#------------------------------------------------------------------------------
#$Date: 2016-03-21 12:56:03 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178689 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/00/4080023.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_4080023
loop_
_publ_author_name
'Pienkos, Jared A.'
'Zottig, Victor E.'
'Iovan, Diana A.'
'Li, Mengxun'
'Harrison, Daniel P.'
'Sabat, Michal'
'Salomon, Rebecca J.'
'Strausberg, Laura'
'Teran, Victor A.'
'Myers, William H.'
'Harman, W. Dean'
_publ_section_title
;
 Friedel--Crafts Ring-Coupling Reactions Promoted by Tungsten
 Dearomatization Agent
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              691
_journal_paper_doi               10.1021/om3012008
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C30 H34 B N8 O P W'
_chemical_formula_weight         748.28
_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                 107.696(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0361(3)
_cell_length_b                   19.7005(6)
_cell_length_c                   16.0296(5)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      33.73
_cell_measurement_theta_min      2.38
_cell_volume                     3019.35(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33799
_diffrn_reflns_theta_full        35.98
_diffrn_reflns_theta_max         35.98
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    3.918
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.2716
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.520
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         9577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0225
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                8281
_reflns_number_total             14208
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om3012008_si_002.cif
_cod_data_source_block           C30H34BN8OPW
_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 1891 2012-01-12 08:04:46Z andrius 

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_cell_volume        3019.4(2)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4080023
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 0.816596(8) 0.830155(4) 0.108077(5) 0.01285(4) Uani 1 1 d .
P1 P 0.88838(6) 0.72341(3) 0.19597(4) 0.01823(11) Uani 1 1 d .
O1 O 0.90240(18) 0.77515(10) -0.04245(10) 0.0250(4) Uani 1 1 d .
N1 N 0.1760(2) 0.71915(11) 0.00512(14) 0.0227(4) Uani 1 1 d .
N2 N 1.0354(2) 0.86304(10) 0.17401(12) 0.0178(4) Uani 1 1 d .
N3 N 1.0642(2) 0.92280(10) 0.21878(12) 0.0203(4) Uani 1 1 d .
N4 N 0.7813(2) 0.87979(9) 0.22673(11) 0.0185(4) Uani 1 1 d .
N5 N 0.8407(2) 0.94140(10) 0.25510(12) 0.0187(4) Uani 1 1 d .
N6 N 0.8203(2) 0.93491(9) 0.06082(12) 0.0190(4) Uani 1 1 d .
N7 N 0.8731(2) 0.98775(10) 0.11629(13) 0.0213(4) Uani 1 1 d .
N8 N 0.86188(19) 0.79615(9) 0.01840(11) 0.0157(3) Uani 1 1 d .
C1 C 0.5562(2) 0.71673(11) 0.02823(14) 0.0173(4) Uani 1 1 d .
H1 H 0.6106 0.6771 0.0562 0.021 Uiso 1 1 calc R
C2 C 0.6106(2) 0.77866(11) 0.08612(13) 0.0162(4) Uani 1 1 d .
C3 C 0.5886(3) 0.84425(12) 0.04381(16) 0.0181(4) Uani 1 1 d .
C4 C 0.5277(2) 0.84935(13) -0.05188(15) 0.0204(4) Uani 1 1 d .
C5 C 0.4732(3) 0.91096(15) -0.09113(18) 0.0320(6) Uani 1 1 d .
H5 H 0.4760 0.9492 -0.0566 0.038 Uiso 1 1 calc R
C6 C 0.4145(3) 0.91542(18) -0.1819(2) 0.0430(7) Uani 1 1 d .
H6 H 0.3807 0.9569 -0.2074 0.052 Uiso 1 1 calc R
C7 C 0.4062(3) 0.8595(2) -0.23353(18) 0.0419(7) Uani 1 1 d .
H7 H 0.3677 0.8629 -0.2940 0.050 Uiso 1 1 calc R
C8 C 0.4551(3) 0.79765(17) -0.19564(16) 0.0315(6) Uani 1 1 d .
H8 H 0.4466 0.7594 -0.2308 0.038 Uiso 1 1 calc R
C9 C 0.5170(2) 0.79191(13) -0.10553(14) 0.0207(4) Uani 1 1 d .
C10 C 0.5733(2) 0.72498(12) -0.06391(15) 0.0201(4) Uani 1 1 d .
H10A H 0.6717 0.7217 -0.0594 0.024 Uiso 1 1 calc R
H10B H 0.5246 0.6883 -0.1012 0.024 Uiso 1 1 calc R
C11 C 0.4048(2) 0.70378(11) 0.01992(14) 0.0185(4) Uani 1 1 d .
C12 C 0.3338(2) 0.63972(11) 0.00043(13) 0.0168(4) Uani 1 1 d .
C13 C 0.3769(2) 0.57327(12) -0.01039(15) 0.0217(4) Uani 1 1 d .
