#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/49/7104944.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_7104944
loop_
_publ_author_name
'Shimada, Shigeru'
'Maruyama, Junpei'
'Choe, Yoong-Kee'
'Yamashita, Takashi'
_publ_section_title
;
 A unique Bi-Bi bond forming reaction using organobismuth oxides and
 phosphorus compounds bearing a P(=O)H group.
;
_journal_issue                   41
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6168
_journal_page_last               6170
_journal_paper_doi               10.1039/b914316e
_journal_year                    2009
_chemical_formula_moiety         'C36 H42 Bi2 N2, 2(C7 H8) '
_chemical_formula_sum            'C50 H58 Bi2 N2'
_chemical_formula_weight         1104.98
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_date             2008-01-13
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                90.0000
_cell_angle_beta                 98.708(1)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.5702(4)
_cell_length_b                   14.2358(6)
_cell_length_c                   15.7621(7)
_cell_measurement_reflns_used    6950
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.6
_cell_volume                     2122.67(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    'DIRDIF99 (PATTY)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean '8.366 [pixels/mm]'
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12618
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.21
_exptl_absorpt_coefficient_mu    8.300
_exptl_absorpt_correction_T_max  0.517
_exptl_absorpt_correction_T_min  0.456
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS; Sheldrick 1996
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1076.00
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.73
_refine_diff_density_min         -0.51
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4719
_refine_ls_R_factor_gt           0.0178
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[0.3300σ(Fo²) + 0.0800]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0411
_reflns_number_gt                4103
_reflns_number_total             4719
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            b914316e.txt
_cod_data_source_block           compound-1a
_cod_original_formula_sum        'C50 H58 Bi2 N2 '
_cod_database_code               7104944
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi(1) Bi 0.032210(10) 0.081030(10) 0.063970(10) 0.01466(2) Uani 1.00 1 d . . .
N(1) N 0.0522(2) 0.16135(17) 0.23402(16) 0.0181(6) Uani 1.00 1 d . . .
C(1) C -0.1759(2) 0.0659(2) 0.11639(18) 0.0167(6) Uani 1.00 1 d . . .
C(2) C -0.2826(3) 0.0066(2) 0.07785(18) 0.0175(6) Uani 1.00 1 d . . .
C(3) C -0.4094(3) -0.0030(2) 0.1098(2) 0.0221(7) Uani 1.00 1 d . . .
C(4) C -0.4311(3) 0.0469(2) 0.1817(2) 0.0234(7) Uani 1.00 1 d . . .
C(5) C -0.3267(3) 0.1064(2) 0.2207(2) 0.0223(7) Uani 1.00 1 d . . .
C(6) C -0.2000(3) 0.1175(2) 0.18864(19) 0.0189(7) Uani 1.00 1 d . . .
C(7) C -0.0963(3) 0.1895(2) 0.2318(2) 0.0226(7) Uani 1.00 1 d . . .
C(8) C 0.0822(3) 0.0764(2) 0.28645(18) 0.0200(7) Uani 1.00 1 d . . .
C(9) C 0.1726(3) 0.0034(2) 0.25039(18) 0.0175(6) Uani 1.00 1 d . . .
C(10) C 0.2612(3) -0.0529(2) 0.30747(19) 0.0202(7) Uani 1.00 1 d . . .
C(11) C 0.3385(3) -0.1255(2) 0.2790(2) 0.0219(7) Uani 1.00 1 d . . .
C(12) C 0.3269(3) -0.1430(2) 0.19195(19) 0.0204(7) Uani 1.00 1 d . . .
C(13) C 0.2393(2) -0.0870(2) 0.13410(18) 0.0182(6) Uani 1.00 1 d . . .
C(14) C 0.1618(2) -0.0134(2) 0.16221(18) 0.0164(6) Uani 1.00 1 d . . .
C(15) C 0.1535(3) 0.2409(2) 0.2592(2) 0.0250(7) Uani 1.00 1 d . . .
C(16) C 0.1265(3) 0.3196(2) 0.1921(2) 0.0371(10) Uani 1.00 1 d . . .
C(17) C 0.1400(4) 0.2815(2) 0.3477(2) 0.0398(10) Uani 1.00 1 d . . .
C(18) C 0.3040(3) 0.2058(2) 0.2584(2) 0.0316(9) Uani 1.00 1 d . . .
C(19) C 0.6163(4) 0.1766(2) 0.4851(2) 0.0354(9) Uani 1.00 1 d . . .
