#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:33:38 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178875 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/04/4110428.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_4110428
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         'C25 H25 N'
_chemical_formula_sum            'C25 H25 N'
_chemical_formula_weight         339.46
_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                 92.893(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.526(2)
_cell_length_b                   7.0230(15)
_cell_length_c                   24.427(5)
_cell_measurement_reflns_used    3185
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      3.01
_cell_volume                     1803.4(6)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0587
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15776
_diffrn_reflns_theta_full        26.52
_diffrn_reflns_theta_max         26.52
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0441
_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)+(0.0453P)²+0.7948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                2483
_reflns_number_total             3694
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja057489msi20051102_020802.cif
_cod_data_source_block           jnc
_cod_original_cell_volume        1803.5(7)
_cod_database_code               4110428
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 0.94367(13) 0.6516(2) 0.88566(6) 0.0279(4) Uani 1 1 d .
C1 C 1.07926(16) 0.6359(3) 0.87640(8) 0.0287(4) Uani 1 1 d .
H1A H 1.0973 0.5175 0.8562 0.034 Uiso 1 1 calc R
H1B H 1.1300 0.6357 0.9116 0.034 Uiso 1 1 calc R
C2 C 1.10994(17) 0.8105(3) 0.84252(8) 0.0295(4) Uani 1 1 d .
H2A H 1.1103 0.7783 0.8031 0.035 Uiso 1 1 calc R
H2B H 1.1940 0.8638 0.8544 0.035 Uiso 1 1 calc R
C3 C 1.00371(17) 0.9513(3) 0.85341(8) 0.0290(4) Uani 1 1 d .
H3A H 0.9860 1.0341 0.8211 0.035 Uiso 1 1 calc R
H3B H 1.0275 1.0325 0.8854 0.035 Uiso 1 1 calc R
C4 C 0.88713(16) 0.8292(3) 0.86474(7) 0.0256(4) Uani 1 1 d .
H4A H 0.8402 0.8907 0.8946 0.031 Uiso 1 1 calc R
C5 C 0.79387(17) 0.7979(3) 0.81495(7) 0.0257(4) Uani 1 1 d .
H5A H 0.7252 0.7118 0.8272 0.031 Uiso 1 1 calc R
C6 C 0.84609(18) 0.7074(3) 0.76293(8) 0.0318(4) Uani 1 1 d .
H6A H 0.9303 0.7611 0.7553 0.038 Uiso 1 1 calc R
H6B H 0.8539 0.5676 0.7669 0.038 Uiso 1 1 calc R
C7 C 0.74603(19) 0.7596(3) 0.71712(8) 0.0324(5) Uani 1 1 d .
H7A H 0.7848 0.7683 0.6811 0.039 Uiso 1 1 calc R
H7B H 0.6760 0.6654 0.7148 0.039 Uiso 1 1 calc R
C8 C 0.69968(16) 0.9508(3) 0.73537(8) 0.0271(4) Uani 1 1 d .
C9 C 0.63391(17) 1.0912(3) 0.70545(8) 0.0316(5) Uani 1 1 d .
H9A H 0.6129 1.0747 0.6675 0.038 Uiso 1 1 calc R
C10 C 0.59964(17) 1.2562(3) 0.73237(8) 0.0332(5) Uani 1 1 d .
H10A H 0.5537 1.3529 0.7127 0.040 Uiso 1 1 calc R
C11 C 0.63173(17) 1.2815(3) 0.78784(9) 0.0323(5) Uani 1 1 d .
H11A H 0.6087 1.3965 0.8053 0.039 Uiso 1 1 calc R
C12 C 0.69702(16) 1.1416(3) 0.81830(8) 0.0276(4) Uani 1 1 d .
H12A H 0.7189 1.1594 0.8562 0.033 Uiso 1 1 calc R
C13 C 0.72916(16) 0.9747(2) 0.79142(7) 0.0238(4) Uani 1 1 d .
C14 C 0.88229(16) 0.5242(2) 0.91766(7) 0.0240(4) Uani 1 1 d .
C15 C 0.75341(17) 0.5443(3) 0.92928(7) 0.0268(4) Uani 1 1 d .
H15A H 0.7063 0.6494 0.9145 0.032 Uiso 1 1 calc R
C16 C 0.69415(17) 0.4136(3) 0.96185(7) 0.0257(4) Uani 1 1 d .
