#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/47/4024746.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_4024746
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            'C25 H28 Br2 N5 O3 Si'
_chemical_formula_weight         634.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 113.122(37)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   14.476(12)
_cell_length_b                   14.203(12)
_cell_length_c                   14.986(13)
_cell_measurement_reflns_used    139
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      0.2
_cell_measurement_theta_min      0.01
_cell_volume                     2833.7(42)
_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 0.987
_diffrn_measured_fraction_theta_max 0.987
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2936
_diffrn_reflns_theta_full        20.81
_diffrn_reflns_theta_max         20.81
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    2.938
_exptl_absorpt_correction_T_max  0.625
_exptl_absorpt_correction_T_min  0.439
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'HKL2000 v095.373'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.883
_refine_diff_density_rms         0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         2936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0728
_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)+(0.1956P)²+1.0957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2129
_refine_ls_wR_factor_ref         0.2384
_reflns_number_gt                2018
_reflns_number_total             2936
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900755r_si_005.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P21/a
_cod_original_formula_sum        'C25 H28 Br2 N5 O3 Si1'
_cod_database_code               4024746
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
Br1 Br 0.39847(12) 0.39627(11) -0.11765(10) 0.0875(7) Uani 1 1 d . . .
Br2 Br 0.66107(12) 0.33662(13) 0.00752(11) 0.0930(7) Uani 1 1 d . . .
Si3 Si 0.8301(4) 0.6024(4) 0.4678(3) 0.0963(15) Uani 1 1 d . . .
C1 C 0.4677(10) 0.3736(9) 0.0156(9) 0.062(3) Uani 1 1 d . . .
C2 C 0.4241(9) 0.3822(8) 0.0844(8) 0.060(3) Uani 1 1 d . . .
C3 C 0.5028(9) 0.3621(9) 0.1726(9) 0.064(3) Uani 1 1 d . . .
N5 N 0.5879(7) 0.3396(7) 0.1565(8) 0.065(3) Uani 1 1 d . . .
C4 C 0.5668(10) 0.3509(9) 0.0598(10) 0.064(3) Uani 1 1 d . . .
C5 C 0.6908(10) 0.3180(11) 0.2297(10) 0.078(4) Uani 1 1 d . . .
H5A H 0.6853 0.2904 0.2866 0.094 Uiso 1 1 calc R . .
H5B H 0.7220 0.2718 0.2027 0.094 Uiso 1 1 calc R . .
O21 O 0.7512(7) 0.3963(8) 0.2572(7) 0.089(3) Uani 1 1 d . . .
C6 C 0.7425(12) 0.4496(13) 0.3332(11) 0.100(5) Uani 1 1 d . . .
H6A H 0.7559 0.4099 0.3896 0.120 Uiso 1 1 calc R . .
H6B H 0.6748 0.4741 0.3130 0.120 Uiso 1 1 calc R . .
C7 C 0.8124(14) 0.5254(13) 0.3575(12) 0.118(6) Uani 1 1 d . . .
H7A H 0.7930 0.5665 0.3014 0.142 Uiso 1 1 calc R . .
H7B H 0.8775 0.4992 0.3670 0.142 Uiso 1 1 calc R . .
C8 C 0.8303(13) 0.5337(15) 0.5740(11) 0.123(6) Uani 1 1 d . . .
H8A H 0.8376 0.5760 0.6264 0.184 Uiso 1 1 calc R . .
H8B H 0.8852 0.4899 0.5944 0.184 Uiso 1 1 calc R . .
H8C H 0.7681 0.5000 0.5560 0.184 Uiso 1 1 calc R . .
C9 C 0.9537(13) 0.6594(14) 0.4864(15) 0.129(7) Uani 1 1 d . . .
H9A H 0.9473 0.6937 0.4291 0.194 Uiso 1 1 calc R . .
H9B H 1.0043 0.6118 0.4992 0.194 Uiso 1 1 calc R . .
H9C H 0.9725 0.7019 0.5405 0.194 Uiso 1 1 calc R . .
C10 C 0.7287(16) 0.7010(18) 0.4399(18) 0.173(10) Uani 1 1 d . . .
H10A H 0.7269 0.7373 0.3852 0.260 Uiso 1 1 calc R . .
H10B H 0.7452 0.7414 0.4954 0.260 Uiso 1 1 calc R . .
