#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:13:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178426 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/47/4024742.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_4024742
loop_
_publ_author_name
'Qingyi Li'
'Paul Hurley'
'Hui Ding'
'Andrew G. Roberts'
'Radha Akella'
'Patrick G. Harran'
_publ_section_title
;
Exploring Symmetry-Based Logic for a Synthesis of Palau'amine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5909
_journal_page_last               5919
_journal_paper_doi               10.1021/jo900755r
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C34 H34 N8 O2'
_chemical_formula_sum            'C34 H34 N8 O2'
_chemical_formula_weight         586.70
_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                101.7740(18)
_cell_angle_beta                 101.7910(16)
_cell_angle_gamma                97.4190(19)
_cell_formula_units_Z            2
_cell_length_a                   10.5970(4)
_cell_length_b                   11.4680(5)
_cell_length_c                   13.4690(7)
_cell_measurement_reflns_used    142
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      0.2
_cell_measurement_theta_min      0.0
_cell_volume                     1543.47(12)
_computing_cell_refinement       'HKL2000 v095.373'
_computing_data_collection       'collect, Nonius 1999'
_computing_data_reduction        'HKL2000 v095.373'
_computing_publication_material  'XCIF (Sheldrick and Bruker 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       Collect
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0751
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5686
_diffrn_reflns_theta_full        25.81
_diffrn_reflns_theta_max         25.81
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         5686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0524
_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)+(0.0839P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                3061
_reflns_number_total             5686
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900755r_si_001.cif
_cod_data_source_block           shelxl
_cod_database_code               4024742
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
_atom_site_disorder_assembly
_atom_site_disorder_group
H1 H 0.318(3) 0.892(3) 0.539(3) 0.082(9) Uiso 1 1 d . . .
H2 H 0.151(3) 0.727(3) 0.518(3) 0.090(10) Uiso 1 1 d . . .
H3 H -0.003(3) 0.647(3) 0.359(2) 0.098(11) Uiso 1 1 d . . .
H4 H 0.007(3) 0.730(2) 0.209(2) 0.074(8) Uiso 1 1 d . . .
H71 H 0.419(2) 1.0503(19) 0.4709(19) 0.042(6) Uiso 1 1 d . . .
H72 H 0.327(3) 1.087(2) 0.3722(19) 0.064(8) Uiso 1 1 d . . .
H91 H 0.181(3) 1.012(3) 0.216(2) 0.067(8) Uiso 1 1 d . . .
H92 H 0.102(3) 0.876(2) 0.135(2) 0.064(8) Uiso 1 1 d . . .
H121 H 0.665(2) 0.757(2) 0.1510(17) 0.049(7) Uiso 1 1 d . . .
H122 H 0.798(3) 0.846(2) 0.1675(19) 0.061(8) Uiso 1 1 d . . .
H13 H 0.701(2) 0.917(2) 0.0189(19) 0.063(8) Uiso 1 1 d . . .
H14 H 0.459(2) 0.8002(19) -0.0739(19) 0.044(6) Uiso 1 1 d . . .
H151 H 0.672(2) 1.102(2) 0.266(2) 0.056(7) Uiso 1 1 d . . .
H152 H 0.717(2) 1.073(2) 0.158(2) 0.058(7) Uiso 1 1 d . . .
H16 H 0.878(3) 1.026(2) 0.345(2) 0.067(8) Uiso 1 1 d . . .
H171 H 1.050(4) 1.143(3) 0.298(2) 0.090(10) Uiso 1 1 d . . .
H172 H 0.944(6) 1.149(5) 0.183(5) 0.20(3) Uiso 1 1 d . . .
H19 H 0.894(2) 0.842(2) -0.0453(17) 0.050(7) Uiso 1 1 d . . .
H20 H 1.016(3) 0.695(2) -0.016(2) 0.069(8) Uiso 1 1 d . . .
H211 H 0.861(2) 0.496(2) -0.0544(18) 0.047(6) Uiso 1 1 d . . .
H212 H 0.932(3) 0.554(2) 0.071(2) 0.063(8) Uiso 1 1 d . . .
H221 H 0.587(3) 0.493(2) 0.0627(19) 0.064(8) Uiso 1 1 d . . .
