#------------------------------------------------------------------------------
#$Date: 2016-03-21 08:01:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178590 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/01/4070178.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_4070178
loop_
_publ_author_name
'Harrison, Daniel P.'
'Zottig, Victor E.'
'Kosturko, George W.'
'Welch, Kevin D.'
'Sabat, Michal'
'Myers, William H.'
'Harman, W. Dean'
_publ_section_title
;
 Stereo- and Regioselective Nucleophilic Addition to Dihapto-Coordinated
 Pyridine Complexes
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              5682
_journal_paper_doi               10.1021/om900637x
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C20 H29 B N9 O4 P W'
_chemical_formula_weight         685.15
_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                 97.271(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7027(4)
_cell_length_b                   13.7471(5)
_cell_length_c                   15.9655(5)
_cell_measurement_reflns_used    9085
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.493
_cell_measurement_theta_min      2.296
_cell_volume                     2547.85(15)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33637
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    4.643
_exptl_absorpt_correction_T_max  0.8019
_exptl_absorpt_correction_T_min  0.5575
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.416
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         9188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0339P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0732
_reflns_number_gt                7427
_reflns_number_total             9188
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900637x_si_002.cif
_cod_data_source_block           C20H39BN9O4PW
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4070178
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
W W 0.170612(9) 0.254797(6) 0.192776(6) 0.02925(4) Uani 1 1 d
P1 P 0.27387(7) 0.13325(6) 0.29242(5) 0.04060(17) Uani 1 1 d
O1 O -0.2864(2) 0.07869(19) -0.04186(17) 0.0702(7) Uani 1 1 d
O2 O -0.2739(3) 0.23071(19) -0.0650(2) 0.0769(9) Uani 1 1 d
O3 O -0.2287(2) 0.33223(16) 0.11431(15) 0.0600(6) Uani 1 1 d
O4 O -0.0095(2) 0.2861(2) 0.30667(15) 0.0640(7) Uani 1 1 d
N1 N -0.12783(19) 0.19121(15) 0.12820(13) 0.0335(4) Uani 1 1 d
N2 N -0.2307(2) 0.15337(19) -0.04361(14) 0.0444(6) Uani 1 1 d
N3 N 0.1497(2) 0.39642(16) 0.12734(14) 0.0356(5) Uani 1 1 d
N4 N 0.2434(2) 0.44990(16) 0.11269(14) 0.0388(5) Uani 1 1 d
N5 N 0.28203(19) 0.35662(16) 0.27476(13) 0.0345(5) Uani 1 1 d
