#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:12:15 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178889 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/18/4111843.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_4111843
loop_
_publ_author_name
'Peter M. Graham'
'David A. Delafuente'
'Weijun Liu'
'William H. Myers'
'Michal Sabat'
'W. D. Harman'
_publ_section_title
;
 Facile Diels-Alder Reactions with Pyridines Promoted by Tungsten
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10568
_journal_page_last               10572
_journal_paper_doi               10.1021/ja050143r
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C22 H35 B N9 O2 P W'
_chemical_formula_weight         683.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.1390(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2142(6)
_cell_length_b                   11.3561(7)
_cell_length_c                   23.3692(15)
_cell_measurement_reflns_used    7036
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      32.468
_cell_measurement_theta_min      2.222
_cell_volume                     2706.6(3)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            36907
_diffrn_reflns_theta_full        32.58
_diffrn_reflns_theta_max         32.58
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    4.365
_exptl_absorpt_correction_T_max  0.801927
_exptl_absorpt_correction_T_min  0.631984
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS '
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         3.409
_refine_diff_density_min         -1.606
_refine_diff_density_rms         0.182
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    allref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         9826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0406
_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)+(0.0458P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                7581
_reflns_number_total             9826
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja050143rsi20050110_110420.cif
_cod_data_source_block           c22h35bn9o2pw
_cod_database_code               4111843
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
W W 0.458607(13) 0.857290(12) 0.851309(6) 0.01564(4) Uani 1 1 d .
P P 0.47902(11) 0.69330(9) 0.92259(5) 0.0240(2) Uani 1 1 d .
O1 O 0.1711(3) 0.8145(3) 0.83144(14) 0.0306(7) Uani 1 1 d .
O2 O 0.6568(9) 0.8911(9) 0.5552(3) 0.200(5) Uani 1 1 d .
N1 N 0.2289(3) 1.1054(3) 0.90140(16) 0.0264(7) Uani 1 1 d .
N2 N 0.3545(4) 1.2104(3) 0.84081(17) 0.0309(8) Uani 1 1 d .
N3 N 0.4875(3) 0.7114(3) 0.79215(14) 0.0188(6) Uani 1 1 d .
N4 N 0.5919(3) 0.7012(3) 0.75940(14) 0.0207(6) Uani 1 1 d .
N5 N 0.4972(3) 0.9492(3) 0.77046(14) 0.0200(6) Uani 1 1 d .
N6 N 0.5975(3) 0.9138(3) 0.73821(14) 0.0221(6) Uani 1 1 d .
N7 N 0.6778(3) 0.8642(3) 0.86090(14) 0.0202(6) Uani 1 1 d .
N8 N 0.7492(3) 0.8319(3) 0.81561(15) 0.0204(6) Uani 1 1 d .
N9 N 0.2879(3) 0.8370(3) 0.84029(15) 0.0194(6) Uani 1 1 d .
C1 C 0.4822(6) 1.2537(4) 0.8261(3) 0.0384(11) Uani 1 1 d .
C2 C 0.3424(4) 1.1172(3) 0.87778(18) 0.0228(8) Uani 1 1 d .
C3 C 0.4535(4) 1.0388(3) 0.88871(17) 0.0202(7) Uani 1 1 d .
C4 C 0.4449(4) 0.9528(3) 0.93411(17) 0.0220(8) Uani 1 1 d .
C5 C 0.3194(4) 0.9471(4) 0.96074(18) 0.0241(8) Uani 1 1 d .
C6 C 0.2218(4) 1.0176(4) 0.94233(18) 0.0254(8) Uani 1 1 d .
C7 C 0.2486(6) 1.2962(4) 0.8349(3) 0.0415(12) Uani 1 1 d .
C8 C 0.5755(5) 0.6064(4) 0.7252(2) 0.0306(9) Uani 1 1 d .
C9 C 0.4590(4) 0.5531(4) 0.73570(19) 0.0291(9) Uani 1 1 d .
C10 C 0.4075(4) 0.6212(3) 0.77771(19) 0.0228(8) Uani 1 1 d .
C11 C 0.5915(4) 0.9742(4) 0.68863(19) 0.0286(9) Uani 1 1 d .
C12 C 0.4876(4) 1.0507(4) 0.6886(2) 0.0298(9) Uani 1 1 d .
C13 C 0.4315(4) 1.0317(4) 0.74001(18) 0.0243(8) Uani 1 1 d .
C14 C 0.8765(4) 0.8319(3) 0.8320(2) 0.0254(9) Uani 1 1 d .