H222 H 0.685(3) 0.396(3) 0.018(2) 0.065(8) Uiso 1 1 d . . .
H23 H 0.742(3) 0.553(3) 0.225(3) 0.095(11) Uiso 1 1 d . . .
H241 H 0.840(3) 0.406(3) 0.281(3) 0.091(10) Uiso 1 1 d . . .
H242 H 0.807(3) 0.320(3) 0.153(3) 0.104(11) Uiso 1 1 d . . .
H271 H 0.590(3) 0.283(3) -0.282(2) 0.080(9) Uiso 1 1 d . . .
H272 H 0.662(3) 0.394(3) -0.317(3) 0.099(12) Uiso 1 1 d . . .
H301 H 0.640(3) 0.580(3) -0.357(2) 0.081(10) Uiso 1 1 d . . .
H302 H 0.539(3) 0.674(3) -0.354(2) 0.079(9) Uiso 1 1 d . . .
H31 H 0.367(3) 0.200(3) -0.372(2) 0.095(11) Uiso 1 1 d . . .
H32 H 0.168(4) 0.229(4) -0.481(3) 0.125(14) Uiso 1 1 d . . .
H33 H 0.151(4) 0.423(3) -0.516(3) 0.133(15) Uiso 1 1 d . . .
H34 H 0.329(3) 0.585(3) -0.449(2) 0.078(10) Uiso 1 1 d . . .
C1 C 0.2543(3) 0.8596(3) 0.4703(2) 0.0632(8) Uani 1 1 d . . .
C2 C 0.1572(3) 0.7623(3) 0.4592(3) 0.0759(9) Uani 1 1 d . . .
C3 C 0.0676(3) 0.7139(3) 0.3651(3) 0.0782(10) Uani 1 1 d . . .
C4 C 0.0747(3) 0.7662(3) 0.2810(2) 0.0641(8) Uani 1 1 d . . .
C5 C 0.1713(2) 0.8635(2) 0.29116(19) 0.0511(7) Uani 1 1 d . . .
C6 C 0.2623(3) 0.9113(2) 0.3868(2) 0.0519(7) Uani 1 1 d . . .
C7 C 0.3693(3) 1.0165(2) 0.3959(2) 0.0539(7) Uani 1 1 d . . .
C8 C 0.4318(2) 0.9391(2) 0.24030(19) 0.0426(6) Uani 1 1 d . . .
C9 C 0.1824(3) 0.9195(3) 0.2008(2) 0.0521(7) Uani 1 1 d . . .
C10 C 0.3133(3) 0.8669(2) 0.0696(2) 0.0446(6) Uani 1 1 d . . .
C11 C 0.4535(2) 0.86795(19) 0.07261(18) 0.0429(6) Uani 1 1 d . . .
C12 C 0.6991(3) 0.8332(3) 0.1416(2) 0.0493(7) Uani 1 1 d . . .
C13 C 0.6587(3) 0.8384(2) 0.02616(18) 0.0455(6) Uani 1 1 d . . .
C14 C 0.5139(3) 0.8314(2) -0.0026(2) 0.0463(6) Uani 1 1 d . . .
C15 C 0.7192(3) 1.0494(2) 0.2253(2) 0.0506(7) Uani 1 1 d . . .
C16 C 0.8581(3) 1.0686(3) 0.2838(2) 0.0657(8) Uani 1 1 d . . .
C17 C 0.9569(4) 1.1246(4) 0.2564(4) 0.0953(12) Uani 1 1 d . . .
O1 O 0.22041(18) 0.83938(16) -0.00620(13) 0.0586(5) Uani 1 1 d . . .
N1 N 0.46844(19) 0.98469(17) 0.33752(15) 0.0481(5) Uani 1 1 d . . .
N2 N 0.30690(19) 0.90565(16) 0.17113(15) 0.0443(5) Uani 1 1 d . . .
N3 N 0.51711(19) 0.91250(18) 0.17668(15) 0.0490(5) Uani 1 1 d . . .
N4 N 0.65430(19) 0.92375(17) 0.21379(15) 0.0465(5) Uani 1 1 d . . .
C18 C 0.7072(2) 0.7433(2) -0.04813(18) 0.0441(6) Uani 1 1 d . . .
