#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:25:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178715 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/26/4082600.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_4082600
loop_
_publ_author_name
'Pienkos, Jared A.'
'Knisely, Anne T.'
'Liebov, Benjamin K.'
'Teran, Victor'
'Zottig, Victor E.'
'Sabat, Michal'
'Myers, William H.'
'Harman, W. Dean'
_publ_section_title
;
 Tungsten-Mediated Selective Ring Opening of Vinylcyclopropanes
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              267
_journal_paper_doi               10.1021/om4010115
_journal_volume                  33
_journal_year                    2014
_chemical_formula_sum            'C22 H31 B N7 O2 P W'
_chemical_formula_weight         651.17
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.790(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.007(1)
_cell_length_b                   12.008(1)
_cell_length_c                   15.541(1)
_cell_measurement_reflns_used    6811
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      32.493
_cell_measurement_theta_min      2.168
_cell_volume                     2538.6(3)
_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      273(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32955
_diffrn_reflns_theta_full        32.51
_diffrn_reflns_theta_max         32.51
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    4.647
_exptl_absorpt_correction_T_max  0.801926
_exptl_absorpt_correction_T_min  0.426654
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         2.169
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         9130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0294
_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)+(0.0428P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0739
_reflns_number_gt                7241
_reflns_number_total             9130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4010115_si_002.cif
_cod_data_source_block           C22H31BN7O2PW
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z 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        2538.6(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4082600
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 0.257415(7) 0.157367(7) 0.033053(6) 0.03151(4) Uani 1 1 d .
P1 P 0.16052(6) 0.21211(7) 0.14422(5) 0.04410(16) Uani 1 1 d .
O1 O 0.09842(17) -0.0741(2) 0.11633(15) 0.0591(6) Uani 1 1 d .
O2 O 0.40048(18) 0.0232(2) 0.16611(16) 0.0636(6) Uani 1 1 d .
N1 N 0.35497(16) 0.18659(18) -0.05716(16) 0.0373(5) Uani 1 1 d .
N2 N 0.36077(17) 0.28852(19) -0.09368(15) 0.0393(5) Uani 1 1 d .
N3 N 0.16167(17) 0.28127(19) -0.05688(15) 0.0384(5) Uani 1 1 d .
N4 N 0.20261(18) 0.37665(19) -0.08030(16) 0.0400(5) Uani 1 1 d .
N5 N 0.34682(17) 0.30397(19) 0.08939(15) 0.0390(5) Uani 1 1 d .
N6 N 0.35542(17) 0.39483(18) 0.04027(16) 0.0403(5) Uani 1 1 d .
N7 N 0.34012(17) 0.07378(18) 0.10951(15) 0.0388(5) Uani 1 1 d .
C1 C 0.1494(2) -0.0608(2) 0.06292(18) 0.0442(6) Uani 1 1 d .
C2 C 0.1372(2) 0.0310(2) 0.00084(18) 0.0397(5) Uani 1 1 d .
C3 C 0.1928(2) 0.0302(2) -0.06732(17) 0.0377(5) Uani 1 1 d .
C4 C 0.2429(2) -0.0726(2) -0.08470(17) 0.0395(6) Uani 1 1 d .
C5 C 0.2584(3) -0.1569(2) -0.0254(2) 0.0469(7) Uani 1 1 d .
C6 C 0.2279(3) -0.1467(2) 0.0598(2) 0.0477(7) Uani 1 1 d .
H6A H 0.2858 -0.1290 0.1060 0.057 Uiso 1 1 calc R
H6B H 0.2043 -0.2188 0.0738 0.057 Uiso 1 1 calc R
C7 C 0.2671(3) -0.0838(3) -0.1726(2) 0.0557(8) Uani 1 1 d .
H7A H 0.3043 -0.0189 -0.1824 0.067 Uiso 1 1 calc R
H7B H 0.2063 -0.0845 -0.2183 0.067 Uiso 1 1 calc R
C8 C 0.3247(5) -0.1861(4) -0.1823(3) 0.110(2) Uani 1 1 d .
H8A H 0.3045 -0.2097 -0.2436 0.097 Uiso 1 1 calc R
H8B H 0.3933 -0.1647 -0.1714 0.097 Uiso 1 1 calc R
C9 C 0.3192(7) -0.2745(4) -0.1319(5) 0.075(4) Uani 1 1 d .