N6 N 0.3647(2) 0.41073(16) 0.24514(14) 0.0390(5) Uani 1 1 d
N7 N 0.3224(2) 0.24083(15) 0.11942(17) 0.0372(5) Uani 1 1 d
N8 N 0.3934(2) 0.31860(17) 0.11331(14) 0.0380(5) Uani 1 1 d
N9 N 0.0608(2) 0.27139(16) 0.25767(15) 0.0364(5) Uani 1 1 d
C2 C -0.0959(3) 0.1032(2) 0.17077(18) 0.0394(6) Uani 1 1 d
C3 C 0.0092(3) 0.0663(2) 0.17078(19) 0.0400(6) Uani 1 1 d
C4 C 0.1000(2) 0.11660(19) 0.13113(17) 0.0356(6) Uani 1 1 d
C5 C 0.0641(2) 0.20094(19) 0.07989(16) 0.0340(5) Uani 1 1 d
C6 C -0.0643(2) 0.2150(2) 0.05754(16) 0.0335(5) Uani 1 1 d
C7 C -0.1037(3) 0.1482(2) -0.01797(18) 0.0404(6) Uani 1 1 d
C8 C 0.2073(3) 0.5393(2) 0.0870(2) 0.0486(8) Uani 1 1 d
C9 C 0.0919(4) 0.5443(2) 0.0847(2) 0.0555(9) Uani 1 1 d
C10 C 0.0585(3) 0.4535(2) 0.11000(19) 0.0444(7) Uani 1 1 d
C11 C 0.4128(3) 0.4690(2) 0.3077(2) 0.0491(7) Uani 1 1 d
C12 C 0.3616(3) 0.4530(2) 0.3778(2) 0.0512(8) Uani 1 1 d
C13 C 0.2793(3) 0.3825(2) 0.35512(19) 0.0421(6) Uani 1 1 d
C14 C 0.4814(3) 0.2925(3) 0.0722(2) 0.0471(7) Uani 1 1 d
C15 C 0.4685(3) 0.1966(3) 0.0498(2) 0.0491(8) Uani 1 1 d
C16 C 0.3687(3) 0.1674(2) 0.07988(19) 0.0418(6) Uani 1 1 d
C17 C 0.4235(4) 0.1665(3) 0.3256(3) 0.0666(11) Uani 1 1 d
C18 C 0.2890(4) 0.0077(2) 0.2597(3) 0.0549(9) Uani 1 1 d
C19 C 0.2156(6) 0.1196(5) 0.3909(3) 0.0837(16) Uani 1 1 d
C22 C -0.2081(3) 0.25568(19) 0.1518(2) 0.0410(6) Uani 1 1 d
C23 C -0.2686(4) 0.2274(3) 0.2253(3) 0.0551(9) Uani 1 1 d
B1 B 0.3654(3) 0.4183(2) 0.1487(2) 0.0408(7) Uani 1 1 d
H1B H 0.432(2) 0.4701(19) 0.1332(16) 0.039(8) Uiso 1 1 d
H2 H -0.148(2) 0.078(2) 0.1950(17) 0.040(8) Uiso 1 1 d
H3 H 0.028(2) 0.000(2) 0.1977(16) 0.033(7) Uiso 1 1 d
H4 H 0.154(2) 0.072(2) 0.1176(16) 0.034(7) Uiso 1 1 d
H5 H 0.106(2) 0.210(2) 0.0334(18) 0.038(8) Uiso 1 1 d
H6 H -0.083(2) 0.2731(19) 0.0425(17) 0.024(7) Uiso 1 1 d
H7A H -0.094(2) 0.079(2) -0.0060(18) 0.052(9) Uiso 1 1 d
H7B H -0.067(2) 0.174(2) -0.0657(17) 0.037(7) Uiso 1 1 d
H8 H 0.257(3) 0.580(3) 0.076(2) 0.060(11) Uiso 1 1 d
H9 H 0.050(3) 0.588(3) 0.075(2) 0.071(12) Uiso 1 1 d
H10 H -0.011(3) 0.431(2) 0.1164(19) 0.050(10) Uiso 1 1 d
H11 H 0.472(2) 0.513(2) 0.2970(17) 0.039(8) Uiso 1 1 d
H12 H 0.368(3) 0.479(2) 0.420(2) 0.054(10) Uiso 1 1 d
H13 H 0.226(3) 0.354(2) 0.3861(18) 0.043(9) Uiso 1 1 d
H14 H 0.534(2) 0.340(2) 0.0668(18) 0.041(8) Uiso 1 1 d
H15 H 0.510(3) 0.166(2) 0.022(2) 0.055(10) Uiso 1 1 d
H16 H 0.330(2) 0.107(2) 0.0763(17) 0.045(8) Uiso 1 1 d
H17A H 0.427(4) 0.223(3) 0.351(3) 0.072(13) Uiso 1 1 d
H17B H 0.464(4) 0.123(4) 0.361(3) 0.112(17) Uiso 1 1 d
H17C H 0.457(4) 0.175(4) 0.271(3) 0.118(19) Uiso 1 1 d
H18A H 0.215(3) -0.022(3) 0.253(2) 0.067(11) Uiso 1 1 d