C19 C 0.8554(3) 0.7646(3) -0.0339(2) 0.0552(7) Uani 1 1 d . . .
C20 C 0.9252(3) 0.6805(3) -0.0166(2) 0.0601(8) Uani 1 1 d . . .
C21 C 0.8691(3) 0.5660(3) 0.0061(3) 0.0556(7) Uani 1 1 d . . .
C22 C 0.6810(3) 0.4773(3) 0.0653(2) 0.0540(7) Uani 1 1 d . . .
C23 C 0.7467(3) 0.4839(3) 0.1758(2) 0.0608(8) Uani 1 1 d . . .
C24 C 0.8010(4) 0.3985(3) 0.2076(3) 0.0786(10) Uani 1 1 d . . .
C25 C 0.6291(2) 0.5461(2) -0.15158(18) 0.0442(6) Uani 1 1 d . . .
C26 C 0.6513(3) 0.7436(2) -0.16167(19) 0.0524(7) Uani 1 1 d . . .
C27 C 0.5910(4) 0.3660(3) -0.2838(2) 0.0664(9) Uani 1 1 d . . .
C28 C 0.4645(3) 0.3797(2) -0.3498(2) 0.0586(7) Uani 1 1 d . . .
C29 C 0.4503(3) 0.4915(2) -0.3719(2) 0.0601(8) Uani 1 1 d . . .
C30 C 0.5626(4) 0.5967(3) -0.3314(2) 0.0664(8) Uani 1 1 d . . .
C31 C 0.3610(4) 0.2829(3) -0.3888(2) 0.0751(9) Uani 1 1 d . . .
C32 C 0.2459(4) 0.2956(5) -0.4500(3) 0.0902(12) Uani 1 1 d . . .
C33 C 0.2309(4) 0.4059(5) -0.4730(3) 0.0898(12) Uani 1 1 d . . .
C34 C 0.3334(4) 0.5048(4) -0.4333(2) 0.0788(10) Uani 1 1 d . . .
O2 O 0.6492(2) 0.83284(16) -0.19768(14) 0.0727(6) Uani 1 1 d . . .
N5 N 0.74341(18) 0.57945(17) 0.03133(15) 0.0445(5) Uani 1 1 d . . .
N6 N 0.65927(18) 0.61738(16) -0.04830(15) 0.0415(5) Uani 1 1 d . . .
N7 N 0.6212(2) 0.43286(18) -0.17420(16) 0.0562(6) Uani 1 1 d . . .
N8 N 0.6089(2) 0.62717(17) -0.21667(15) 0.0515(6) 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'
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'
H H 0.0000 0.0000 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.2(3) . . ?
C3 C2 C1 120.8(3) . . ?
C2 C3 C4 119.1(3) . . ?
C5 C4 C3 120.5(3) . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 C9 121.4(2) . . ?
C6 C5 C9 118.8(2) . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 C7 121.5(3) . . ?
C5 C6 C7 119.1(2) . . ?
N1 C7 C6 113.9(2) . . ?
N1 C8 N3 123.8(2) . . ?
N1 C8 N2 132.1(2) . . ?
N3 C8 N2 104.00(19) . . ?
N2 C9 C5 110.7(2) . . ?
O1 C10 N2 125.7(2) . . ?
O1 C10 C11 128.5(2) . . ?
N2 C10 C11 105.7(2) . . ?
C14 C11 N3 123.9(2) . . ?
C14 C11 C10 131.1(2) . . ?
N3 C11 C10 105.0(2) . . ?
N4 C12 C13 114.3(2) . . ?
C14 C13 C18 113.1(2) . . ?
C14 C13 C12 108.2(2) . . ?
C18 C13 C12 113.6(2) . . ?
C11 C14 C13 118.6(2) . . ?
N4 C15 C16 110.4(2) . . ?
C17 C16 C15 124.2(4) . . ?
C8 N1 C7 119.0(2) . . ?
C10 N2 C8 112.4(2) . . ?
C10 N2 C9 122.3(2) . . ?
C8 N2 C9 125.1(2) . . ?
C11 N3 C8 112.8(2) . . ?
C11 N3 N4 122.93(19) . . ?