C(20) C 0.7610(4) 0.1940(2) 0.5007(2) 0.0412(10) Uani 1.00 1 d . . .
C(21) C 0.8580(4) 0.1290(3) 0.4808(2) 0.0475(12) Uani 1.00 1 d . . .
C(22) C 0.8124(4) 0.0443(3) 0.4450(2) 0.0455(11) Uani 1.00 1 d . . .
C(23) C 0.6692(4) 0.0253(2) 0.4291(2) 0.0421(11) Uani 1.00 1 d . . .
C(24) C 0.5731(4) 0.0904(2) 0.4483(2) 0.0343(9) Uani 1.00 1 d . . .
C(25) C 0.5107(5) 0.2472(3) 0.5059(2) 0.0514(12) Uani 1.00 1 d . . .
H(1) H -0.2684 -0.0282 0.0284 0.021 Uiso 1.00 1 c R . .
H(2) H -0.4808 -0.0438 0.0823 0.026 Uiso 1.00 1 c R . .
H(3) H -0.5172 0.0403 0.2043 0.029 Uiso 1.00 1 c R . .
H(4) H -0.3418 0.1406 0.2703 0.027 Uiso 1.00 1 c R . .
H(5) H -0.1135 0.1981 0.2891 0.027 Uiso 1.00 1 c R . .
H(6) H -0.1113 0.2471 0.2014 0.027 Uiso 1.00 1 c R . .
H(7) H 0.1296 0.0949 0.3412 0.024 Uiso 1.00 1 c R . .
H(8) H -0.0055 0.0480 0.2926 0.024 Uiso 1.00 1 c R . .
H(9) H 0.2689 -0.0412 0.3673 0.024 Uiso 1.00 1 c R . .
H(10) H 0.3988 -0.1630 0.3188 0.026 Uiso 1.00 1 c R . .
H(11) H 0.3786 -0.1930 0.1717 0.025 Uiso 1.00 1 c R . .
H(12) H 0.2322 -0.0992 0.0743 0.022 Uiso 1.00 1 c R . .
H(13) H 0.1973 0.3665 0.2043 0.044 Uiso 1.00 1 c R . .
H(14) H 0.1293 0.2944 0.1366 0.044 Uiso 1.00 1 c R . .
H(15) H 0.0362 0.3466 0.1939 0.044 Uiso 1.00 1 c R . .
H(16) H 0.0522 0.3134 0.3448 0.047 Uiso 1.00 1 c R . .
H(17) H 0.1443 0.2320 0.3884 0.047 Uiso 1.00 1 c R . .
H(18) H 0.2152 0.3243 0.3646 0.048 Uiso 1.00 1 c R . .
H(19) H 0.3317 0.1666 0.3068 0.038 Uiso 1.00 1 c R . .
H(20) H 0.3075 0.1709 0.2073 0.037 Uiso 1.00 1 c R . .
H(21) H 0.3664 0.2579 0.2604 0.038 Uiso 1.00 1 c R . .
H(22) H 0.7936 0.2521 0.5258 0.048 Uiso 1.00 1 c R . .
H(23) H 0.9561 0.1430 0.4917 0.056 Uiso 1.00 1 c R . .
H(24) H 0.8788 -0.0008 0.4315 0.056 Uiso 1.00 1 c R . .
H(25) H 0.6369 -0.0333 0.4048 0.051 Uiso 1.00 1 c R . .
H(26) H 0.4750 0.0766 0.4362 0.040 Uiso 1.00 1 c R . .
H(27) H 0.4654 0.2758 0.4545 0.060 Uiso 1.00 1 c R . .
H(28) H 0.4421 0.2168 0.5339 0.060 Uiso 1.00 1 c R . .
H(29) H 0.5578 0.2940 0.5426 0.060 Uiso 1.00 1 c R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Bi Bi -4.108 10.257
;
International Tables for Crystallography
(1992, 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
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
Bi(1) Bi(1) N(1) 152.31(4) yes 3_555 . .
Bi(1) Bi(1) C(1) 93.87(7) yes 3_555 . .
Bi(1) Bi(1) C(14) 92.18(7) yes 3_555 . .
N(1) Bi(1) C(1) 68.94(8) yes . . .
N(1) Bi(1) C(14) 69.48(8) yes . . .
C(1) Bi(1) C(14) 96.54(10) yes . . .