H18B H 0.326(3) -0.001(3) 0.211(2) 0.067(12) Uiso 1 1 d
H18C H 0.337(3) -0.030(3) 0.299(2) 0.072(12) Uiso 1 1 d
H19A H 0.141(3) 0.105(3) 0.373(2) 0.064(14) Uiso 1 1 d
H19B H 0.200(4) 0.175(4) 0.418(3) 0.096(17) Uiso 1 1 d
H19C H 0.242(4) 0.063(3) 0.419(3) 0.096(14) Uiso 1 1 d
H23A H -0.314(3) 0.173(3) 0.216(2) 0.055(10) Uiso 1 1 d
H23B H -0.321(4) 0.275(3) 0.234(3) 0.092(15) Uiso 1 1 d
H23C H -0.214(4) 0.216(3) 0.273(3) 0.089(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 C5 98.42(10)
N9 W N3 96.81(10)
C5 W N3 83.75(9)
N9 W N5 89.39(9)
C5 W N5 158.32(9)
N3 W N5 75.23(8)
N9 W C4 96.41(10)
C5 W C4 38.14(10)
N3 W C4 121.68(10)
N5 W C4 161.02(10)
N9 W N7 174.54(9)
C5 W N7 86.98(10)
N3 W N7 82.93(8)
N5 W N7 85.27(8)
C4 W N7 88.33(9)
N9 W P1 92.40(8)
C5 W P1 118.40(7)
N3 W P1 154.51(6)
N5 W P1 81.17(6)
C4 W P1 80.54(7)
N7 W P1 85.69(7)
C19 P1 C18 102.3(3)
C19 P1 C17 103.2(3)
C18 P1 C17 101.3(2)
C19 P1 W 114.69(18)
C18 P1 W 120.44(14)
C17 P1 W 112.65(16)
C22 N1 C2 124.5(2)
C22 N1 C6 119.8(2)
C2 N1 C6 115.6(2)
O2 N2 O1 122.8(3)
O2 N2 C7 119.1(3)
O1 N2 C7 118.1(3)
C10 N3 N4 106.8(2)
C10 N3 W 131.2(2)
N4 N3 W 120.84(17)
C8 N4 N3 108.4(3)
C8 N4 B1 127.9(3)
N3 N4 B1 120.9(2)
C13 N5 N6 107.1(2)
C13 N5 W 130.5(2)
N6 N5 W 122.20(16)
C11 N6 N5 108.5(2)
C11 N6 B1 130.2(3)
N5 N6 B1 118.7(2)
C16 N7 N8 105.7(2)
C16 N7 W 134.42(19)
N8 N7 W 119.77(16)
C14 N8 N7 109.7(2)
C14 N8 B1 129.3(3)
N7 N8 B1 120.9(2)
O4 N9 W 175.4(2)
C3 C2 N1 121.0(3)
C2 C3 C4 122.4(3)
C5 C4 C3 116.4(2)
C5 C4 W 68.62(14)
C3 C4 W 116.93(19)
C4 C5 C6 116.3(2)
C4 C5 W 73.25(15)
C6 C5 W 126.64(18)
N1 C6 C5 112.1(2)
N1 C6 C7 109.9(2)
C5 C6 C7 107.4(2)
N2 C7 C6 112.0(2)
N4 C8 C9 109.2(3)
C8 C9 C10 105.3(3)
N3 C10 C9 110.2(3)
N6 C11 C12 109.3(3)
C11 C12 C13 105.3(3)
N5 C13 C12 109.8(3)
N8 C14 C15 108.7(3)
C14 C15 C16 105.0(3)
N7 C16 C15 110.8(3)
O3 C22 N1 121.3(3)
O3 C22 C23 121.7(3)
N1 C22 C23 117.0(3)
N4 B1 N8 110.3(2)
N4 B1 N6 105.7(2)
N8 B1 N6 109.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
W N9 1.764(2)
W C5 2.186(3)
W N3 2.208(2)
W N5 2.223(2)
W C4 2.248(3)
W N7 2.257(2)
W P1 2.5093(7)
P1 C19 1.802(4)
P1 C18 1.819(4)
P1 C17 1.823(4)
O1 N2 1.218(3)
O2 N2 1.208(3)
O3 C22 1.220(3)
O4 N9 1.222(3)
N1 C22 1.378(4)
N1 C2 1.414(3)
N1 C6 1.464(3)
N2 C7 1.493(4)
N3 C10 1.325(4)
N3 N4 1.365(3)
N4 C8 1.346(4)
N4 B1 1.533(4)
N5 C13 1.336(3)
N5 N6 1.353(3)
N6 C11 1.346(3)
N6 B1 1.545(4)
N7 C16 1.341(3)
N7 N8 1.365(3)
N8 C14 1.338(4)
N8 B1 1.533(4)
C2 C3 1.331(4)
C3 C4 1.476(4)
C4 C5 1.450(4)
C5 C6 1.513(4)
C6 C7 1.539(4)
C8 C9 1.349(5)
C9 C10 1.383(4)
C11 C12 1.353(5)
C12 C13 1.381(4)
C14 C15 1.369(5)
C15 C16 1.378(4)
C22 C23 1.496(5)