C8 N3 N4 124.17(19) . . ?
N3 N4 C12 107.62(19) . . ?
N3 N4 C15 109.94(19) . . ?
C12 N4 C15 113.9(2) . . ?
N6 C18 C19 110.0(2) . . ?
N6 C18 C26 100.83(18) . . ?
C19 C18 C26 105.4(2) . . ?
N6 C18 C13 114.67(18) . . ?
C19 C18 C13 113.8(2) . . ?
C26 C18 C13 111.0(2) . . ?
C20 C19 C18 122.1(3) . . ?
C19 C20 C21 122.5(3) . . ?
N5 C21 C20 108.4(2) . . ?
N5 C22 C23 109.4(2) . . ?
C24 C23 C22 124.6(3) . . ?
N7 C25 N8 130.4(2) . . ?
N7 C25 N6 123.7(2) . . ?
N8 C25 N6 105.85(19) . . ?
O2 C26 N8 125.8(2) . . ?
O2 C26 C18 125.9(2) . . ?
N8 C26 C18 108.2(2) . . ?
N7 C27 C28 115.4(2) . . ?
C31 C28 C29 119.6(3) . . ?
C31 C28 C27 120.9(3) . . ?
C29 C28 C27 119.5(3) . . ?
C34 C29 C28 119.8(3) . . ?
C34 C29 C30 120.1(3) . . ?
C28 C29 C30 120.1(3) . . ?
N8 C30 C29 113.0(2) . . ?
C32 C31 C28 120.7(4) . . ?
C31 C32 C33 120.2(4) . . ?
C32 C33 C34 119.9(4) . . ?
C29 C34 C33 119.8(4) . . ?
N6 N5 C21 111.3(2) . . ?
N6 N5 C22 114.40(18) . . ?
C21 N5 C22 114.9(2) . . ?
C25 N6 N5 118.69(18) . . ?
C25 N6 C18 109.11(17) . . ?
N5 N6 C18 110.67(17) . . ?
C25 N7 C27 120.1(2) . . ?
C26 N8 C25 111.2(2) . . ?
C26 N8 C30 121.2(2) . . ?
C25 N8 C30 127.3(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(4) . ?
C1 C6 1.386(4) . ?
C2 C3 1.378(5) . ?
C3 C4 1.396(4) . ?
C4 C5 1.377(4) . ?
C5 C6 1.400(3) . ?
C5 C9 1.505(4) . ?
C6 C7 1.512(4) . ?
C7 N1 1.474(3) . ?
C8 N1 1.265(3) . ?
C8 N3 1.388(3) . ?
C8 N2 1.409(3) . ?
C9 N2 1.473(3) . ?
C10 O1 1.220(3) . ?
C10 N2 1.367(3) . ?
C10 C11 1.476(4) . ?
C11 C14 1.331(3) . ?
C11 N3 1.383(3) . ?
C12 N4 1.467(3) . ?
C12 C13 1.542(4) . ?
C13 C14 1.492(4) . ?
C13 C18 1.537(3) . ?
C15 N4 1.477(3) . ?
C15 C16 1.485(4) . ?
C16 C17 1.314(5) . ?
N3 N4 1.417(3) . ?
C18 N6 1.467(3) . ?
C18 C19 1.523(4) . ?
C18 C26 1.524(3) . ?
C19 C20 1.318(4) . ?
C20 C21 1.486(4) . ?
C21 N5 1.459(3) . ?
C22 N5 1.470(3) . ?
C22 C23 1.492(4) . ?
C23 C24 1.300(4) . ?
C25 N7 1.259(3) . ?
C25 N8 1.409(3) . ?
C25 N6 1.411(3) . ?
C26 O2 1.220(3) . ?
C26 N8 1.356(3) . ?
C27 N7 1.467(3) . ?
C27 C28 1.495(4) . ?
C28 C31 1.386(4) . ?
C28 C29 1.394(4) . ?
C29 C34 1.386(4) . ?
C29 C30 1.505(4) . ?
C30 N8 1.476(3) . ?
C31 C32 1.369(5) . ?
C32 C33 1.383(5) . ?
C33 C34 1.396(5) . ?
N5 N6 1.426(3) . ?
