#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/85/2228559.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_2228559
loop_
_publ_author_name
'Stavila, Vitalie'
'Whitmire, Kenton H.'
_publ_section_title
;
 (N,N-Dimethylformamide-κO)bis(3-hydroxypicolinato-κ²N,O²)phenylbismuth(III)
;
_journal_coeditor_code           SJ5046
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1547
_journal_page_last               m1548
_journal_paper_doi               10.1107/S1600536810044235
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Bi (C6 H5) (C6 H4 N O3)2 (C3 H7 N O)]'
_chemical_formula_moiety         'C21 H20 Bi N3 O7'
_chemical_formula_sum            'C21 H20 Bi N3 O7'
_chemical_formula_weight         635.38
_chemical_name_systematic
;
(N,N-Dimethylformamide-κO)bis(3-hydroxypicolinato-
κ²N,O²)phenylbismuth(III)
;
_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                 104.24(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2377(16)
_cell_length_b                   21.989(4)
_cell_length_c                   12.380(3)
_cell_measurement_reflns_used    7774
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      24.71
_cell_measurement_theta_min      2.51
_cell_volume                     2173.6(8)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.0(10)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       '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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15126
_diffrn_reflns_theta_full        24.81
_diffrn_reflns_theta_max         24.81
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.160
_exptl_absorpt_correction_T_max  0.450
_exptl_absorpt_correction_T_min  0.356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.942
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.942
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3669
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0207
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0202P)²+1.6444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0468
_refine_ls_wR_factor_ref         0.0481
_reflns_number_gt                3314
_reflns_number_total             3669
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5046.cif
_cod_data_source_block           I
_cod_original_cell_volume        2173.6(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228559
_cod_database_fobs_code          2228559
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi Bi1 0.163597(16) 0.410112(6) 0.270490(11) 0.02944(6) Uani d . 1 . .
N N1 -0.0947(4) 0.39564(14) 0.0950(3) 0.0350(7) Uani d . 1 . .
N N2 0.4598(3) 0.44505(13) 0.3132(2) 0.0296(7) Uani d . 1 . .
N N3 -0.1613(4) 0.30791(16) 0.4752(3) 0.0484(9) Uani d . 1 . .
O O11 0.2210(3) 0.43021(14) 0.0973(2) 0.0460(7) Uani d . 1 . .
O O12 0.1580(4) 0.43682(17) -0.0856(2) 0.0616(9) Uani d D 1 . .
O O13 -0.1422(4) 0.42463(17) -0.1993(3) 0.0700(10) Uani d D 1 . .
H H13A -0.047(2) 0.4405(17) -0.179(3) 0.084 Uiso d D 1 . .
O O21 0.3075(3) 0.39088(11) 0.4591(2) 0.0345(6) Uani d . 1 . .
O O22 0.5381(3) 0.40081(12) 0.5967(2) 0.0431(7) Uani d D 1 . .
O O23 0.7918(3) 0.45888(13) 0.5663(2) 0.0424(7) Uani d D 1 . .
H H23A 0.721(3) 0.4455(17) 0.599(2) 0.051 Uiso d D 1 . .
O O31 -0.0596(3) 0.35957(13) 0.3485(2) 0.0463(7) Uani d . 1 . .
C C11 0.1176(5) 0.42747(18) 0.0033(3) 0.0384(9) Uani d . 1 . .
C C12 -0.0582(5) 0.41051(16) -0.0012(3) 0.0342(8) Uani d . 1 . .
C C13 -0.1795(6) 0.41097(19) -0.1030(4) 0.0483(11) Uani d . 1 . .
C C14 -0.3443(6) 0.3973(2) -0.1012(4) 0.0602(13) Uani d . 1 . .
H H14A -0.4287 0.3973 -0.1668 0.072 Uiso calc R 1 . .
C C15 -0.3797(5) 0.3840(2) -0.0021(4) 0.0568(12) Uani d . 1 . .
H H15A -0.4893 0.3757 0.0007 0.068 Uiso calc R 1 . .
C C16 -0.2524(5) 0.3828(2) 0.0945(4) 0.0446(10) Uani d . 1 . .