H13 H 0.4704 0.5640 -0.0038 0.026 Uiso 1 1 calc R
C14 C 0.2785(3) 0.52197(12) -0.03098(16) 0.0243(5) Uani 1 1 d .
H14 H 0.3065 0.4779 -0.0381 0.029 Uiso 1 1 calc R
C15 C 0.1373(3) 0.53513(13) -0.04128(15) 0.0232(5) Uani 1 1 d .
H15 H 0.0731 0.4997 -0.0554 0.028 Uiso 1 1 calc R
C16 C 0.0917(2) 0.59970(13) -0.03084(15) 0.0221(4) Uani 1 1 d .
H16 H -0.0021 0.6085 -0.0378 0.027 Uiso 1 1 calc R
C17 C 0.1914(2) 0.65120(13) -0.00952(14) 0.0186(4) Uani 1 1 d .
C18 C 0.3041(2) 0.75026(12) 0.02127(15) 0.0205(4) Uani 1 1 d .
H18 H 0.3201 0.7964 0.0317 0.025 Uiso 1 1 calc R
C19 C 1.2030(3) 0.93179(14) 0.24955(16) 0.0273(5) Uani 1 1 d .
H19 H 1.2480 0.9689 0.2819 0.033 Uiso 1 1 calc R
C20 C 1.2679(3) 0.87685(14) 0.22532(15) 0.0269(5) Uani 1 1 d .
H20 H 1.3634 0.8692 0.2378 0.032 Uiso 1 1 calc R
C21 C 1.1591(3) 0.83552(11) 0.17818(17) 0.0215(5) Uani 1 1 d .
H21 H 1.1707 0.7943 0.1529 0.026 Uiso 1 1 calc R
C22 C 0.7957(3) 0.96395(12) 0.32095(14) 0.0219(4) Uani 1 1 d .
H22 H 0.8208 1.0049 0.3505 0.026 Uiso 1 1 calc R
C23 C 0.7062(3) 0.91651(13) 0.33751(15) 0.0250(5) Uani 1 1 d .
H23 H 0.6599 0.9185 0.3797 0.030 Uiso 1 1 calc R
C24 C 0.7005(3) 0.86501(13) 0.27715(14) 0.0229(4) Uani 1 1 d .
H24 H 0.6477 0.8256 0.2724 0.027 Uiso 1 1 calc R
C25 C 0.8727(3) 1.04405(12) 0.06865(18) 0.0308(6) Uani 1 1 d .
H25 H 0.9037 1.0867 0.0913 0.037 Uiso 1 1 calc R
C26 C 0.8195(3) 1.02859(14) -0.01843(18) 0.0320(6) Uani 1 1 d .
H26 H 0.8069 1.0577 -0.0659 0.038 Uiso 1 1 calc R
C27 C 0.7885(3) 0.95962(13) -0.02028(16) 0.0245(5) Uani 1 1 d .
H27 H 0.7509 0.9343 -0.0710 0.029 Uiso 1 1 calc R
C28 C 0.7703(3) 0.67962(14) 0.24529(19) 0.0278(6) Uani 1 1 d .
H28A H 0.8085 0.6360 0.2664 0.042 Uiso 1 1 calc R
H28B H 0.6807 0.6738 0.2022 0.042 Uiso 1 1 calc R
H28C H 0.7598 0.7061 0.2932 0.042 Uiso 1 1 calc R
C29 C 0.9349(4) 0.65755(14) 0.1299(2) 0.0325(6) Uani 1 1 d .
H29A H 0.8568 0.6489 0.0789 0.049 Uiso 1 1 calc R
H29B H 0.9591 0.6167 0.1638 0.049 Uiso 1 1 calc R
H29C H 1.0134 0.6724 0.1122 0.049 Uiso 1 1 calc R
C30 C 1.0426(3) 0.72917(16) 0.29203(18) 0.0350(6) Uani 1 1 d .
H30A H 1.1253 0.7301 0.2737 0.052 Uiso 1 1 calc R
H30B H 1.0459 0.6905 0.3291 0.052 Uiso 1 1 calc R
H30C H 1.0379 0.7699 0.3238 0.052 Uiso 1 1 calc R
B1 B 0.9454(3) 0.97418(13) 0.21382(16) 0.0205(5) Uani 1 1 d .
H1B H 0.986(3) 1.0235(12) 0.2525(15) 0.007(5) Uiso 1 1 d .
H1N H 0.103(4) 0.736(2) -0.011(3) 0.053(12) Uiso 1 1 d .
H2 H 0.580(3) 0.7775(14) 0.1378(18) 0.021(7) Uiso 1 1 d .
