#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:04:36 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178834 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/88/4108850.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_4108850
loop_
_publ_author_name
'Daniel P. Harrison'
'Kevin D. Welch'
'Adam C. Nichols-Nielander'
'Michal Sabat'
'William H. Myers'
'W. Dean Harman'
_publ_section_title
;
 Efficient Synthesis of an η2-Pyridine Complex and a Preliminary
 Investigation of the Bound Heterocycle's Reactivity
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16844
_journal_page_last               16845
_journal_paper_doi               10.1021/ja807521d
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C22 H30 B N8 O3 P W'
_chemical_formula_weight         680.17
_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                 97.642(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2881(1)
_cell_length_b                   14.0590(1)
_cell_length_c                   18.7375(2)
_cell_measurement_reflns_used    6419
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.04
_cell_volume                     2686.13(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11943
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    4.39
_exptl_absorpt_correction_T_max  0.4068
_exptl_absorpt_correction_T_min  0.3516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.321
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    allref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         6174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0187
_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)+(0.0168P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0358
_refine_ls_wR_factor_ref         0.0378
_reflns_number_gt                5150
_reflns_number_total             6174
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja807521d_si_005.cif
_cod_data_source_block           C22H30BN8O3PW
_cod_database_code               4108850
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
W1 W 0.843728(8) 0.784710(6) 0.824010(4) 0.01328(3) Uani 1 1 d
P1 P 0.60196(5) 0.78394(4) 0.77977(3) 0.01948(13) Uani 1 1 d
O1 O 1.23047(15) 0.73189(11) 0.69114(9) 0.0295(4) Uani 1 1 d
O2 O 1.26343(16) 0.97143(13) 0.83512(9) 0.0374(4) Uani 1 1 d
O3 O 0.88970(16) 0.62338(11) 0.72550(8) 0.0308(4) Uani 1 1 d
N1 N 1.03703(16) 0.80926(12) 0.67517(9) 0.0148(4) Uani 1 1 d
N2 N 0.78589(18) 0.68630(13) 0.90710(9) 0.0189(4) Uani 1 1 d
N3 N 0.81493(18) 0.70582(13) 0.97905(9) 0.0195(4) Uani 1 1 d
N4 N 0.80735(17) 0.89591(13) 0.90476(9) 0.0181(4) Uani 1 1 d
N5 N 0.85029(17) 0.88215(13) 0.97648(9) 0.0197(4) Uani 1 1 d
N6 N 1.02825(17) 0.75791(13) 0.89601(9) 0.0170(4) Uani 1 1 d
