#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:55:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178707 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/18/4081800.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_4081800
loop_
_publ_author_name
'Breunig, Jens Michael'
'Hübner, Alexander'
'Bolte, Michael'
'Wagner, Matthias'
'Lerner, Hans-Wolfram'
_publ_section_title
;
 Reactivity of Phosphaboradibenzofulvene toward Hydrogen, Acetonitrile,
 Benzophenone, and 2,3-Dimethylbutadiene
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              6792
_journal_paper_doi               10.1021/om400553j
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C20 H28 B P'
_chemical_formula_sum            'C20 H28 B P'
_chemical_formula_weight         310.20
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.919(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3141(5)
_cell_length_b                   10.1097(6)
_cell_length_c                   18.1282(8)
_cell_measurement_reflns_used    21548
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.8
_cell_measurement_theta_min      3.4
_cell_volume                     1867.42(17)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_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  0.0808
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23756
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_min         3.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.9748
_exptl_absorpt_correction_T_min  0.9427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0561P)²+0.1485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                3181
_reflns_number_total             3796
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om400553j_si_002.cif
_cod_data_source_block           wa1266
_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 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4081800
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
P1 P 0.41054(3) 0.56035(3) 0.219801(19) 0.02591(11) Uani 1 1 d .
H1P H 0.3394(15) 0.6483(15) 0.2507(8) 0.029(4) Uiso 1 1 d .
B1 B 0.30476(15) 0.39758(15) 0.20186(9) 0.0283(3) Uani 1 1 d .
H1B H 0.3200(15) 0.3481(16) 0.2581(9) 0.033(4) Uiso 1 1 d .
C1 C 0.33318(13) 0.30256(13) 0.13443(8) 0.0282(3) Uani 1 1 d .
C2 C 0.21695(14) 0.29179(13) 0.08197(8) 0.0286(3) Uani 1 1 d .
C3 C 0.21011(15) 0.21055(14) 0.01927(8) 0.0348(3) Uani 1 1 d .
H3 H 0.1314 0.2052 -0.0156 0.042 Uiso 1 1 calc R
C4 C 0.31945(16) 0.13776(15) 0.00840(9) 0.0374(3) Uani 1 1 d .
H4 H 0.3155 0.0816 -0.0339 0.045 Uiso 1 1 calc R
C5 C 0.43468(16) 0.14657(14) 0.05912(9) 0.0370(3) Uani 1 1 d .
H5 H 0.5092 0.0965 0.0512 0.044 Uiso 1 1 calc R
C6 C 0.44185(15) 0.22828(14) 0.12146(8) 0.0331(3) Uani 1 1 d .
H6 H 0.5215 0.2336 0.1556 0.040 Uiso 1 1 calc R
C11 C 0.15460(13) 0.43918(13) 0.17216(8) 0.0277(3) Uani 1 1 d .
C12 C 0.11092(13) 0.37337(13) 0.10403(8) 0.0277(3) Uani 1 1 d .
C13 C -0.01619(14) 0.39089(15) 0.06597(8) 0.0335(3) Uani 1 1 d .
H13 H -0.0443 0.3453 0.0205 0.040 Uiso 1 1 calc R
C14 C -0.10092(15) 0.47531(15) 0.09514(9) 0.0371(3) Uani 1 1 d .
H14 H -0.1876 0.4881 0.0695 0.044 Uiso 1 1 calc R
C15 C -0.05949(14) 0.54146(15) 0.16191(9) 0.0363(3) Uani 1 1 d .
H15 H -0.1181 0.5995 0.1815 0.044 Uiso 1 1 calc R
C16 C 0.06732(14) 0.52335(14) 0.20038(8) 0.0330(3) Uani 1 1 d .
H16 H 0.0942 0.5687 0.2461 0.040 Uiso 1 1 calc R
C21 C 0.44382(14) 0.65077(14) 0.13541(8) 0.0307(3) Uani 1 1 d .
C22 C 0.47448(17) 0.79756(15) 0.15209(9) 0.0410(4) Uani 1 1 d .
H22A H 0.4018 0.8381 0.1729 0.061 Uiso 1 1 calc R
H22B H 0.4858 0.8431 0.1058 0.061 Uiso 1 1 calc R
H22C H 0.5554 0.8050 0.1882 0.061 Uiso 1 1 calc R
C23 C 0.31695(16) 0.64399(17) 0.07849(9) 0.0425(4) Uani 1 1 d .