H3 H 0.565(3) 0.8835(14) 0.0764(17) 0.014(6) 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 N6 92.31(8)
N8 W C3 98.83(9)
N6 W C3 81.14(8)
N8 W N2 92.07(8)
N6 W N2 76.89(7)
C3 W N2 155.82(8)
N8 W C2 98.87(8)
N6 W C2 118.89(8)
C3 W C2 37.85(8)
N2 W C2 160.11(7)
N8 W N4 173.70(8)
N6 W N4 84.68(7)
C3 W N4 86.19(8)
N2 W N4 81.87(7)
C2 W N4 87.42(7)
N8 W P1 92.18(6)
N6 W P1 160.99(5)
C3 W P1 116.35(7)
N2 W P1 84.49(5)
C2 W P1 78.58(6)
N4 W P1 88.95(5)
C29 P1 C30 103.47(16)
C29 P1 C28 103.26(14)
C30 P1 C28 99.18(13)
C29 P1 W 110.52(9)
C30 P1 W 116.50(10)
C28 P1 W 121.64(10)
C17 N1 C18 108.5(2)
C21 N2 N3 106.14(19)
C21 N2 W 132.30(16)
N3 N2 W 121.52(14)
C19 N3 N2 109.8(2)
C19 N3 B1 129.1(2)
N2 N3 B1 120.05(18)
C24 N4 N5 105.95(18)
C24 N4 W 133.79(15)
N5 N4 W 120.00(14)
C22 N5 N4 109.76(19)
C22 N5 B1 129.3(2)
N4 N5 B1 120.90(18)
C27 N6 N7 106.67(19)
C27 N6 W 130.81(16)
N7 N6 W 122.24(13)
C25 N7 N6 108.95(19)
C25 N7 B1 129.8(2)
N6 N7 B1 120.01(18)
O1 N8 W 175.32(17)
C11 C1 C2 110.71(17)
C11 C1 C10 109.60(18)
C2 C1 C10 111.88(18)
C3 C2 C1 116.94(19)
C3 C2 W 70.72(13)
C1 C2 W 126.94(14)
C2 C3 C4 120.4(2)
C2 C3 W 71.44(13)
C4 C3 W 122.31(17)
C5 C4 C9 118.5(2)
C5 C4 C3 120.6(2)
C9 C4 C3 120.9(2)
C6 C5 C4 120.4(3)
C7 C6 C5 120.6(3)
C6 C7 C8 119.8(3)
C7 C8 C9 120.9(3)
C8 C9 C4 119.8(2)
C8 C9 C10 121.3(2)
C4 C9 C10 119.0(2)
C9 C10 C1 112.26(18)
C18 C11 C12 105.7(2)
C18 C11 C1 127.9(2)
C12 C11 C1 126.1(2)
C13 C12 C17 118.4(2)
C13 C12 C11 133.9(2)
C17 C12 C11 107.7(2)
C14 C13 C12 119.1(2)
C13 C14 C15 121.1(2)
C16 C15 C14 121.2(2)
C15 C16 C17 117.5(2)
N1 C17 C16 129.9(2)
N1 C17 C12 107.5(2)
C16 C17 C12 122.7(2)
C11 C18 N1 110.6(2)
N3 C19 C20 108.7(2)
C19 C20 C21 104.6(2)
N2 C21 C20 110.8(2)
N5 C22 C23 108.8(2)
C22 C23 C24 104.6(2)
N4 C24 C23 110.9(2)
N7 C25 C26 109.2(2)
C25 C26 C27 104.7(2)
N6 C27 C26 110.5(2)
N7 B1 N5 109.70(19)
N7 B1 N3 106.55(19)
N5 B1 N3 108.57(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
W N8 1.7660(18)
W N6 2.2026(18)
W C3 2.223(2)
W N2 2.2241(19)
W C2 2.232(2)
W N4 2.2601(18)
W P1 2.5118(6)
P1 C29 1.823(3)
P1 C30 1.825(3)
P1 C28 1.828(3)
O1 N8 1.237(2)
N1 C17 1.376(3)
N1 C18 1.377(3)
N2 C21 1.338(3)
N2 N3 1.363(3)
N3 C19 1.340(3)
N3 B1 1.548(3)
N4 C24 1.339(3)
N4 N5 1.368(3)
N5 C22 1.344(3)
N5 B1 1.543(3)
N6 C27 1.333(3)
N6 N7 1.367(3)
N7 C25 1.346(3)
N7 B1 1.534(3)
C1 C11 1.506(3)
C1 C2 1.530(3)
C1 C10 1.547(3)
C2 C3 1.445(3)
C3 C4 1.472(3)
C4 C5 1.400(4)
C4 C9 1.406(3)
C5 C6 1.397(4)
C6 C7 1.366(5)
C7 C8 1.383(5)
C8 C9 1.393(3)
C9 C10 1.508(3)
C11 C18 1.369(3)
C11 C12 1.436(3)
C12 C13 1.406(3)
C12 C17 1.407(3)
C13 C14 1.381(3)
C14 C15 1.400(3)
C15 C16 1.379(4)
C16 C17 1.393(3)
C19 C20 1.379(4)
C20 C21 1.387(3)
C22 C23 1.377(4)
C23 C24 1.391(3)
C25 C26 1.369(4)
C26 C27 1.392(4)