N7 N 1.03547(18) 0.76760(13) 0.96907(9) 0.0194(4) Uani 1 1 d
N8 N 0.87155(17) 0.69108(13) 0.76471(10) 0.0177(4) Uani 1 1 d
C2 C 1.0788(2) 0.86944(15) 0.73850(11) 0.0165(5) Uani 1 1 d
C3 C 0.9654(2) 0.89192(15) 0.78036(11) 0.0151(5) Uani 1 1 d
C4 C 0.8357(2) 0.90204(16) 0.74094(11) 0.0166(5) Uani 1 1 d
C5 C 0.8199(2) 0.87237(16) 0.66541(11) 0.0176(5) Uani 1 1 d
C6 C 0.9129(2) 0.82747(16) 0.63586(12) 0.0180(5) Uani 1 1 d
C7 C 1.1206(2) 0.74061(17) 0.65757(12) 0.0205(5) Uani 1 1 d
C8 C 1.0725(3) 0.6760(2) 0.59566(14) 0.0278(6) Uani 1 1 d
C9 C 1.1453(2) 0.95938(15) 0.71767(11) 0.0190(5) Uani 1 1 d
C10 C 1.1292(3) 1.0004(2) 0.65356(14) 0.0301(6) Uani 1 1 d
C11 C 1.2379(2) 1.00350(18) 0.77537(14) 0.0295(6) Uani 1 1 d
C12 C 0.7752(2) 0.63281(19) 1.01692(13) 0.0290(6) Uani 1 1 d
C13 C 0.7185(3) 0.5653(2) 0.97063(13) 0.0329(6) Uani 1 1 d
C14 C 0.7284(2) 0.60052(17) 0.90255(13) 0.0259(6) Uani 1 1 d
C15 C 0.8222(2) 0.95927(18) 1.01355(13) 0.0267(6) Uani 1 1 d
C16 C 0.7599(3) 1.02411(19) 0.96726(14) 0.0317(6) Uani 1 1 d
C17 C 0.7528(2) 0.98287(17) 0.89982(13) 0.0251(5) Uani 1 1 d
C18 C 1.1537(2) 0.73786(17) 1.00008(13) 0.0236(5) Uani 1 1 d
C19 C 1.2252(2) 0.70938(18) 0.94769(13) 0.0266(6) Uani 1 1 d
C20 C 1.1435(2) 0.72200(16) 0.88326(13) 0.0212(5) Uani 1 1 d
C21 C 0.4967(3) 0.7740(2) 0.85025(16) 0.0349(7) Uani 1 1 d
C22 C 0.5558(3) 0.6820(2) 0.72189(15) 0.0299(6) Uani 1 1 d
C23 C 0.5205(3) 0.8815(2) 0.72779(16) 0.0319(6) Uani 1 1 d
B1 B 0.9106(3) 0.78771(19) 1.00368(14) 0.0208(6) Uani 1 1 d
H1B H 0.933(2) 0.7914(13) 1.0609(11) 0.013(5) Uiso 1 1 d
H2 H 1.1439(19) 0.8346(15) 0.7661(10) 0.010(5) Uiso 1 1 d
H3 H 0.9870(17) 0.9376(14) 0.8145(9) 0.005(5) Uiso 1 1 d
H4 H 0.7846(19) 0.9519(14) 0.7533(9) 0.012(5) Uiso 1 1 d
H5 H 0.744(2) 0.8871(15) 0.6361(11) 0.023(6) Uiso 1 1 d
H6 H 0.9066(19) 0.8065(14) 0.5892(11) 0.012(6) Uiso 1 1 d
H8A H 0.984(3) 0.6517(19) 0.6001(13) 0.051(8) Uiso 1 1 d
H8B H 1.065(2) 0.7115(16) 0.5514(14) 0.033(7) Uiso 1 1 d
H8C H 1.127(2) 0.6289(19) 0.5953(13) 0.044(8) Uiso 1 1 d
H10A H 1.070(2) 0.9756(18) 0.6153(12) 0.036(7) Uiso 1 1 d
H10B H 1.172(2) 1.0587(18) 0.6462(12) 0.033(7) Uiso 1 1 d
H11 H 1.283(2) 1.0631(17) 0.7605(11) 0.029(6) Uiso 1 1 d
H12 H 0.791(2) 0.6315(17) 1.0622(12) 0.029(7) Uiso 1 1 d
H13 H 0.684(2) 0.5087(17) 0.9794(11) 0.030(7) Uiso 1 1 d
H14 H 0.700(2) 0.5733(16) 0.8591(11) 0.029(7) Uiso 1 1 d
H15 H 0.8427(19) 0.9616(15) 1.0581(11) 0.015(6) Uiso 1 1 d
H16 H 0.728(2) 1.0817(19) 0.9783(12) 0.041(8) Uiso 1 1 d
H17 H 0.716(2) 1.0078(16) 0.8543(11) 0.022(6) Uiso 1 1 d
H18 H 1.174(2) 0.7392(16) 1.0476(13) 0.024(6) Uiso 1 1 d
H19 H 1.307(2) 0.6853(16) 0.9533(12) 0.031(7) Uiso 1 1 d
H20 H 1.155(2) 0.7068(14) 0.8365(12) 0.020(6) Uiso 1 1 d
H21A H 0.513(3) 0.7184(18) 0.8782(15) 0.043(9) Uiso 1 1 d