Bi(1) N(1) C(7) 99.02(16) yes . . .
Bi(1) N(1) C(8) 100.12(16) yes . . .
Bi(1) N(1) C(15) 119.46(18) yes . . .
C(7) N(1) C(8) 110.1(2) yes . . .
C(7) N(1) C(15) 112.5(2) yes . . .
C(8) N(1) C(15) 114.1(2) yes . . .
Bi(1) C(1) C(2) 121.5(2) yes . . .
Bi(1) C(1) C(6) 120.28(19) yes . . .
C(2) C(1) C(6) 118.2(2) yes . . .
C(1) C(2) C(3) 121.7(2) yes . . .
C(2) C(3) C(4) 119.7(2) yes . . .
C(3) C(4) C(5) 119.5(3) yes . . .
C(4) C(5) C(6) 121.4(2) yes . . .
C(1) C(6) C(5) 119.6(2) yes . . .
C(1) C(6) C(7) 122.8(2) yes . . .
C(5) C(6) C(7) 117.5(2) yes . . .
N(1) C(7) C(6) 113.1(2) yes . . .
N(1) C(8) C(9) 115.3(2) yes . . .
C(8) C(9) C(10) 118.6(2) yes . . .
C(8) C(9) C(14) 121.9(2) yes . . .
C(10) C(9) C(14) 119.3(2) yes . . .
C(9) C(10) C(11) 121.5(2) yes . . .
C(10) C(11) C(12) 119.3(2) yes . . .
C(11) C(12) C(13) 119.8(2) yes . . .
C(12) C(13) C(14) 121.2(2) yes . . .
Bi(1) C(14) C(9) 121.8(2) yes . . .
Bi(1) C(14) C(13) 119.33(19) yes . . .
C(9) C(14) C(13) 118.8(2) yes . . .
N(1) C(15) C(16) 109.5(2) yes . . .
N(1) C(15) C(17) 112.6(2) yes . . .
N(1) C(15) C(18) 108.7(2) yes . . .
C(16) C(15) C(17) 108.9(2) yes . . .
C(16) C(15) C(18) 107.0(2) yes . . .
C(17) C(15) C(18) 109.9(2) yes . . .
C(20) C(19) C(24) 117.0(3) yes . . .
C(20) C(19) C(25) 121.9(3) yes . . .
C(24) C(19) C(25) 121.0(3) yes . . .
C(19) C(20) C(21) 121.8(3) yes . . .
C(20) C(21) C(22) 119.9(4) yes . . .
C(21) C(22) C(23) 119.4(4) yes . . .
C(22) C(23) C(24) 120.5(3) yes . . .
C(19) C(24) C(23) 121.4(3) yes . . .
C(1) C(2) H(1) 119.2 no . . .
C(3) C(2) H(1) 119.2 no . . .
C(2) C(3) H(2) 120.1 no . . .
C(4) C(3) H(2) 120.1 no . . .
C(3) C(4) H(3) 120.2 no . . .
C(5) C(4) H(3) 120.3 no . . .
C(4) C(5) H(4) 119.3 no . . .
C(6) C(5) H(4) 119.3 no . . .
N(1) C(7) H(5) 108.5 no . . .
N(1) C(7) H(6) 108.6 no . . .
C(6) C(7) H(5) 108.6 no . . .
C(6) C(7) H(6) 108.6 no . . .
H(5) C(7) H(6) 109.5 no . . .
N(1) C(8) H(7) 108.0 no . . .
N(1) C(8) H(8) 108.0 no . . .
C(9) C(8) H(7) 108.0 no . . .
C(9) C(8) H(8) 108.0 no . . .
H(7) C(8) H(8) 109.5 no . . .
C(9) C(10) H(9) 119.3 no . . .
C(11) C(10) H(9) 119.2 no . . .
C(10) C(11) H(10) 120.4 no . . .
C(12) C(11) H(10) 120.3 no . . .
C(11) C(12) H(11) 120.1 no . . .
C(13) C(12) H(11) 120.1 no . . .
C(12) C(13) H(12) 119.4 no . . .
C(14) C(13) H(12) 119.4 no . . .
C(15) C(16) H(13) 109.5 no . . .
C(15) C(16) H(14) 109.5 no . . .
C(15) C(16) H(15) 109.4 no . . .
H(13) C(16) H(14) 109.5 no . . .
H(13) C(16) H(15) 109.5 no . . .
H(14) C(16) H(15) 109.5 no . . .