H9A H 0.3782 -0.3181 -0.1291 0.098 Uiso 1 1 calc R
H9B H 0.2644 -0.3191 -0.1638 0.098 Uiso 1 1 calc R
C10 C 0.3082(3) -0.2636(3) -0.0408(2) 0.0650(9) Uani 1 1 d .
H10A H 0.3727 -0.2667 -0.0004 0.078 Uiso 1 1 calc R
H10B H 0.2703 -0.3261 -0.0275 0.078 Uiso 1 1 calc R
C11 C 0.4265(2) 0.2837(3) -0.1436(2) 0.0490(7) Uani 1 1 d .
H11 H 0.4436 0.3428 -0.1757 0.059 Uiso 1 1 calc R
C12 C 0.4644(3) 0.1793(3) -0.1402(3) 0.0563(8) Uani 1 1 d .
H12 H 0.5114 0.1530 -0.1685 0.068 Uiso 1 1 calc R
C13 C 0.4177(2) 0.1206(3) -0.0852(2) 0.0462(6) Uani 1 1 d .
H13 H 0.4286 0.0460 -0.0700 0.055 Uiso 1 1 calc R
C14 C 0.1304(2) 0.4416(3) -0.1273(2) 0.0541(8) Uani 1 1 d .
H14 H 0.1393 0.5110 -0.1508 0.065 Uiso 1 1 calc R
C15 C 0.0418(2) 0.3897(3) -0.1350(2) 0.0594(9) Uani 1 1 d .
H15 H -0.0200 0.4157 -0.1640 0.071 Uiso 1 1 calc R
C16 C 0.0647(2) 0.2894(3) -0.0901(2) 0.0475(7) Uani 1 1 d .
H16 H 0.0189 0.2356 -0.0840 0.057 Uiso 1 1 calc R
C17 C 0.4177(2) 0.4677(2) 0.0913(2) 0.0511(7) Uani 1 1 d .
H17 H 0.4361 0.5364 0.0728 0.061 Uiso 1 1 calc R
C18 C 0.4493(3) 0.4242(3) 0.1744(2) 0.0574(8) Uani 1 1 d .
H18 H 0.4920 0.4567 0.2230 0.069 Uiso 1 1 calc R
C19 C 0.4037(2) 0.3209(3) 0.1706(2) 0.0489(7) Uani 1 1 d .
H19 H 0.4116 0.2710 0.2176 0.059 Uiso 1 1 calc R
C20 C 0.0292(3) 0.1876(3) 0.1223(3) 0.0678(10) Uani 1 1 d .
H20C H 0.0166 0.1090 0.1181 0.084 Uiso 1 1 calc R
H20A H -0.0028 0.2228 0.0676 0.084 Uiso 1 1 calc R
H20B H 0.0042 0.2181 0.1697 0.084 Uiso 1 1 calc R
C21 C 0.2060(3) 0.1472(3) 0.2511(2) 0.0674(11) Uani 1 1 d .
H21B H 0.1724 0.1778 0.2928 0.089 Uiso 1 1 calc R
H21A H 0.2753 0.1610 0.2713 0.089 Uiso 1 1 calc R
H21C H 0.1945 0.0684 0.2460 0.089 Uiso 1 1 calc R
C22 C 0.1661(3) 0.3596(3) 0.1692(3) 0.0714(12) Uani 1 1 d .
H22C H 0.1313 0.3743 0.2143 0.092 Uiso 1 1 calc R
H22A H 0.1364 0.4007 0.1167 0.092 Uiso 1 1 calc R
H22B H 0.2335 0.3819 0.1900 0.092 Uiso 1 1 calc R
B1 B 0.3137(2) 0.3913(3) -0.0604(2) 0.0404(6) Uani 1 1 d .
H1B H 0.3336(19) 0.469(2) -0.0946(18) 0.037(7) Uiso 1 1 d .
H2 H 0.077(2) 0.057(2) -0.0128(19) 0.039(8) Uiso 1 1 d .