H23A H 0.2455 0.6868 0.0994 0.064 Uiso 1 1 calc R
H23B H 0.2943 0.5513 0.0672 0.064 Uiso 1 1 calc R
H23C H 0.3302 0.6896 0.0325 0.064 Uiso 1 1 calc R
C24 C 0.55502(16) 0.58398(16) 0.10217(9) 0.0413(4) Uani 1 1 d .
H24A H 0.6362 0.5882 0.1382 0.062 Uiso 1 1 calc R
H24B H 0.5677 0.6298 0.0562 0.062 Uiso 1 1 calc R
H24C H 0.5322 0.4913 0.0909 0.062 Uiso 1 1 calc R
C31 C 0.55539(14) 0.53743(14) 0.29391(8) 0.0326(3) Uani 1 1 d .
C32 C 0.49898(17) 0.51620(17) 0.36664(8) 0.0420(4) Uani 1 1 d .
H32A H 0.4502 0.5952 0.3775 0.063 Uiso 1 1 calc R
H32B H 0.5709 0.5001 0.4078 0.063 Uiso 1 1 calc R
H32C H 0.4399 0.4398 0.3610 0.063 Uiso 1 1 calc R
C33 C 0.64742(16) 0.65776(17) 0.30359(10) 0.0435(4) Uani 1 1 d .
H33A H 0.5980 0.7363 0.3145 0.065 Uiso 1 1 calc R
H33B H 0.6841 0.6721 0.2575 0.065 Uiso 1 1 calc R
H33C H 0.7189 0.6416 0.3449 0.065 Uiso 1 1 calc R
C34 C 0.63151(16) 0.41322(17) 0.27758(10) 0.0431(4) Uani 1 1 d .
H34A H 0.6681 0.4260 0.2313 0.065 Uiso 1 1 calc R
H34B H 0.5721 0.3370 0.2720 0.065 Uiso 1 1 calc R
H34C H 0.7030 0.3973 0.3190 0.065 Uiso 1 1 calc R
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'
P P 0.1023 0.0942 '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
C21 P1 C31 115.15(7)
C21 P1 B1 116.25(6)
C31 P1 B1 112.11(7)
C21 P1 H1P 101.6(7)
C31 P1 H1P 102.3(6)
B1 P1 H1P 107.5(7)
C11 B1 C1 100.35(11)
C11 B1 P1 108.36(9)
C1 B1 P1 117.36(10)
C11 B1 H1B 114.2(8)
C1 B1 H1B 113.9(8)
P1 B1 H1B 103.0(8)
C6 C1 C2 117.61(13)
C6 C1 B1 133.62(13)
C2 C1 B1 108.66(11)
C3 C2 C1 121.58(13)
C3 C2 C12 127.20(13)
C1 C2 C12 111.21(12)
C4 C3 C2 119.27(14)
C4 C3 H3 120.4
C2 C3 H3 120.4
C3 C4 C5 120.25(14)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 120.52(14)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C1 120.78(14)
C5 C6 H6 119.6
C1 C6 H6 119.6
C16 C11 C12 118.16(13)
C16 C11 B1 132.69(13)
C12 C11 B1 109.15(12)
C13 C12 C11 121.34(13)
C13 C12 C2 128.09(13)
C11 C12 C2 110.56(12)
C14 C13 C12 119.35(13)
C14 C13 H13 120.3
C12 C13 H13 120.3
C13 C14 C15 120.14(14)
C13 C14 H14 119.9
C15 C14 H14 119.9
C14 C15 C16 120.63(14)
C14 C15 H15 119.7
C16 C15 H15 119.7
C11 C16 C15 120.39(13)
C11 C16 H16 119.8
C15 C16 H16 119.8
C24 C21 C23 109.12(13)
C24 C21 C22 111.03(12)
C23 C21 C22 107.63(12)
C24 C21 P1 110.60(10)
C23 C21 P1 106.49(10)
C22 C21 P1 111.80(10)
C21 C22 H22A 109.5
C21 C22 H22B 109.5
H22A C22 H22B 109.5
C21 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C21 C23 H23A 109.5
C21 C23 H23B 109.5
H23A C23 H23B 109.5
C21 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
C21 C24 H24A 109.5
C21 C24 H24B 109.5
H24A C24 H24B 109.5
