#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:55:18 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178829 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/83/4108342.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_4108342
loop_
_publ_author_name
'Edward C. Lis'
'Rebecca J. Salomon'
'Michal Sabat'
'William H. Myers'
'W. Dean Harman'
_publ_section_title
;
 Synthesis of 1-Oxadecalins from Anisole Promoted by Tungsten
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12472
_journal_page_last               12476
_journal_paper_doi               10.1021/ja803605m
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C28 H37 B Cl2 N7 O3 P S W'
_chemical_formula_weight         848.24
_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                 107.163(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3422(13)
_cell_length_b                   20.007(2)
_cell_length_c                   14.4645(15)
_cell_measurement_reflns_used    5008
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.990
_cell_measurement_theta_min      2.274
_cell_volume                     3412.7(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0940
_diffrn_reflns_av_sigmaI/netI    0.1308
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44345
_diffrn_reflns_theta_full        32.58
_diffrn_reflns_theta_max         32.58
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    3.690
_exptl_absorpt_correction_T_max  0.801925
_exptl_absorpt_correction_T_min  0.479380
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS '
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_description       needle
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         2.569
_refine_diff_density_min         -1.019
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         12275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.824
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0365P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                6089
_reflns_number_total             12275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja803605m_si_004.cif
_cod_data_source_block           C28H37BN7O3PSCl2W
_cod_database_code               4108342
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
W W 0.706985(17) 0.759771(10) 0.846357(15) 0.03618(7) Uani 1 1 d .
Cl1 Cl 0.2343(2) 0.92436(15) 0.7393(3) 0.1558(12) Uani 1 1 d .
Cl2 Cl 0.0995(3) 0.96649(17) 0.8631(3) 0.1733(14) Uani 1 1 d .
S1 S 0.27359(13) 0.69286(8) 0.78076(12) 0.0582(4) Uani 1 1 d .
P1 P 0.64613(13) 0.88067(7) 0.84398(11) 0.0463(4) Uani 1 1 d .
O1 O 0.6069(3) 0.5845(2) 0.6883(3) 0.0705(13) Uani 1 1 d .
O2 O 0.3854(4) 0.5756(2) 0.5578(3) 0.0772(14) Uani 1 1 d .
H2O2 H 0.4509 0.5633 0.5827 0.116 Uiso 1 1 calc R
O3 O 0.5898(3) 0.7164(2) 0.9898(3) 0.0630(11) Uani 1 1 d .
N1 N 0.8409(4) 0.7980(2) 0.9728(3) 0.0430(11) Uani 1 1 d .
N2 N 0.9516(4) 0.7989(3) 0.9782(3) 0.0555(13) Uani 1 1 d .
N3 N 0.8314(4) 0.6759(2) 0.8745(3) 0.0457(11) Uani 1 1 d .
N4 N 0.9440(4) 0.6876(2) 0.8993(3) 0.0519(12) Uani 1 1 d .
N5 N 0.8224(4) 0.7968(2) 0.7620(3) 0.0426(10) Uani 1 1 d .
N6 N 0.9374(4) 0.7921(2) 0.8015(3) 0.0516(12) Uani 1 1 d .
N7 N 0.6329(3) 0.7328(2) 0.9270(3) 0.0427(10) Uani 1 1 d .
C1 C 0.5645(4) 0.6375(3) 0.7084(4) 0.0462(14) Uani 1 1 d .
C2 C 0.6191(5) 0.7010(3) 0.7142(4) 0.0429(14) Uani 1 1 d .
C3 C 0.5582(4) 0.7619(3) 0.7156(4) 0.0430(13) Uani 1 1 d .
C4 C 0.4348(4) 0.7576(3) 0.7165(4) 0.0439(12) Uani 1 1 d .
H4 H 0.4179 0.7963 0.7514 0.053 Uiso 1 1 calc R
C5 C 0.4171(4) 0.6937(2) 0.7685(4) 0.0419(13) Uani 1 1 d .
H5 H 0.4712 0.6940 0.8336 0.050 Uiso 1 1 calc R
C6 C 0.4438(4) 0.6341(3) 0.7146(4) 0.0457(13) Uani 1 1 d .
H6 H 0.4341 0.5930 0.7481 0.055 Uiso 1 1 calc R
C7 C 0.3623(5) 0.6326(3) 0.6088(4) 0.0557(16) Uani 1 1 d .
H7A H 0.2846 0.6282 0.6126 0.067 Uiso 1 1 calc R
C8 C 0.3687(5) 0.6967(3) 0.5558(4) 0.0600(17) Uani 1 1 d .
H8A H 0.3103 0.6963 0.4938 0.072 Uiso 1 1 calc R
H8B H 0.4417 0.6990 0.5434 0.072 Uiso 1 1 calc R
C9 C 0.3537(5) 0.7579(3) 0.6118(4) 0.0574(16) Uani 1 1 d .
H9A H 0.2759 0.7599 0.6140 0.069 Uiso 1 1 calc R
H9B H 0.3678 0.7976 0.5786 0.069 Uiso 1 1 calc R
C10 C 0.2786(5) 0.6155(3) 0.8434(5) 0.0547(16) Uani 1 1 d .