H21B H 0.404(3) 0.7722(19) 0.8284(15) 0.057(9) Uiso 1 1 d
H21C H 0.509(3) 0.834(2) 0.8762(14) 0.047(9) Uiso 1 1 d
H22A H 0.611(2) 0.6802(18) 0.6841(13) 0.035(7) Uiso 1 1 d
H22B H 0.580(2) 0.6239(19) 0.7486(12) 0.040(8) Uiso 1 1 d
H22C H 0.470(3) 0.6820(19) 0.7057(14) 0.046(8) Uiso 1 1 d
H23A H 0.556(2) 0.8861(18) 0.6851(13) 0.039(8) Uiso 1 1 d
H23B H 0.533(2) 0.9397(19) 0.7533(13) 0.045(8) Uiso 1 1 d
H23C H 0.424(2) 0.8708(17) 0.7192(11) 0.035(7) 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
N8 W1 C3 97.44(8)
N8 W1 N6 93.38(7)
C3 W1 N6 81.84(7)
N8 W1 N2 93.30(8)
C3 W1 N2 155.69(7)
N6 W1 N2 75.79(6)
N8 W1 N4 176.17(7)
C3 W1 N4 85.81(7)
N6 W1 N4 85.06(6)
N2 W1 N4 82.94(7)
N8 W1 C4 96.00(8)
C3 W1 C4 37.83(7)
N6 W1 C4 119.62(7)
N2 W1 C4 161.33(7)
N4 W1 C4 87.81(7)
N8 W1 P1 91.45(6)
C3 W1 P1 118.03(6)
N6 W1 P1 158.74(5)
N2 W1 P1 83.28(5)
N4 W1 P1 88.79(5)
C4 W1 P1 80.34(6)
C22 P1 C21 103.81(15)
C22 P1 C23 102.08(14)
C21 P1 C23 99.79(14)
C22 P1 W1 111.55(9)
C21 P1 W1 114.74(10)
C23 P1 W1 122.53(9)
C7 N1 C6 124.00(18)
C7 N1 C2 118.42(17)
C6 N1 C2 117.57(17)
C14 N2 N3 106.23(18)
C14 N2 W1 132.25(15)
N3 N2 W1 121.42(13)
C12 N3 N2 108.98(18)
C12 N3 B1 129.72(19)
N2 N3 B1 119.36(17)
C17 N4 N5 105.84(17)
C17 N4 W1 133.95(14)
N5 N4 W1 120.15(13)
C15 N5 N4 109.29(19)
C15 N5 B1 129.64(19)
N4 N5 B1 120.94(17)
C20 N6 N7 106.54(17)
C20 N6 W1 131.63(15)
N7 N6 W1 121.45(13)
C18 N7 N6 109.11(18)
C18 N7 B1 129.28(19)
N6 N7 B1 120.16(17)
O3 N8 W1 177.43(16)
N1 C2 C9 111.42(17)
N1 C2 C3 111.87(17)
C9 C2 C3 111.28(17)
C4 C3 C2 118.44(18)
C4 C3 W1 73.93(12)
C2 C3 W1 124.43(15)
C3 C4 C5 116.27(19)
C3 C4 W1 68.24(12)
C5 C4 W1 116.53(15)
C6 C5 C4 123.1(2)
C5 C6 N1 121.4(2)
O1 C7 N1 121.1(2)
O1 C7 C8 121.5(2)
N1 C7 C8 117.5(2)
C10 C9 C11 118.1(2)
C10 C9 C2 126.3(2)
C11 C9 C2 115.55(19)
O2 C11 C9 124.2(2)
N3 C12 C13 109.3(2)
C12 C13 C14 105.0(2)
N2 C14 C13 110.4(2)
N5 C15 C16 109.1(2)
C15 C16 C17 105.4(2)
N4 C17 C16 110.3(2)
N7 C18 C19 108.9(2)
C18 C19 C20 105.5(2)
N6 C20 C19 110.0(2)
N5 B1 N7 110.15(19)
N5 B1 N3 109.52(19)
N7 B1 N3 105.75(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
W1 N8 1.7703(18)
W1 C3 2.186(2)
W1 N6 2.2102(17)
W1 N2 2.2222(18)
W1 N4 2.2414(17)
W1 C4 2.262(2)
W1 P1 2.5151(6)
P1 C22 1.822(3)
P1 C21 1.821(3)
P1 C23 1.820(3)
O1 C7 1.225(3)
O2 C11 1.203(3)
O3 N8 1.232(2)
N1 C7 1.362(3)
N1 C6 1.410(3)
N1 C2 1.474(3)
N2 C14 1.341(3)
N2 N3 1.369(2)
N3 C12 1.342(3)
N3 B1 1.545(3)
N4 C17 1.343(3)
N4 N5 1.371(2)
N5 C15 1.340(3)
N5 B1 1.524(3)
N6 C20 1.339(3)
N6 N7 1.368(2)
N7 C18 1.343(3)
N7 B1 1.540(3)
C2 C9 1.513(3)
C2 C3 1.523(3)
C3 C4 1.444(3)
C4 C5 1.464(3)
C5 C6 1.327(3)
C7 C8 1.504(3)
C9 C10 1.323(3)
C9 C11 1.479(3)
C12 C13 1.363(3)
C13 C14 1.385(3)
C15 C16 1.359(3)
C16 C17 1.383(3)
C18 C19 1.362(3)
C19 C20 1.388(3)
