#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:13:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178426 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/47/4024743.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_4024743
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_sum            'C34 H46 N8 O2'
_chemical_formula_weight         598.79
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 90.77(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.199(3)
_cell_length_b                   11.393(5)
_cell_length_c                   21.935(5)
_cell_measurement_reflns_used    141
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      0.20
_cell_measurement_theta_min      0.01
_cell_volume                     3048.3(17)
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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    0.0875
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            1578
_diffrn_reflns_theta_full        20.81
_diffrn_reflns_theta_max         20.81
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0851
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.023
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1594P)²+0.8451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2071
_refine_ls_wR_factor_ref         0.2205
_reflns_number_gt                1089
_reflns_number_total             1578
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900755r_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/C
_cod_database_code               4024743
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, -z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7880(4) 0.0298(4) 0.7326(2) 0.0590(14) Uani 1 1 d . . .
N1 N 0.7992(4) 0.1970(4) 0.7916(2) 0.0414(14) Uani 1 1 d . . .
N2 N 0.9786(4) 0.2060(4) 0.8119(2) 0.0407(14) Uani 1 1 d . . .
N3 N 0.8646(4) 0.3143(4) 0.8772(3) 0.0469(15) Uani 1 1 d . . .
C5 C 0.8769(5) 0.2464(5) 0.8328(3) 0.0390(16) Uani 1 1 d . . .
H5 H 0.8707 0.1781 0.8597 0.047 Uiso 1 1 calc R . .
N4 N 1.0710(4) 0.2016(5) 0.8512(2) 0.0504(15) Uani 1 1 d . . .
C7 C 0.6681(5) 0.2647(5) 0.9018(3) 0.0441(17) Uani 1 1 d . . .
C8 C 0.6299(5) 0.2049(6) 0.8503(3) 0.0471(18) Uani 1 1 d . . .
C9 C 0.8409(5) 0.0998(6) 0.7629(3) 0.0474(18) Uani 1 1 d . . .
H9 H 0.8556 0.1465 0.7264 0.057 Uiso 1 1 calc R . .
C10 C 1.0539(6) 0.1227(7) 0.9019(3) 0.062(2) Uani 1 1 d . . .
H10A H 1.0006 0.1560 0.9294 0.074 Uiso 1 1 calc R . .
H10B H 1.1222 0.1115 0.9244 0.074 Uiso 1 1 calc R . .
C11 C 0.6836(5) 0.2281(6) 0.7899(3) 0.0483(18) Uani 1 1 d . . .
H11A H 0.6466 0.1828 0.7583 0.058 Uiso 1 1 calc R . .
H11B H 0.6760 0.3105 0.7797 0.058 Uiso 1 1 calc R . .
C12 C 0.9793(5) -0.0078(6) 0.8209(4) 0.052(2) Uani 1 1 d . . .
H12A H 0.9097 -0.0488 0.8225 0.063 Uiso 1 1 calc R . .
H12B H 1.0308 -0.0605 0.8017 0.063 Uiso 1 1 calc R . .
C13 C 0.9635(5) 0.0962(5) 0.7786(3) 0.0426(17) Uani 1 1 d . . .
C14 C 1.0135(6) 0.0075(7) 0.8782(4) 0.063(2) Uani 1 1 d . . .
H14A H 1.0720 -0.0487 0.8853 0.075 Uiso 1 1 calc R . .
H14B H 0.9534 -0.0159 0.9041 0.075 Uiso 1 1 calc R . .
C15 C 0.6215(6) 0.2409(6) 0.9574(3) 0.0559(19) Uani 1 1 d . . .
H15 H 0.6468 0.2796 0.9921 0.067 Uiso 1 1 calc R . .
C16 C 0.5447(6) 0.1241(6) 0.8550(4) 0.061(2) Uani 1 1 d . . .
H16 H 0.5192 0.0846 0.8205 0.073 Uiso 1 1 calc R . .
C17 C 0.7567(5) 0.3568(6) 0.8956(3) 0.0477(18) Uani 1 1 d . . .
H17A H 0.7319 0.4145 0.8660 0.057 Uiso 1 1 calc R . .
H17B H 0.7650 0.3967 0.9344 0.057 Uiso 1 1 calc R . .
C18 C 0.5378(6) 0.1601(7) 0.9620(4) 0.068(2) Uani 1 1 d . . .