H3 H 0.1643(16) 0.0629(19) -0.1182(16) 0.017(5) 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
N7 W N1 96.42(10)
N7 W C3 100.07(10)
N1 W C3 82.71(9)
N7 W N5 88.13(9)
N1 W N5 75.37(8)
C3 W N5 157.35(10)
N7 W C2 95.94(10)
N1 W C2 120.91(9)
C3 W C2 38.23(10)
N5 W C2 162.41(10)
N7 W N3 173.36(9)
N1 W N3 82.42(8)
C3 W N3 86.29(9)
N5 W N3 85.25(8)
C2 W N3 90.23(9)
N7 W P1 93.50(8)
N1 W P1 155.30(6)
C3 W P1 117.72(8)
N5 W P1 82.43(6)
C2 W P1 80.25(8)
N3 W P1 85.12(6)
C21 P1 C22 103.7(2)
C21 P1 C20 102.8(2)
C22 P1 C20 100.9(2)
C21 P1 W 112.79(14)
C22 P1 W 113.51(13)
C20 P1 W 121.07(13)
C13 N1 N2 106.8(2)
C13 N1 W 132.1(2)
N2 N1 W 121.06(16)
C11 N2 N1 108.7(2)
C11 N2 B1 129.5(2)
N1 N2 B1 120.4(2)
C16 N3 N4 106.7(2)
C16 N3 W 133.4(2)
N4 N3 W 119.51(17)
C14 N4 N3 108.7(2)
C14 N4 B1 130.0(3)
N3 N4 B1 121.0(2)
C19 N5 N6 107.2(2)
C19 N5 W 130.3(2)
N6 N5 W 122.38(17)
C17 N6 N5 108.8(2)
C17 N6 B1 130.7(2)
N5 N6 B1 119.3(2)
O2 N7 W 175.0(2)
O1 C1 C2 123.7(3)
O1 C1 C6 118.4(3)
C2 C1 C6 117.8(3)
C1 C2 C3 118.8(3)
C1 C2 W 113.89(18)
C3 C2 W 70.23(15)
C2 C3 C4 119.9(2)
C2 C3 W 71.54(15)
C4 C3 W 124.95(18)
C5 C4 C3 120.5(3)
C5 C4 C7 121.5(3)
C3 C4 C7 117.8(2)
C4 C5 C6 120.7(3)
C4 C5 C10 122.3(3)
C6 C5 C10 117.0(3)
C5 C6 C1 116.7(2)
C4 C7 C8 114.4(3)
C9 C8 C7 119.1(5)
C8 C9 C10 122.0(5)
C9 C10 C5 112.9(3)
N2 C11 C12 109.5(3)
C11 C12 C13 104.8(3)
N1 C13 C12 110.1(3)
N4 C14 C15 109.4(3)
C14 C15 C16 104.8(3)
N3 C16 C15 110.4(3)
N6 C17 C18 109.0(3)
C17 C18 C19 105.0(3)
N5 C19 C18 109.9(3)
N4 B1 N6 109.4(2)
N4 B1 N2 109.7(2)
N6 B1 N2 105.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
W N7 1.762(2)
W N1 2.207(2)
W C3 2.216(3)
W N5 2.216(2)
W C2 2.233(3)
W N3 2.252(2)
W P1 2.5252(8)
P1 C21 1.808(4)
P1 C22 1.811(3)
P1 C20 1.814(4)
O1 C1 1.227(3)
O2 N7 1.226(3)
N1 C13 1.331(4)
N1 N2 1.360(3)
N2 C11 1.340(3)
N2 B1 1.546(4)
N3 C16 1.337(4)
N3 N4 1.368(3)
N4 C14 1.347(4)
N4 B1 1.523(4)
N5 C19 1.338(4)
N5 N6 1.353(3)
N6 C17 1.351(3)
N6 B1 1.534(4)
C1 C2 1.447(4)
C1 C6 1.518(4)
C2 C3 1.457(4)
C3 C4 1.476(4)
C4 C5 1.352(4)
C4 C7 1.489(4)
C5 C6 1.489(5)
C5 C10 1.505(4)
C7 C8 1.496(5)
C8 C9 1.332(7)
C9 C10 1.466(6)
C11 C12 1.357(4)
C12 C13 1.387(5)
C14 C15 1.368(5)
C15 C16 1.391(5)
C17 C18 1.365(5)
C18 C19 1.390(4)