H H16A -0.2781 0.3727 0.1614 0.053 Uiso calc R 1 . .
C C21 0.4577(5) 0.40784(15) 0.4986(3) 0.0311(8) Uani d . 1 . .
C C22 0.5437(4) 0.43992(15) 0.4213(3) 0.0279(8) Uani d . 1 . .
C C23 0.7050(4) 0.46376(16) 0.4596(3) 0.0310(8) Uani d . 1 . .
C C24 0.7768(4) 0.49391(17) 0.3847(3) 0.0372(9) Uani d . 1 . .
H H24A 0.8836 0.5105 0.4082 0.045 Uiso calc R 1 . .
C C25 0.6894(5) 0.49916(19) 0.2758(3) 0.0405(10) Uani d . 1 . .
H H25A 0.7360 0.5194 0.2247 0.049 Uiso calc R 1 . .
C C26 0.5304(5) 0.47394(18) 0.2424(3) 0.0381(9) Uani d . 1 . .
H H26A 0.4716 0.4774 0.1682 0.046 Uiso calc R 1 . .
C C31 -0.0559(5) 0.34549(19) 0.4457(4) 0.0421(10) Uani d . 1 . .
H H31A 0.024(5) 0.3600(19) 0.512(4) 0.056(13) Uiso d . 1 . .
C C32 -0.1501(7) 0.2935(3) 0.5913(4) 0.0744(16) Uani d . 1 . .
H H32A -0.0565 0.3146 0.6378 0.112 Uiso calc R 1 . .
H H32B -0.1352 0.2505 0.6026 0.112 Uiso calc R 1 . .
H H32C -0.2513 0.3060 0.6104 0.112 Uiso calc R 1 . .
C C33 -0.2927(7) 0.2800(3) 0.3906(5) 0.0903(19) Uani d . 1 . .
H H33A -0.2842 0.2932 0.3183 0.135 Uiso calc R 1 . .
H H33B -0.3997 0.2916 0.4017 0.135 Uiso calc R 1 . .
H H33C -0.2814 0.2365 0.3955 0.135 Uiso calc R 1 . .
C C41 0.2374(4) 0.31401(17) 0.2439(3) 0.0341(8) Uani d . 1 . .
C C42 0.2978(6) 0.2968(2) 0.1537(4) 0.0550(12) Uani d . 1 . .
H H42A 0.3107 0.3258 0.1019 0.066 Uiso calc R 1 . .
C C43 0.3391(6) 0.2369(3) 0.1397(4) 0.0666(14) Uani d . 1 . .
H H43A 0.3812 0.2263 0.0791 0.080 Uiso calc R 1 . .
C C44 0.3194(6) 0.1938(3) 0.2124(4) 0.0676(16) Uani d . 1 . .
H H44A 0.3451 0.1535 0.2011 0.081 Uiso calc R 1 . .
C C45 0.2610(6) 0.2096(2) 0.3034(4) 0.0602(13) Uani d . 1 . .
H H45A 0.2486 0.1800 0.3545 0.072 Uiso calc R 1 . .
C C46 0.2204(5) 0.26970(18) 0.3191(4) 0.0453(10) Uani d . 1 . .
H H46A 0.1814 0.2802 0.3810 0.054 Uiso calc R 1 . .
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'
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'
Bi Bi -4.1077 10.2566 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C41 Bi1 O11 . . 85.44(12) ?
C41 Bi1 O21 . . 83.65(11) ?
O11 Bi1 O21 . . 139.90(9) ?
C41 Bi1 N2 . . 92.01(11) ?
O11 Bi1 N2 . . 74.25(9) ?
O21 Bi1 N2 . . 67.72(9) ?
C41 Bi1 O31 . . 83.76(12) ?
O11 Bi1 O31 . . 139.33(9) ?
O21 Bi1 O31 . . 77.37(9) ?
N2 Bi1 O31 . . 145.09(9) ?
C41 Bi1 N1 . . 87.62(11) ?
O11 Bi1 N1 . . 64.98(10) ?
O21 Bi1 N1 . . 152.21(9) ?