H10C H 0.6641 0.6729 0.4255 0.260 Uiso 1 1 calc R . .
C11 C 0.5007(10) 0.3537(11) 0.2725(10) 0.069(4) Uani 1 1 d . . .
O8 O 0.5549(8) 0.2959(8) 0.3311(7) 0.099(3) Uani 1 1 d . . .
N11 N 0.4371(7) 0.4104(7) 0.2947(7) 0.062(3) Uani 1 1 d . . .
C12 C 0.4396(10) 0.4109(9) 0.3945(8) 0.066(3) Uani 1 1 d . . .
H12A H 0.4727 0.3546 0.4290 0.079 Uiso 1 1 calc R . .
H12B H 0.3717 0.4122 0.3924 0.079 Uiso 1 1 calc R . .
C13 C 0.4971(9) 0.4985(9) 0.4463(8) 0.061(3) Uani 1 1 d . . .
C14 C 0.4427(9) 0.5861(9) 0.3909(8) 0.060(3) Uani 1 1 d . . .
H14A H 0.3786 0.5923 0.3967 0.072 Uiso 1 1 calc R . .
H14B H 0.4824 0.6416 0.4194 0.072 Uiso 1 1 calc R . .
C15 C 0.4253(9) 0.5803(9) 0.2837(8) 0.062(3) Uani 1 1 d . . .
H15 H 0.4863 0.6001 0.2754 0.074 Uiso 1 1 calc R . .
N14 N 0.3940(7) 0.4884(7) 0.2395(7) 0.060(3) Uani 1 1 d . . .
C16 C 0.2877(10) 0.4852(10) 0.1863(8) 0.059(3) Uani 1 1 d . . .
N4 N 0.2592(7) 0.5811(7) 0.1720(7) 0.060(3) Uani 1 1 d . . .
C17 C 0.3382(9) 0.6447(12) 0.2245(8) 0.066(4) Uani 1 1 d . . .
O6 O 0.3323(6) 0.7295(8) 0.2271(6) 0.077(3) Uani 1 1 d . . .
N20 N 0.2392(8) 0.4120(8) 0.1585(7) 0.060(3) Uani 1 1 d . . .
C18 C 0.1316(9) 0.4139(9) 0.0936(9) 0.067(3) Uani 1 1 d . . .
H18A H 0.1061 0.3499 0.0852 0.080 Uiso 1 1 calc R . .
H18B H 0.1253 0.4367 0.0305 0.080 Uiso 1 1 calc R . .
C19 C 0.0667(9) 0.4739(10) 0.1287(8) 0.063(3) Uani 1 1 d . . .
C20 C 0.0788(9) 0.5711(11) 0.1386(9) 0.069(4) Uani 1 1 d . . .
C21 C 0.1572(9) 0.6164(9) 0.1110(9) 0.066(4) Uani 1 1 d . . .
H21A H 0.1429 0.6032 0.0434 0.079 Uiso 1 1 calc R . .
H21B H 0.1551 0.6841 0.1185 0.079 Uiso 1 1 calc R . .
C22 C -0.0104(11) 0.4361(11) 0.1532(10) 0.086(4) Uani 1 1 d . . .
H22 H -0.0197 0.3712 0.1512 0.104 Uiso 1 1 calc R . .
C23 C -0.0704(10) 0.4912(14) 0.1793(11) 0.090(5) Uani 1 1 d . . .
H23 H -0.1210 0.4630 0.1935 0.109 Uiso 1 1 calc R . .
C24 C -0.0614(12) 0.5827(13) 0.1858(11) 0.087(4) Uani 1 1 d . . .
H24 H -0.1063 0.6182 0.2023 0.104 Uiso 1 1 calc R . .
C25 C 0.0141(12) 0.6264(13) 0.1683(11) 0.096(5) Uani 1 1 d . . .
H25 H 0.0229 0.6912 0.1758 0.115 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C8 Si3 C9 114.5(9) . . ?
C8 Si3 C7 113.2(9) . . ?
C9 Si3 C7 99.9(8) . . ?
C8 Si3 C10 107.9(10) . . ?
C9 Si3 C10 108.3(10) . . ?
C7 Si3 C10 113.0(10) . . ?
C4 C1 C2 110.6(11) . . ?
C4 C1 Br1 125.4(10) . . ?
C2 C1 Br1 123.9(10) . . ?
C3 C2 C1 104.0(11) . . ?
