#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:03:02 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178632 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/43/4074366.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_4074366
loop_
_publ_author_name
'Welch, Kevin D.'
'Smith, Philip L.'
'Keller, Andrew P.'
'Myers, William H.'
'Sabat, Michal'
'Harman, W. Dean'
_publ_section_title
;
 Osmium(II)-, Rhenium(I)-, and Tungsten(0)-Promoted Dipolar Cycloaddition
 Reactions with Pyrroles:  Exploiting the Azomethine Ylide
 Character of This Heterocycle
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              5067
_journal_paper_doi               10.1021/om060586j
_journal_volume                  25
_journal_year                    2006
_chemical_formula_sum            'C24 H36 B N8 O5 P W'
_chemical_formula_weight         742.24
_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                 95.7450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2690(10)
_cell_length_b                   16.1380(10)
_cell_length_c                   21.9880(10)
_cell_measurement_reflns_used    7246
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.010
_cell_measurement_theta_min      2.731
_cell_volume                     2919.5(4)
_computing_cell_refinement       '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 0.928
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'Bruker SMART APEX CCD 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     0.71074
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            20254
_diffrn_reflns_theta_full        32.52
_diffrn_reflns_theta_max         32.52
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    4.060
_exptl_absorpt_correction_T_max  0.821730
_exptl_absorpt_correction_T_min  0.660640
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         2.291
_refine_diff_density_min         -2.802
_refine_diff_density_rms         0.234
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         20254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0433
_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)+(0.0372P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                14122
_reflns_number_total             20254
_reflns_threshold_expression
'>2sigma(I) computing_data_collection Bruker SMART'
_cod_data_source_file            om060586jsi20060630_040706.cif
_cod_data_source_block           C24H36BN8O5PW
_cod_depositor_comments
;
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)/n
_cod_database_code               4074366
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
W W 0.837055(12) 0.161693(6) 0.791962(4) 0.01076(2) Uani 1 1 d
P P 0.59262(8) 0.25404(4) 0.79653(3) 0.01412(11) Uani 1 1 d
O1 O 1.1973(3) 0.11864(16) 0.54823(10) 0.0225(4) Uani 1 1 d
O2 O 0.9466(3) 0.11279(17) 0.49841(10) 0.0256(5) Uani 1 1 d
O3 O 0.9389(3) 0.35316(15) 0.58606(12) 0.0271(5) Uani 1 1 d
O4 O 0.6704(3) 0.34145(13) 0.59101(10) 0.0203(4) Uani 1 1 d
O5 O 0.6389(3) 0.00774(15) 0.76252(12) 0.0271(5) Uani 1 1 d
N1 N 0.7960(3) 0.09332(15) 0.63923(11) 0.0159(4) Uani 1 1 d
N2 N 0.7932(3) 0.14636(14) 0.88943(11) 0.0147(4) Uani 1 1 d