C21 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
C34 C31 C33 110.16(13)
C34 C31 C32 108.94(13)
C33 C31 C32 108.79(13)
C34 C31 P1 109.87(10)
C33 C31 P1 113.34(10)
C32 C31 P1 105.56(10)
C31 C32 H32A 109.5
C31 C32 H32B 109.5
H32A C32 H32B 109.5
C31 C32 H32C 109.5
H32A C32 H32C 109.5
H32B C32 H32C 109.5
C31 C33 H33A 109.5
C31 C33 H33B 109.5
H33A C33 H33B 109.5
C31 C33 H33C 109.5
H33A C33 H33C 109.5
H33B C33 H33C 109.5
C31 C34 H34A 109.5
C31 C34 H34B 109.5
H34A C34 H34B 109.5
C31 C34 H34C 109.5
H34A C34 H34C 109.5
H34B C34 H34C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C21 1.8593(14)
P1 C31 1.8624(14)
P1 B1 1.9733(16)
P1 H1P 1.330(15)
B1 C11 1.615(2)
B1 C1 1.617(2)
B1 H1B 1.125(16)
C1 C6 1.399(2)
C1 C2 1.4142(19)
C2 C3 1.395(2)
C2 C12 1.4737(19)
C3 C4 1.386(2)
C3 H3 0.9500
C4 C5 1.388(2)
C4 H4 0.9500
C5 C6 1.393(2)
C5 H5 0.9500
C6 H6 0.9500
C11 C16 1.392(2)
C11 C12 1.4137(19)
C12 C13 1.3949(19)
C13 C14 1.384(2)
C13 H13 0.9500
C14 C15 1.391(2)
C14 H14 0.9500
C15 C16 1.396(2)
C15 H15 0.9500
C16 H16 0.9500
C21 C24 1.533(2)
C21 C23 1.537(2)
C21 C22 1.538(2)
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
C24 H24A 0.9800
C24 H24B 0.9800
C24 H24C 0.9800
C31 C34 1.534(2)
C31 C33 1.536(2)
C31 C32 1.536(2)
C32 H32A 0.9800
C32 H32B 0.9800
C32 H32C 0.9800
C33 H33A 0.9800
C33 H33B 0.9800
C33 H33C 0.9800
C34 H34A 0.9800
C34 H34B 0.9800
C34 H34C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C21 P1 B1 C11 -72.79(11)
C31 P1 B1 C11 151.83(9)
C21 P1 B1 C1 39.85(13)
C31 P1 B1 C1 -95.53(11)
C11 B1 C1 C6 -178.61(14)
P1 B1 C1 C6 64.32(19)
C11 B1 C1 C2 -2.67(14)
P1 B1 C1 C2 -119.74(11)
C6 C1 C2 C3 -0.2(2)
B1 C1 C2 C3 -176.87(13)
C6 C1 C2 C12 178.82(12)
B1 C1 C2 C12 2.13(15)
C1 C2 C3 C4 0.6(2)
C12 C2 C3 C4 -178.28(13)
C2 C3 C4 C5 -0.5(2)
C3 C4 C5 C6 0.1(2)
C4 C5 C6 C1 0.3(2)
C2 C1 C6 C5 -0.2(2)
B1 C1 C6 C5 175.43(14)
C1 B1 C11 C16 -177.44(14)
P1 B1 C11 C16 -53.87(18)
C1 B1 C11 C12 2.38(14)
P1 B1 C11 C12 125.94(10)
C16 C11 C12 C13 -0.4(2)
B1 C11 C12 C13 179.71(12)
C16 C11 C12 C2 178.51(12)
B1 C11 C12 C2 -1.33(15)
C3 C2 C12 C13 -2.7(2)
C1 C2 C12 C13 178.35(14)
C3 C2 C12 C11 178.41(13)
C1 C2 C12 C11 -0.52(16)
C11 C12 C13 C14 0.6(2)
C2 C12 C13 C14 -178.18(14)
C12 C13 C14 C15 -0.2(2)
C13 C14 C15 C16 -0.2(2)
C12 C11 C16 C15 0.0(2)
B1 C11 C16 C15 179.76(14)
C14 C15 C16 C11 0.4(2)
C31 P1 C21 C24 54.98(12)
B1 P1 C21 C24 -79.05(12)
C31 P1 C21 C23 173.41(10)
B1 P1 C21 C23 39.38(12)
C31 P1 C21 C22 -69.30(12)
B1 P1 C21 C22 156.67(11)
C21 P1 C31 C34 -85.54(13)
B1 P1 C31 C34 50.35(13)
C21 P1 C31 C33 38.17(13)
B1 P1 C31 C33 174.07(11)
C21 P1 C31 C32 157.14(10)
B1 P1 C31 C32 -66.96(11)