N5 C3 C2 109.6(11) . . ?
N5 C3 C11 121.3(11) . . ?
C2 C3 C11 128.8(12) . . ?
C4 N5 C3 108.3(11) . . ?
C4 N5 C5 123.1(11) . . ?
C3 N5 C5 128.3(11) . . ?
C1 C4 N5 107.4(11) . . ?
C1 C4 Br2 129.6(10) . . ?
N5 C4 Br2 123.1(10) . . ?
O21 C5 N5 112.8(12) . . ?
C5 O21 C6 115.3(11) . . ?
O21 C6 C7 109.4(13) . . ?
C6 C7 Si3 119.6(13) . . ?
O8 C11 N11 121.5(11) . . ?
O8 C11 C3 120.2(12) . . ?
N11 C11 C3 118.3(12) . . ?
C11 N11 N14 121.3(10) . . ?
C11 N11 C12 120.0(10) . . ?
N14 N11 C12 115.4(9) . . ?
N11 C12 C13 108.0(10) . . ?
C12 C13 C14 109.0(9) . . ?
C12 C13 C13 109.8(13) . 3_666 ?
C14 C13 C13 109.9(12) . 3_666 ?
C15 C14 C13 111.3(10) . . ?
N14 C15 C17 103.5(10) . . ?
N14 C15 C14 114.9(10) . . ?
C17 C15 C14 109.6(10) . . ?
N11 N14 C16 116.3(10) . . ?
N11 N14 C15 117.5(9) . . ?
C16 N14 C15 110.9(10) . . ?
N20 C16 N4 131.8(12) . . ?
N20 C16 N14 124.2(12) . . ?
N4 C16 N14 103.9(11) . . ?
C16 N4 C17 113.7(11) . . ?
C16 N4 C21 125.3(10) . . ?
C17 N4 C21 120.9(11) . . ?
O6 C17 N4 126.7(12) . . ?
O6 C17 C15 129.0(12) . . ?
N4 C17 C15 104.0(12) . . ?
C16 N20 C18 121.5(11) . . ?
N20 C18 C19 114.9(10) . . ?
C20 C19 C22 115.4(13) . . ?
C20 C19 C18 121.9(12) . . ?
C22 C19 C18 122.7(13) . . ?
C19 C20 C25 120.6(13) . . ?
C19 C20 C21 118.3(13) . . ?
C25 C20 C21 121.0(14) . . ?
N4 C21 C20 111.3(10) . . ?
C23 C22 C19 121.6(15) . . ?
C24 C23 C22 123.2(16) . . ?
C23 C24 C25 120.0(15) . . ?
C24 C25 C20 119.0(16) . . ?
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
Br1 C1 1.877(12) . ?
Br2 C4 1.833(13) . ?
Si3 C8 1.866(17) . ?
Si3 C9 1.883(17) . ?
Si3 C7 1.913(17) . ?
Si3 C10 1.95(2) . ?
C1 C4 1.362(17) . ?
C1 C2 1.410(17) . ?
C2 C3 1.394(16) . ?
C3 N5 1.382(15) . ?
C3 C11 1.514(18) . ?
N5 C4 1.368(16) . ?
N5 C5 1.495(16) . ?
C5 O21 1.374(16) . ?
O21 C6 1.415(17) . ?
C6 C7 1.42(2) . ?
C11 O8 1.232(15) . ?
C11 N11 1.360(16) . ?
N11 N14 1.376(13) . ?
N11 C12 1.483(14) . ?
C12 C13 1.528(17) . ?
C13 C14 1.531(16) . ?
C13 C13 1.58(2) 3_666 ?
C14 C15 1.527(16) . ?
C15 N14 1.454(15) . ?
C15 C17 1.529(18) . ?
N14 C16 1.430(15) . ?
C16 N20 1.231(15) . ?
C16 N4 1.416(16) . ?
N4 C17 1.427(17) . ?
N4 C21 1.485(15) . ?
C17 O6 1.209(16) . ?
N20 C18 1.477(16) . ?
C18 C19 1.508(17) . ?
C19 C20 1.393(18) . ?
C19 C22 1.411(18) . ?
C20 C25 1.42(2) . ?
C20 C21 1.496(18) . ?
C22 C23 1.34(2) . ?
C23 C24 1.31(2) . ?
C24 C25 1.37(2) . ?
