(10) 0.0296(2) Uani 1 1 d .
H15A H 0.1124 0.4619 0.2846 0.036 Uiso 1 1 calc R
C16 C 0.13242(14) 0.47249(14) 0.12019(12) 0.0353(3) Uani 1 1 d .
H16A H 0.1187 0.5598 0.1369 0.042 Uiso 1 1 calc R
C17 C 0.15572(12) 0.40358(14) 0.00843(11) 0.0336(3) Uani 1 1 d .
H17A H 0.1590 0.4439 -0.0513 0.040 Uiso 1 1 calc R
C18 C 0.17429(12) 0.27559(14) -0.01585(10) 0.0314(2) Uani 1 1 d .
H18A H 0.1896 0.2276 -0.0926 0.038 Uiso 1 1 calc R
C19 C 0.17056(12) 0.21721(13) 0.07172(10) 0.0271(2) Uani 1 1 d .
H19A H 0.1824 0.1288 0.0540 0.033 Uiso 1 1 calc R
C20 C -0.07736(11) 0.19963(11) 0.34535(9) 0.0230(2) Uani 1 1 d .
C21 C -0.15131(11) 0.09431(12) 0.23230(9) 0.0254(2) Uani 1 1 d .
H21A H -0.0985 0.0642 0.1733 0.030 Uiso 1 1 calc R
C22 C -0.29960(11) 0.03418(12) 0.20606(9) 0.0257(2) Uani 1 1 d .
H22A H -0.3460 -0.0362 0.1291 0.031 Uiso 1 1 calc R
C23 C -0.38339(11) 0.07376(12) 0.28938(9) 0.0240(2) Uani 1 1 d .
C24 C -0.30974(11) 0.18117(12) 0.40007(9) 0.0246(2) Uani 1 1 d .
H24A H -0.3631 0.2123 0.4581 0.030 Uiso 1 1 calc R
C25 C -0.16114(11) 0.24377(12) 0.42793(9) 0.0238(2) Uani 1 1 d .
H25A H -0.1152 0.3175 0.5038 0.029 Uiso 1 1 calc R
C26 C -0.54231(11) 0.00174(12) 0.26330(10) 0.0246(2) Uani 1 1 d .
C27 C -0.61855(12) -0.04042(13) 0.15054(10) 0.0288(2) Uani 1 1 d .
H27A H -0.5677 -0.0196 0.0892 0.035 Uiso 1 1 calc R
C28 C -0.76739(12) -0.11214(13) 0.12702(11) 0.0311(2) Uani 1 1 d .
H28A H -0.8171 -0.1408 0.0498 0.037 Uiso 1 1 calc R
C29 C -0.84374(12) -0.14205(12) 0.21565(11) 0.0303(2) Uani 1 1 d .
H29A H -0.9455 -0.1912 0.1995 0.036 Uiso 1 1 calc R
C30 C -0.77021(12) -0.09956(13) 0.32821(11) 0.0309(2) Uani 1 1 d .
H30A H -0.8217 -0.1187 0.3896 0.037 Uiso 1 1 calc R
C31 C -0.62143(12) -0.02912(13) 0.35119(10) 0.0291(2) Uani 1 1 d .
H31A H -0.5724 -0.0013 0.4285 0.035 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C20 N1 C1 124.12(9)
C20 N1 C4 121.30(9)
C1 N1 C4 113.67(8)
N1 C1 C2 102.77(8)
N1 C1 C5 113.58(9)
C2 C1 C5 114.81(8)
C3 C2 C1 104.97(9)
C2 C3 C4 103.43(9)
N1 C4 C14 113.60(9)
N1 C4 C3 102.81(9)
C14 C4 C3 111.72(9)
C13 C5 C6 102.97(9)
C13 C5 C1 110.77(9)
C6 C5 C1 116.56(9)
C7 C6 C5 106.52(10)
C8 C7 C6 103.57(9)
C9 C8 C13 119.95(11)
C9 C8 C7 129.43(11)
C13 C8 C7 110.59(10)
C10 C9 C8 119.21(11)
C9 C10 C11 120.77(11)
C10 C11 C12 120.46(12)
C13 C12 C11 118.92(11)
C12 C13 C8 120.64(10)
C12 C13 C5 128.02(10)
C8 C13 C5 111.27(10)
C15 C14 C19 118.59(10)
C15 C14 C4 122.28(10)
C19 C14 C4 119.07(10)
C14 C15 C16 120.52(11)
C17 C16 C15 120.26(11)
C18 C17 C16 119.65(10)
C17 C18 C19 120.15(11)
C18 C19 C14 120.81(11)
N1 C20 C25 122.10(10)
N1 C20 C21 121.01(9)
C25 C20 C21 116.89(9)
C22 C21 C20 121.07(10)
C21 C22 C23 122.14(10)
C24 C23 C22 116.67(10)
C24 C23 C26 121.51(10)
C22 C23 C26 121.79(10)
C25 C24 C23 122.13(10)
C24 C25 C20 121.04(10)
C31 C26 C27 117.57(10)
C31 C26 C23 120.39(10)
C27 C26 C23 122.03(10)
C28 C27 C26 121.05(11)
C29 C28 C27 120.36(11)
C28 C29 C30 119.40(10)
C29 C30 C31 120.13(11)
C30 C31 C26 121.48(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C20 1.3820(14)
N1 C1 1.4682(14)
N1 C4 1.4685(13)
C1 C2 1.5390(15)
C1 C5 1.5548(14)
C2 C3 1.5283(17)
C3 C4 1.5405(15)
C4 C14 1.5213(14)
C5 C13 1.5141(15)
C5 C6 1.5486(16)
C6 C7 1.5445(18)
C7 C8 1.5082(18)
C8 C9 1.3944(17)
C8 C13 1.3990(15)
C9 C10 1.386(2)
C10 C11 1.3882(19)
C11 C12 1.3936(17)
C12 C13 1.3897(17)
C14 C15 1.3911(16)
C14 C19 1.3938(15)
C15 C16 1.3935(16)
C16 C17 1.3841(19)
C17 C18 1.3838(18)
C18 C19 1.3886(16)
C20 C25 1.4109(15)
C20 C21 1.4125(15)
C21 C22 1.3855(15)
C22 C23 1.4010(15)
C23 C24 1.3984(15)
C23 C26 1.4827(15)
C24 C25 1.3887(15)
C26 C31 1.3958(16)
C26 C27 1.4023(15)
C27 C28 1.3900(16)
C28 C29 1.3867(18)
C29 C30 1.3880(17)
C30 C31 1.3887(16)