N3 N 0.8937(3) 0.17723(16) 0.93648(11) 0.0172(4) Uani 1 1 d
N4 N 1.0641(3) 0.10021(14) 0.83465(11) 0.0150(4) Uani 1 1 d
N5 N 1.1334(3) 0.12524(15) 0.89042(11) 0.0156(4) Uani 1 1 d
N6 N 0.9774(3) 0.27542(14) 0.82542(11) 0.0151(4) Uani 1 1 d
N7 N 1.0629(3) 0.27632(15) 0.88205(11) 0.0162(4) Uani 1 1 d
N8 N 0.7212(3) 0.07117(14) 0.77266(11) 0.0150(4) Uani 1 1 d
C1 C 0.8144(3) 0.21771(15) 0.70032(11) 0.0120(4) Uani 1 1 d
C2 C 0.9691(3) 0.17360(15) 0.71005(12) 0.0137(4) Uani 1 1 d
C3 C 0.9677(3) 0.11504(16) 0.65409(12) 0.0140(4) Uani 1 1 d
C4 C 0.9881(3) 0.17676(17) 0.59916(13) 0.0153(4) Uani 1 1 d
C5 C 0.8176(3) 0.21645(17) 0.58906(12) 0.0149(4) Uani 1 1 d
C6 C 0.7280(3) 0.17744(16) 0.64178(12) 0.0133(4) Uani 1 1 d
C7 C 1.0780(4) 0.04044(19) 0.65897(14) 0.0204(5) Uani 1 1 d
C8 C 0.5446(4) 0.17469(19) 0.63135(15) 0.0195(5) Uani 1 1 d
C9 C 1.0361(3) 0.13320(19) 0.54233(13) 0.0180(5) Uani 1 1 d
C10 C 0.8208(4) 0.31007(17) 0.58853(12) 0.0171(5) Uani 1 1 d
C11 C 1.2605(5) 0.0691(3) 0.50131(16) 0.0275(7) Uani 1 1 d
C12 C 0.6611(5) 0.4311(2) 0.59240(17) 0.0261(6) Uani 1 1 d
C13 C 0.8291(4) 0.1650(2) 0.98988(13) 0.0214(5) Uani 1 1 d
C14 C 0.6812(4) 0.1258(2) 0.97784(15) 0.0235(6) Uani 1 1 d
C15 C 0.6642(3) 0.11439(19) 0.91417(13) 0.0183(5) Uani 1 1 d
C16 C 1.2514(3) 0.0718(2) 0.91103(14) 0.0188(5) Uani 1 1 d
C17 C 1.2618(4) 0.01004(19) 0.86786(14) 0.0199(5) Uani 1 1 d
C18 C 1.1426(3) 0.03113(17) 0.82088(14) 0.0176(5) Uani 1 1 d
C19 C 1.1288(4) 0.35237(19) 0.89335(16) 0.0223(6) Uani 1 1 d
C20 C 1.0864(4) 0.4019(2) 0.84323(16) 0.0252(6) Uani 1 1 d
C21 C 0.9928(4) 0.35157(17) 0.80217(14) 0.0188(5) Uani 1 1 d
C22 C 0.5927(4) 0.3101(2) 0.86883(15) 0.0246(6) Uani 1 1 d
C23 C 0.3969(4) 0.2014(2) 0.78907(16) 0.0224(6) Uani 1 1 d
C24 C 0.5525(4) 0.34073(19) 0.74441(14) 0.0204(5) Uani 1 1 d
B B 1.0690(4) 0.2002(2) 0.92431(14) 0.0169(5) Uani 1 1 d
H1 H 0.814(4) 0.281(2) 0.7003(16) 0.011(8) Uiso 1 1 d
H1B H 1.149(5) 0.209(3) 0.9640(18) 0.017(9) Uiso 1 1 d
H1N H 0.767(6) 0.064(3) 0.669(2) 0.035(13) Uiso 1 1 d
H2 H 1.071(5) 0.204(3) 0.7192(18) 0.021(10) Uiso 1 1 d
H4 H 1.077(4) 0.217(2) 0.6107(15) 0.004(7) Uiso 1 1 d
H5 H 0.761(5) 0.197(3) 0.5494(19) 0.022(10) Uiso 1 1 d
H7A H 1.191(5) 0.057(3) 0.6729(19) 0.023(10) Uiso 1 1 d
H7B H 1.075(5) 0.012(3) 0.6217(19) 0.022(10) Uiso 1 1 d
H7C H 1.038(5) 0.005(3) 0.690(2) 0.028(11) Uiso 1 1 d
H8A H 0.504(4) 0.139(2) 0.6516(17) 0.009(8) Uiso 1 1 d
H8B H 0.482(5) 0.226(3) 0.639(2) 0.029(12) Uiso 1 1 d
H8C H 0.497(7) 0.147(3) 0.597(3) 0.047(15) Uiso 1 1 d
H11A H 1.189(8) 0.032(4) 0.485(3) 0.07(2) Uiso 1 1 d
H11B H 1.364(8) 0.045(4) 0.519(3) 0.07(2) Uiso 1 1 d
H11C H 1.291(8) 0.103(4) 0.471(3) 0.07(2) Uiso 1 1 d
H12A H 0.547(6) 0.441(3) 0.592(2) 0.036(13) Uiso 1 1 d
H12B H 0.716(5) 0.454(3) 0.630(2) 0.027(11) Uiso 1 1 d
H12C H 0.695(6) 0.455(3) 0.556(2) 0.033(12) Uiso 1 1 d
H13 H 0.881(6) 0.182(3) 1.026(2) 0.028(12) Uiso 1 1 d
H14 H 0.614(5) 0.108(3) 1.006(2) 0.029(12) Uiso 1 1 d
H15 H 0.573(5) 0.089(3) 0.8888(18) 0.020(10) Uiso 1 1 d
H16 H 1.306(5) 0.085(3) 0.9468(18) 0.018(9) Uiso 1 1 d
H17 H 1.332(5) -0.030(3) 0.870(2) 0.026(11) Uiso 1 1 d
H18 H 1.118(5) 0.008(3) 0.782(2) 0.030(12) Uiso 1 1 d