C15 C 0.8908(4) 0.8663(4) 0.8879(2) 0.0344(10) Uani 1 1 d .
C16 C 0.7641(4) 0.8853(4) 0.9044(2) 0.0287(9) Uani 1 1 d .
C17 C 0.5393(5) 0.7196(5) 0.9963(2) 0.0364(11) Uani 1 1 d .
C18 C 0.5924(6) 0.5779(5) 0.9031(2) 0.0390(12) Uani 1 1 d .
C19 C 0.3250(5) 0.6174(5) 0.9318(3) 0.0382(12) Uani 1 1 d .
C20 C 0.5775(10) 0.8139(9) 0.5506(3) 0.094(3) Uani 1 1 d .
C21 C 0.4393(11) 0.8383(10) 0.5205(5) 0.133(4) Uani 1 1 d .
H21A H 0.4270 0.7885 0.4874 0.199 Uiso 1 1 calc R
H21B H 0.4339 0.9193 0.5088 0.199 Uiso 1 1 calc R
H21C H 0.3725 0.8220 0.5467 0.199 Uiso 1 1 calc R
C22 C 0.5930(10) 0.6990(8) 0.5735(4) 0.103(3) Uani 1 1 d .
H22A H 0.6792 0.6912 0.5916 0.154 Uiso 1 1 calc R
H22B H 0.5817 0.6423 0.5432 0.154 Uiso 1 1 calc R
H22C H 0.5286 0.6857 0.6012 0.154 Uiso 1 1 calc R
B B 0.6851(4) 0.8084(4) 0.7562(2) 0.0222(8) Uani 1 1 d .
H1A H 0.526(8) 1.286(7) 0.858(3) 0.10(3) Uiso 1 1 d .
H1B1 H 0.757(4) 0.791(4) 0.7250(17) 0.021(11) Uiso 1 1 d .
H1B H 0.539(5) 1.180(5) 0.813(2) 0.038(14) Uiso 1 1 d .
H1C H 0.467(4) 1.297(4) 0.7999(17) 0.005(9) Uiso 1 1 d .
H3 H 0.535(4) 1.082(4) 0.8814(19) 0.028(12) Uiso 1 1 d .
H4 H 0.516(4) 0.942(4) 0.9598(17) 0.015(10) Uiso 1 1 d .
H5 H 0.305(4) 0.897(4) 0.9868(18) 0.014(10) Uiso 1 1 d .
H6 H 0.138(5) 1.021(4) 0.958(2) 0.033(13) Uiso 1 1 d .
H7A H 0.266(5) 1.332(5) 0.800(2) 0.040(15) Uiso 1 1 d .
H7B H 0.166(5) 1.254(4) 0.833(2) 0.031(13) Uiso 1 1 d .
H7C H 0.248(6) 1.342(5) 0.868(3) 0.049(17) Uiso 1 1 d .
H8 H 0.637(5) 0.594(4) 0.701(2) 0.032(13) Uiso 1 1 d .
H9 H 0.422(4) 0.483(4) 0.7201(17) 0.017(10) Uiso 1 1 d .
H10 H 0.331(5) 0.615(4) 0.7989(19) 0.023(12) Uiso 1 1 d .
H11 H 0.647(5) 0.956(4) 0.661(2) 0.032(13) Uiso 1 1 d .
H12 H 0.467(5) 1.101(4) 0.660(2) 0.030(13) Uiso 1 1 d .
H13 H 0.361(4) 1.068(4) 0.7556(18) 0.023(11) Uiso 1 1 d .
H14 H 0.931(5) 0.812(4) 0.809(2) 0.028(13) Uiso 1 1 d .
H15 H 0.957(5) 0.875(4) 0.909(2) 0.025(13) Uiso 1 1 d .
H16 H 0.742(5) 0.900(4) 0.937(2) 0.032(14) Uiso 1 1 d .
H17A H 0.637(5) 0.759(5) 0.997(2) 0.044(15) Uiso 1 1 d .
H17B H 0.492(6) 0.761(5) 1.020(2) 0.051(17) Uiso 1 1 d .
H17C H 0.540(5) 0.642(4) 1.015(2) 0.028(13) Uiso 1 1 d .
H18A H 0.673(8) 0.597(7) 0.902(3) 0.09(3) Uiso 1 1 d .
H18B H 0.602(5) 0.519(5) 0.931(2) 0.044(15) Uiso 1 1 d .