H16A H 0.6069 0.4316 0.9687 0.031 Uiso 1 1 calc R
C17 C 0.75782(16) 0.2560(2) 0.98505(7) 0.0236(4) Uani 1 1 d .
C18 C 0.88581(17) 0.2383(3) 0.97342(8) 0.0278(4) Uani 1 1 d .
H18A H 0.9329 0.1338 0.9885 0.033 Uiso 1 1 calc R
C19 C 0.94644(17) 0.3661(3) 0.94096(7) 0.0273(4) Uani 1 1 d .
H19A H 1.0336 0.3471 0.9342 0.033 Uiso 1 1 calc R
C20 C 0.69423(16) 0.1200(3) 1.02091(7) 0.0238(4) Uani 1 1 d .
C21 C 0.59257(17) 0.1742(3) 1.05185(7) 0.0283(4) Uani 1 1 d .
H21A H 0.5626 0.3017 1.0495 0.034 Uiso 1 1 calc R
C22 C 0.53406(17) 0.0471(3) 1.08591(8) 0.0308(4) Uani 1 1 d .
H22A H 0.4644 0.0878 1.1063 0.037 Uiso 1 1 calc R
C23 C 0.57676(17) -0.1389(3) 1.09035(8) 0.0305(4) Uani 1 1 d .
H23A H 0.5375 -0.2260 1.1140 0.037 Uiso 1 1 calc R
C24 C 0.67697(17) -0.1964(3) 1.06000(8) 0.0299(4) Uani 1 1 d .
H24A H 0.7066 -0.3240 1.0627 0.036 Uiso 1 1 calc R
C25 C 0.73467(17) -0.0692(3) 1.02563(7) 0.0271(4) Uani 1 1 d .
H25A H 0.8031 -0.1116 1.0048 0.033 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
C14 N1 C1 122.08(15)
C14 N1 C4 124.10(14)
C1 N1 C4 113.19(14)
N1 C1 C2 105.01(14)
C1 C2 C3 104.46(14)
C2 C3 C4 105.62(15)
N1 C4 C3 102.98(14)
N1 C4 C5 112.70(15)
C3 C4 C5 114.92(15)
C13 C5 C4 116.04(15)
C13 C5 C6 101.34(14)
C4 C5 C6 117.97(15)
C7 C6 C5 103.92(15)
C8 C7 C6 102.54(15)
C9 C8 C13 120.62(18)
C9 C8 C7 129.61(18)
C13 C8 C7 109.74(16)
C10 C9 C8 118.49(18)
C9 C10 C11 120.78(18)
C10 C11 C12 121.28(18)
C11 C12 C13 117.82(18)
C12 C13 C8 120.98(17)
C12 C13 C5 128.74(17)
C8 C13 C5 110.27(16)
N1 C14 C19 121.07(16)
N1 C14 C15 122.42(16)
C19 C14 C15 116.51(16)
C16 C15 C14 121.12(17)
C15 C16 C17 122.48(17)
C18 C17 C16 115.80(16)
C18 C17 C20 122.23(16)
C16 C17 C20 121.95(16)
C19 C18 C17 122.66(17)
C18 C19 C14 121.44(17)
C21 C20 C25 116.98(17)
C21 C20 C17 121.83(16)
C25 C20 C17 121.18(16)
C22 C21 C20 121.75(18)
C23 C22 C21 120.18(18)
C24 C23 C22 119.21(18)
C23 C24 C25 120.46(18)
C24 C25 C20 121.41(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C14 1.371(2)
N1 C1 1.461(2)
N1 C4 1.463(2)
C1 C2 1.523(3)
C2 C3 1.526(3)
C3 C4 1.534(2)
C4 C5 1.540(3)
C5 C13 1.515(2)
C5 C6 1.546(3)
C6 C7 1.542(3)
C7 C8 1.504(3)
C8 C9 1.391(3)
C8 C13 1.399(3)
C9 C10 1.389(3)
C10 C11 1.391(3)
C11 C12 1.393(3)
C12 C13 1.394(2)
C14 C19 1.405(2)
C14 C15 1.407(2)
C15 C16 1.383(2)
C16 C17 1.399(2)
C17 C18 1.396(2)
C17 C20 1.479(2)
C18 C19 1.376(2)
C20 C21 1.394(2)
C20 C25 1.398(3)
C21 C22 1.386(3)
C22 C23 1.384(3)
C23 C24 1.380(3)
C24 C25 1.387(3)