C11 C 0.1938(5) 0.5691(3) 0.8042(5) 0.0653(18) Uani 1 1 d .
H11 H 0.1395 0.5777 0.7455 0.078 Uiso 1 1 calc R
C12 C 0.1906(7) 0.5099(4) 0.8535(6) 0.083(2) Uani 1 1 d .
H12 H 0.1332 0.4790 0.8279 0.099 Uiso 1 1 calc R
C13 C 0.2703(8) 0.4967(4) 0.9384(6) 0.088(2) Uani 1 1 d .
H13 H 0.2674 0.4569 0.9709 0.105 Uiso 1 1 calc R
C14 C 0.3566(7) 0.5425(4) 0.9771(5) 0.090(3) Uani 1 1 d .
H14 H 0.4120 0.5334 1.0351 0.108 Uiso 1 1 calc R
C15 C 0.3589(7) 0.6016(4) 0.9285(5) 0.076(2) Uani 1 1 d .
H15 H 0.4162 0.6324 0.9543 0.091 Uiso 1 1 calc R
C16 C 1.0111(6) 0.8230(3) 1.0654(5) 0.0665(18) Uani 1 1 d .
H16 H 1.0896 0.8272 1.0874 0.080 Uiso 1 1 calc R
C17 C 0.9384(6) 0.8402(3) 1.1163(4) 0.0681(19) Uani 1 1 d .
H17 H 0.9562 0.8593 1.1776 0.082 Uiso 1 1 calc R
C18 C 0.8317(5) 0.8228(3) 1.0563(4) 0.0500(14) Uani 1 1 d .
H18 H 0.7642 0.8277 1.0718 0.060 Uiso 1 1 calc R
C19 C 0.9988(6) 0.6295(4) 0.9172(5) 0.0675(19) Uani 1 1 d .
H19 H 1.0772 0.6244 0.9346 0.081 Uiso 1 1 calc R
C20 C 0.9241(6) 0.5796(3) 0.9065(5) 0.0697(19) Uani 1 1 d .
H20 H 0.9393 0.5342 0.9156 0.084 Uiso 1 1 calc R
C21 C 0.8189(5) 0.6106(3) 0.8786(4) 0.0549(15) Uani 1 1 d .
H21 H 0.7496 0.5885 0.8647 0.066 Uiso 1 1 calc R
C22 C 0.9874(5) 0.8155(3) 0.7383(5) 0.0586(17) Uani 1 1 d .
H22 H 1.0653 0.8179 0.7482 0.070 Uiso 1 1 calc R
C23 C 0.9069(6) 0.8351(3) 0.6571(5) 0.0589(16) Uani 1 1 d .
H23 H 0.9179 0.8530 0.6012 0.071 Uiso 1 1 calc R
C24 C 0.8062(5) 0.8229(3) 0.6750(4) 0.0474(14) Uani 1 1 d .
H24 H 0.7354 0.8318 0.6317 0.057 Uiso 1 1 calc R
C25 C 0.5636(5) 0.9194(3) 0.7320(4) 0.0641(18) Uani 1 1 d .
H25A H 0.5505 0.9655 0.7437 0.096 Uiso 1 1 calc R
H25B H 0.4923 0.8967 0.7080 0.096 Uiso 1 1 calc R
H25C H 0.6045 0.9166 0.6850 0.096 Uiso 1 1 calc R
C26 C 0.5608(6) 0.8980(3) 0.9237(5) 0.0698(19) Uani 1 1 d .
H26A H 0.4948 0.8700 0.9067 0.105 Uiso 1 1 calc R
H26B H 0.5380 0.9441 0.9174 0.105 Uiso 1 1 calc R
H26C H 0.6045 0.8893 0.9894 0.105 Uiso 1 1 calc R
C27 C 0.7640(5) 0.9392(3) 0.8814(5) 0.0657(18) Uani 1 1 d .
H27A H 0.7352 0.9840 0.8785 0.099 Uiso 1 1 calc R
H27B H 0.8106 0.9353 0.8390 0.099 Uiso 1 1 calc R
H27C H 0.8085 0.9293 0.9465 0.099 Uiso 1 1 calc R
C28 C 0.2249(8) 0.9729(5) 0.8408(6) 0.125(4) Uani 1 1 d .
H28A H 0.2843 0.9587 0.8978 0.150 Uiso 1 1 calc R
H28B H 0.2384 1.0195 0.8291 0.150 Uiso 1 1 calc R
B1 B 0.9902(5) 0.7608(4) 0.9013(5) 0.0562(18) Uani 1 1 d .
H1B H 1.083(4) 0.766(2) 0.919(3) 0.042(13) Uiso 1 1 d .
H2 H 0.661(4) 0.701(3) 0.682(4) 0.041(16) Uiso 1 1 d .