H18C H 0.558(6) 0.541(5) 0.868(3) 0.063(19) Uiso 1 1 d .
H19A H 0.273(7) 0.669(6) 0.941(3) 0.07(2) Uiso 1 1 d .
H19B H 0.338(5) 0.553(5) 0.961(2) 0.055(17) Uiso 1 1 d .
H19C H 0.297(5) 0.577(5) 0.899(2) 0.041(15) 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'
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
N9 W N3 88.58(13)
N9 W N5 99.09(13)
N3 W N5 77.38(11)
N9 W C4 94.68(15)
N3 W C4 159.04(14)
N5 W C4 122.28(13)
N9 W N7 173.87(13)
N3 W N7 85.48(11)
N5 W N7 81.08(12)
C4 W N7 90.35(13)
N9 W C3 97.67(13)
N3 W C3 161.78(13)
N5 W C3 84.71(13)
C4 W C3 37.81(14)
N7 W C3 88.45(12)
N9 W P 92.62(10)
N3 W P 81.23(9)
N5 W P 155.26(8)
C4 W P 77.94(11)
N7 W P 85.01(9)
C3 W P 115.36(11)
C19 P C17 102.5(3)
C19 P C18 104.7(3)
C17 P C18 99.7(3)
C19 P W 113.04(18)
C17 P W 121.29(18)
C18 P W 113.55(19)
C2 N1 C6 116.3(3)
C2 N2 C1 121.4(4)
C2 N2 C7 118.8(4)
C1 N2 C7 115.0(4)
C10 N3 N4 106.3(3)
C10 N3 W 129.5(3)
N4 N3 W 124.1(2)
C8 N4 N3 109.2(3)
C8 N4 B 131.0(4)
N3 N4 B 117.8(3)
C13 N5 N6 106.5(3)
C13 N5 W 132.7(3)
N6 N5 W 120.4(2)
C11 N6 N5 109.0(3)
C11 N6 B 129.1(3)
N5 N6 B 121.4(3)
C16 N7 N8 106.3(3)
C16 N7 W 134.4(3)
N8 N7 W 119.1(2)
C14 N8 N7 109.2(3)
C14 N8 B 128.6(4)
N7 N8 B 122.0(3)
O1 N9 W 175.2(3)
N1 C2 N2 116.9(4)
N1 C2 C3 124.1(4)
N2 C2 C3 119.0(4)
C4 C3 C2 117.6(3)
C4 C3 W 70.7(2)
C2 C3 W 121.9(3)
C3 C4 C5 115.7(4)
C3 C4 W 71.5(2)
C5 C4 W 116.6(3)
C6 C5 C4 119.8(4)
C5 C6 N1 126.1(4)
N4 C8 C9 109.2(4)
C8 C9 C10 104.4(4)
N3 C10 C9 110.9(4)
N6 C11 C12 108.8(4)
C11 C12 C13 105.0(4)
N5 C13 C12 110.7(4)
N8 C14 C15 109.1(4)
C14 C15 C16 104.9(4)
N7 C16 C15 110.5(4)
O2 C20 C22 125.5(13)
O2 C20 C21 120.0(12)
C22 C20 C21 114.4(8)
N8 B N6 109.0(3)
N8 B N4 109.2(3)
N6 B N4 105.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
W N9 1.764(3)
W N3 2.188(3)
W N5 2.213(3)
W C4 2.229(4)
W N7 2.239(3)
W C3 2.241(4)
W P 2.4996(11)
P C19 1.817(5)
P C17 1.821(5)
P C18 1.823(5)
O1 N9 1.227(4)
O2 C20 1.194(9)
N1 C2 1.318(5)
N1 C6 1.386(6)
N2 C2 1.376(5)
N2 C1 1.452(6)
N2 C7 1.457(6)
N3 C10 1.342(5)
N3 N4 1.351(4)
N4 C8 1.345(5)
N4 B 1.550(6)
N5 C13 1.335(5)
N5 N6 1.365(4)
N6 C11 1.345(5)
N6 B 1.539(6)
N7 C16 1.330(5)
N7 N8 1.368(4)
N8 C14 1.336(5)
N8 B 1.526(6)
C2 C3 1.454(5)
C3 C4 1.448(6)
C4 C5 1.456(5)
C5 C6 1.332(6)
C8 C9 1.369(6)
C9 C10 1.376(6)
C11 C12 1.371(6)
C12 C13 1.377(6)
C14 C15 1.363(7)
C15 C16 1.387(6)
C20 C22 1.415(12)
C20 C21 1.567(14)