H19 H 1.196(6) 0.363(3) 0.929(2) 0.032(12) Uiso 1 1 d
H20 H 1.115(5) 0.456(3) 0.839(2) 0.027(11) Uiso 1 1 d
H21 H 0.947(5) 0.365(2) 0.7612(18) 0.014(9) Uiso 1 1 d
H22A H 0.590(5) 0.269(3) 0.9029(19) 0.025(11) Uiso 1 1 d
H22B H 0.688(8) 0.344(4) 0.874(3) 0.056(18) Uiso 1 1 d
H22C H 0.504(6) 0.341(3) 0.868(2) 0.029(12) Uiso 1 1 d
H23A H 0.378(6) 0.181(3) 0.749(2) 0.032(13) Uiso 1 1 d
H23B H 0.402(6) 0.157(3) 0.818(2) 0.038(14) Uiso 1 1 d
H23C H 0.310(6) 0.245(3) 0.797(2) 0.035(13) Uiso 1 1 d
H24A H 0.456(7) 0.368(4) 0.753(2) 0.048(15) Uiso 1 1 d
H24B H 0.539(6) 0.325(3) 0.701(2) 0.025(11) Uiso 1 1 d
H24C H 0.645(5) 0.383(2) 0.7507(17) 0.013(9) 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 W C1 97.16(10)
N8 W C2 100.12(10)
C1 W C2 38.74(9)
N8 W N2 90.15(10)
C1 W N2 157.20(9)
C2 W N2 159.83(10)
N8 W N4 98.33(10)
C1 W N4 123.77(9)
C2 W N4 85.31(9)
N2 W N4 76.00(8)
N8 W N6 174.65(9)
C1 W N6 87.61(9)
C2 W N6 85.11(9)
N2 W N6 84.52(9)
N4 W N6 80.89(9)
N8 W P 94.62(8)
C1 W P 78.37(7)
C2 W P 116.45(7)
N2 W P 79.54(6)
N4 W P 152.25(6)
N6 W P 83.95(6)
C24 P C23 101.41(15)
C24 P C22 98.69(16)
C23 P C22 103.43(17)
C24 P W 121.75(10)
C23 P W 115.43(11)
C22 P W 113.37(12)
C9 O1 C11 117.0(3)
C10 O4 C12 115.3(3)
C3 N1 C6 97.8(2)
C15 N2 N3 106.4(2)
C15 N2 W 130.1(2)
N3 N2 W 123.24(17)
C13 N3 N2 110.1(2)
C13 N3 B 130.1(3)
N2 N3 B 118.0(2)
C18 N4 N5 106.3(2)
C18 N4 W 132.6(2)
N5 N4 W 120.28(17)
C16 N5 N4 109.8(2)
C16 N5 B 127.8(2)
N4 N5 B 122.2(2)
C21 N6 N7 106.1(2)
C21 N6 W 133.3(2)
N7 N6 W 120.48(17)
C19 N7 N6 109.7(2)
C19 N7 B 128.6(3)
N6 N7 B 121.6(2)
O5 N8 W 176.5(2)
C2 C1 C6 103.9(2)
C2 C1 W 70.89(14)
C6 C1 W 125.33(17)
C1 C2 C3 104.1(2)
C1 C2 W 70.37(14)
C3 C2 W 129.02(17)
N1 C3 C7 113.0(2)
N1 C3 C2 104.6(2)
C7 C3 C2 118.3(2)
N1 C3 C4 98.9(2)
C7 C3 C4 116.4(2)
C2 C3 C4 103.2(2)
C9 C4 C5 112.5(2)
C9 C4 C3 113.1(2)
C5 C4 C3 101.8(2)
C10 C5 C4 113.5(2)
C10 C5 C6 114.6(2)
C4 C5 C6 102.7(2)
N1 C6 C8 110.4(2)
N1 C6 C1 105.8(2)
C8 C6 C1 120.6(2)
N1 C6 C5 97.56(19)
C8 C6 C5 116.1(2)
C1 C6 C5 103.5(2)
O2 C9 O1 123.6(3)
O2 C9 C4 126.6(3)
O1 C9 C4 109.8(3)
O3 C10 O4 122.7(3)
O3 C10 C5 126.3(3)
O4 C10 C5 111.0(2)
N3 C13 C14 108.7(3)
C13 C14 C15 104.5(2)
N2 C15 C14 110.3(3)
N5 C16 C17 108.9(3)
C16 C17 C18 104.1(3)
N4 C18 C17 111.0(3)
N7 C19 C20 108.3(3)
C19 C20 C21 105.1(3)
N6 C21 C20 110.8(3)
N7 B N5 109.1(2)
N7 B N3 108.7(2)
N5 B N3 105.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
W N8 1.775(2)
W C1 2.199(2)
W C2 2.206(3)
W N2 2.223(2)
W N4 2.245(2)
W N6 2.255(2)
W P 2.5213(7)
P C24 1.818(3)
P C23 1.821(3)
P C22 1.829(3)
O1 C9 1.346(4)
O1 C11 1.444(4)
O2 C9 1.202(4)
O3 C10 1.204(4)
O4 C10 1.349(4)
O4 C12 1.449(4)
O5 N8 1.237(3)
N1 C3 1.467(4)
N1 C6 1.473(3)
N2 C15 1.347(3)
N2 N3 1.355(4)
N3 C13 1.352(4)
N3 B 1.546(4)
N4 C18 1.340(4)
N4 N5 1.362(3)
N5 C16 1.346(4)
N5 B 1.543(4)
N6 C21 1.342(4)
N6 N7 1.369(3)
N7 C19 1.356(4)
N7 B 1.538(4)
C1 C2 1.461(4)
C1 C6 1.551(4)
C2 C3 1.550(4)
C3 C7 1.508(4)
C3 C4 1.588(4)
C4 C9 1.521(4)
C4 C5 1.544(4)
C5 C10 1.511(4)
C5 C6 1.569(4)
C6 C8 1.512(4)
C13 C14 1.378(5)
C14 C15 1.405(4)
C16 C17 1.385(5)
C17 C18 1.397(4)
C19 C20 1.378(5)
C20 C21 1.391(4)