C(15) C(17) H(16) 109.4 no . . .
C(15) C(17) H(17) 109.6 no . . .
C(15) C(17) H(18) 109.5 no . . .
H(16) C(17) H(17) 109.5 no . . .
H(16) C(17) H(18) 109.5 no . . .
H(17) C(17) H(18) 109.5 no . . .
C(15) C(18) H(19) 109.5 no . . .
C(15) C(18) H(20) 109.5 no . . .
C(15) C(18) H(21) 109.4 no . . .
H(19) C(18) H(20) 109.5 no . . .
H(19) C(18) H(21) 109.5 no . . .
H(20) C(18) H(21) 109.5 no . . .
C(19) C(20) H(22) 118.9 no . . .
C(21) C(20) H(22) 119.3 no . . .
C(20) C(21) H(23) 120.0 no . . .
C(22) C(21) H(23) 120.1 no . . .
C(21) C(22) H(24) 120.3 no . . .
C(23) C(22) H(24) 120.3 no . . .
C(22) C(23) H(25) 119.9 no . . .
C(24) C(23) H(25) 119.6 no . . .
C(19) C(24) H(26) 119.1 no . . .
C(23) C(24) H(26) 119.5 no . . .
C(19) C(25) H(27) 109.7 no . . .
C(19) C(25) H(28) 109.5 no . . .
C(19) C(25) H(29) 109.3 no . . .
H(27) C(25) H(28) 109.5 no . . .
H(27) C(25) H(29) 109.5 no . . .
H(28) C(25) H(29) 109.5 no . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Bi(1) Bi(1) 3.0648(2) yes . 3_555
Bi(1) N(1) 2.894(2) yes . .
Bi(1) C(1) 2.279(2) yes . .
Bi(1) C(14) 2.272(2) yes . .
N(1) C(7) 1.472(3) yes . .
N(1) C(8) 1.469(3) yes . .
N(1) C(15) 1.504(3) yes . .
C(1) C(2) 1.391(3) yes . .
C(1) C(6) 1.404(4) yes . .
C(2) C(3) 1.389(4) yes . .
C(3) C(4) 1.380(4) yes . .
C(4) C(5) 1.381(4) yes . .
C(5) C(6) 1.391(4) yes . .
C(6) C(7) 1.513(4) yes . .
C(8) C(9) 1.516(4) yes . .
C(9) C(10) 1.393(3) yes . .
C(9) C(14) 1.399(4) yes . .
C(10) C(11) 1.384(4) yes . .
C(11) C(12) 1.382(4) yes . .
C(12) C(13) 1.392(3) yes . .
C(13) C(14) 1.394(4) yes . .
C(15) C(16) 1.535(4) yes . .
C(15) C(17) 1.532(5) yes . .
C(15) C(18) 1.527(4) yes . .
C(19) C(20) 1.391(5) yes . .
C(19) C(24) 1.393(5) yes . .
C(19) C(25) 1.496(6) yes . .
C(20) C(21) 1.379(6) yes . .
C(21) C(22) 1.374(6) yes . .
C(22) C(23) 1.382(6) yes . .
C(23) C(24) 1.371(5) yes . .
C(2) H(1) 0.950 no . .
C(3) H(2) 0.950 no . .
C(4) H(3) 0.950 no . .
C(5) H(4) 0.950 no . .
C(7) H(5) 0.950 no . .
C(7) H(6) 0.950 no . .
C(8) H(7) 0.950 no . .
C(8) H(8) 0.950 no . .
C(10) H(9) 0.950 no . .
C(11) H(10) 0.950 no . .
C(12) H(11) 0.950 no . .
C(13) H(12) 0.950 no . .
C(16) H(13) 0.950 no . .
C(16) H(14) 0.950 no . .
C(16) H(15) 0.950 no . .
C(17) H(16) 0.950 no . .
C(17) H(17) 0.950 no . .
C(17) H(18) 0.950 no . .
C(18) H(19) 0.950 no . .
C(18) H(20) 0.950 no . .
C(18) H(21) 0.950 no . .
C(20) H(22) 0.950 no . .
C(21) H(23) 0.950 no . .
C(22) H(24) 0.950 no . .
C(23) H(25) 0.950 no . .
C(24) H(26) 0.950 no . .
C(25) H(27) 0.950 no . .
C(25) H(28) 0.950 no . .
C(25) H(29) 0.950 no . .