H18 H 0.5080 0.1442 1.0000 0.081 Uiso 1 1 calc R . .
C19 C 0.4978(6) 0.1028(7) 0.9112(4) 0.073(2) Uani 1 1 d . . .
H19 H 0.4398 0.0503 0.9145 0.088 Uiso 1 1 calc R . .
C20 C 1.1175(5) 0.3174(6) 0.8642(3) 0.060(2) Uani 1 1 d . . .
H20A H 1.0719 0.3579 0.8934 0.073 Uiso 1 1 calc R . .
H20B H 1.1183 0.3635 0.8270 0.073 Uiso 1 1 calc R . .
C21 C 1.2648(8) 0.3622(12) 0.9391(5) 0.130(4) Uani 1 1 d . . .
H21A H 1.3401 0.3424 0.9472 0.195 Uiso 1 1 calc R . .
H21B H 1.2209 0.3385 0.9730 0.195 Uiso 1 1 calc R . .
H21C H 1.2583 0.4455 0.9335 0.195 Uiso 1 1 calc R . .
C22 C 1.2304(6) 0.3076(9) 0.8892(4) 0.086(3) Uani 1 1 d . . .
H22A H 1.2437 0.2246 0.8959 0.103 Uiso 1 1 calc R . .
H22B H 1.2789 0.3316 0.8568 0.103 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'
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
C9 N1 C5 111.3(5) . . ?
C9 N1 C11 123.3(5) . . ?
C5 N1 C11 124.0(5) . . ?
C5 N2 N4 120.9(5) . . ?
C5 N2 C13 109.8(5) . . ?
N4 N2 C13 111.7(4) . . ?
C5 N3 C17 122.3(5) . . ?
N3 C5 N2 124.7(6) . . ?
N3 C5 N1 130.9(6) . . ?
N2 C5 N1 104.3(5) . . ?
N2 N4 C10 111.7(5) . . ?
N2 N4 C20 113.0(5) . . ?
C10 N4 C20 118.0(6) . . ?
C15 C7 C8 118.9(6) . . ?
C15 C7 C17 121.3(6) . . ?
C8 C7 C17 119.8(6) . . ?
C16 C8 C7 120.3(6) . . ?
C16 C8 C11 120.9(7) . . ?
C7 C8 C11 118.8(6) . . ?
O1 C9 N1 125.5(6) . . ?
O1 C9 C13 127.8(6) . . ?
N1 C9 C13 106.6(6) . . ?
N4 C10 C14 109.2(6) . . ?
N1 C11 C8 111.6(5) . . ?
C14 C12 C13 120.8(6) . . ?
N2 C13 C12 110.4(5) . . ?
N2 C13 C9 101.8(5) . . ?
C12 C13 C9 105.9(5) . . ?
N2 C13 C13 109.6(3) . 6_757 ?
C12 C13 C13 115.3(4) . 6_757 ?
C9 C13 C13 112.9(6) . 6_757 ?
C12 C14 C10 122.9(7) . . ?
C7 C15 C18 120.7(7) . . ?
C19 C16 C8 119.8(7) . . ?
N3 C17 C7 116.2(5) . . ?
C15 C18 C19 120.8(7) . . ?
C18 C19 C16 119.4(7) . . ?
N4 C20 C22 111.1(7) . . ?
C21 C22 C20 123.6(9) . . ?
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
O1 C9 1.218(7) . ?
N1 C9 1.374(8) . ?
N1 C5 1.417(8) . ?
N1 C11 1.455(7) . ?
N2 C5 1.406(7) . ?
N2 N4 1.411(7) . ?
N2 C13 1.459(7) . ?
N3 C5 1.255(7) . ?
N3 C17 1.464(8) . ?
N4 C10 1.447(8) . ?
N4 C20 1.464(8) . ?
C7 C15 1.380(9) . ?
C7 C8 1.394(9) . ?
C7 C17 1.513(9) . ?
C8 C16 1.394(9) . ?
C8 C11 1.509(9) . ?
C9 C13 1.531(9) . ?
C10 C14 1.492(10) . ?
C12 C14 1.330(10) . ?
C12 C13 1.515(9) . ?
C13 C13 1.549(12) 6_757 ?
C15 C18 1.379(10) . ?
C16 C19 1.388(10) . ?
C18 C19 1.375(11) . ?
C20 C22 1.479(10) . ?
C21 C22 1.324(11) . ?