H3 H 0.561(5) 0.785(3) 0.668(4) 0.07(2) Uiso 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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
W W -0.8490 6.8722 '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
N7 W N1 88.04(17)
N7 W C3 96.3(2)
N1 W C3 158.5(2)
N7 W N3 96.44(18)
N1 W N3 78.58(16)
C3 W N3 121.58(19)
N7 W C2 100.9(2)
N1 W C2 161.21(19)
C3 W C2 37.6(2)
N3 W C2 83.98(19)
N7 W N5 171.94(17)
N1 W N5 84.05(15)
C3 W N5 91.66(19)
N3 W N5 80.49(16)
C2 W N5 86.24(18)
N7 W P1 95.27(14)
N1 W P1 80.03(12)
C3 W P1 78.59(16)
N3 W P1 155.18(12)
C2 W P1 115.09(16)
N5 W P1 84.91(12)
C10 S1 C5 99.6(3)
C26 P1 C25 102.0(3)
C26 P1 C27 104.5(3)
C25 P1 C27 100.3(3)
C26 P1 W 113.6(2)
C25 P1 W 120.5(2)
C27 P1 W 113.8(2)
C18 N1 N2 107.2(5)
C18 N1 W 129.2(4)
N2 N1 W 123.6(3)
N1 N2 C16 108.9(5)
N1 N2 B1 118.5(4)
C16 N2 B1 131.0(5)
C21 N3 N4 106.6(5)
C21 N3 W 132.1(4)
N4 N3 W 121.2(3)
C19 N4 N3 108.9(5)
C19 N4 B1 130.6(5)
N3 N4 B1 120.5(4)
C24 N5 N6 105.7(4)
C24 N5 W 134.6(4)
N6 N5 W 119.7(3)
C22 N6 N5 108.9(5)
C22 N6 B1 129.5(5)
N5 N6 B1 121.5(4)
O3 N7 W 174.0(4)
O1 C1 C2 122.9(5)
O1 C1 C6 117.4(5)
C2 C1 C6 119.3(5)
C1 C2 C3 121.0(5)
C1 C2 W 128.2(4)
C3 C2 W 70.4(3)
C2 C3 C4 118.7(5)
C2 C3 W 72.0(3)
C4 C3 W 124.7(4)
C3 C4 C5 109.7(4)
C3 C4 C9 110.5(5)
C5 C4 C9 109.8(4)
C6 C5 C4 108.7(4)
C6 C5 S1 114.0(4)
C4 C5 S1 109.7(3)
C5 C6 C1 111.2(4)
C5 C6 C7 110.2(4)
C1 C6 C7 107.6(4)
O2 C7 C8 111.4(5)
O2 C7 C6 110.6(5)
C8 C7 C6 111.5(5)
C7 C8 C9 112.5(5)
C8 C9 C4 112.0(5)
C15 C10 C11 119.4(6)
C15 C10 S1 122.9(5)
C11 C10 S1 117.6(5)
C10 C11 C12 119.6(7)
C13 C12 C11 120.5(7)
C12 C13 C14 120.1(7)
C15 C14 C13 119.2(8)
C10 C15 C14 121.1(7)
N2 C16 C17 109.4(6)
C16 C17 C18 104.7(5)
N1 C18 C17 109.8(5)
N4 C19 C20 109.6(6)
C19 C20 C21 104.8(6)
N3 C21 C20 110.1(6)
N6 C22 C23 109.1(5)
C22 C23 C24 105.1(6)
N5 C24 C23 111.2(6)
Cl2 C28 Cl1 113.7(5)
N6 B1 N2 110.0(5)
N6 B1 N4 108.2(5)
N2 B1 N4 106.7(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
W N7 1.766(5)
W N1 2.208(4)
W C3 2.214(5)
W N3 2.229(4)
W C2 2.234(5)
W N5 2.256(4)
W P1 2.5301(15)
Cl1 C28 1.791(9)
Cl2 C28 1.677(9)
S1 C10 1.785(6)
S1 C5 1.832(5)
P1 C26 1.810(6)
P1 C25 1.814(6)
P1 C27 1.822(6)
O1 C1 1.254(6)
O2 C7 1.432(7)
O3 N7 1.225(5)
N1 C18 1.343(6)
N1 N2 1.345(6)
N2 C16 1.348(7)
N2 B1 1.536(8)
N3 C21 1.320(7)
N3 N4 1.349(6)
N4 C19 1.332(7)
N4 B1 1.568(9)
N5 C24 1.323(6)
N5 N6 1.368(6)
N6 C22 1.330(7)
N6 B1 1.532(9)
C1 C2 1.430(8)
C1 C6 1.520(7)
C2 C3 1.434(8)
C3 C4 1.529(7)
C4 C5 1.531(7)
C4 C9 1.550(7)
C5 C6 1.513(7)
C6 C7 1.564(7)
C7 C8 1.508(8)
C8 C9 1.511(8)
C10 C15 1.363(9)
C10 C11 1.388(8)
C11 C12 1.390(9)
C12 C13 1.354(10)
C13 C14 1.392(10)
C14 C15 1.379(9)
C16 C17 1.361(9)
C17 C18 1.390(8)
C19 C20 1.337(9)
C20 C21 1.387(8)
C22 C23 1.353(8)
C23 C24 1.364(7)