N2 Bi1 N1 . . 139.13(10) ?
O31 Bi1 N1 . . 75.49(10) ?
C16 N1 C12 . . 118.8(3) ?
C16 N1 Bi1 . . 127.9(3) ?
C12 N1 Bi1 . . 112.8(2) ?
C26 N2 C22 . . 119.6(3) ?
C26 N2 Bi1 . . 125.0(2) ?
C22 N2 Bi1 . . 114.9(2) ?
C31 N3 C33 . . 119.6(4) ?
C31 N3 C32 . . 121.8(4) ?
C33 N3 C32 . . 118.6(4) ?
C11 O11 Bi1 . . 126.2(2) ?
C21 O21 Bi1 . . 121.9(2) ?
C31 O31 Bi1 . . 129.4(3) ?
O12 C11 O11 . . 122.8(4) ?
O12 C11 C12 . . 118.7(3) ?
O11 C11 C12 . . 118.5(3) ?
N1 C12 C13 . . 122.4(4) ?
N1 C12 C11 . . 117.3(3) ?
C13 C12 C11 . . 120.3(4) ?
O13 C13 C14 . . 120.1(4) ?
O13 C13 C12 . . 122.3(4) ?
C14 C13 C12 . . 117.7(4) ?
C15 C14 C13 . . 119.1(4) ?
C14 C15 C16 . . 119.9(4) ?
N1 C16 C15 . . 122.1(4) ?
O22 C21 O21 . . 125.1(3) ?
O22 C21 C22 . . 117.4(3) ?
O21 C21 C22 . . 117.5(3) ?
N2 C22 C23 . . 121.1(3) ?
N2 C22 C21 . . 117.7(3) ?
C23 C22 C21 . . 121.3(3) ?
O23 C23 C24 . . 119.0(3) ?
O23 C23 C22 . . 122.4(3) ?
C24 C23 C22 . . 118.6(3) ?
C25 C24 C23 . . 119.5(3) ?
C24 C25 C26 . . 119.3(3) ?
N2 C26 C25 . . 121.9(3) ?
O31 C31 N3 . . 124.7(4) ?
C46 C41 C42 . . 117.9(4) ?
C46 C41 Bi1 . . 119.3(3) ?
C42 C41 Bi1 . . 122.7(3) ?
C43 C42 C41 . . 120.8(5) ?
C44 C43 C42 . . 120.9(5) ?
C43 C44 C45 . . 119.7(5) ?
C44 C45 C46 . . 120.0(5) ?
C41 C46 C45 . . 120.7(4) ?
O13 H13A O12 . . 147(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Bi1 C41 . 2.245(4) ?
Bi1 O11 . 2.348(3) ?
Bi1 O21 . 2.382(3) ?
Bi1 N2 . 2.488(3) ?
Bi1 O31 . 2.534(3) ?
Bi1 N1 . 2.660(3) ?
N1 C16 . 1.328(5) ?
N1 C12 . 1.338(5) ?
N2 C26 . 1.327(4) ?
N2 C22 . 1.352(4) ?
N3 C31 . 1.313(5) ?
N3 C33 . 1.445(6) ?
N3 C32 . 1.453(6) ?
O11 C11 . 1.264(5) ?
O12 C11 . 1.243(5) ?
O13 C13 . 1.336(5) ?
O21 C21 . 1.269(4) ?
O22 C21 . 1.242(5) ?
O23 C23 . 1.342(4) ?
O31 C31 . 1.235(5) ?
C11 C12 . 1.483(5) ?
C12 C13 . 1.403(6) ?
C13 C14 . 1.396(7) ?
C14 C15 . 1.360(7) ?
C15 C16 . 1.384(6) ?
C21 C22 . 1.499(5) ?
C22 C23 . 1.398(5) ?
C23 C24 . 1.386(5) ?
C24 C25 . 1.368(5) ?
C25 C26 . 1.388(5) ?
C41 C46 . 1.378(6) ?
C41 C42 . 1.382(5) ?
C42 C43 . 1.381(7) ?
C43 C44 . 1.345(7) ?
C44 C45 . 1.374(7) ?
C45 C46 . 1.389(6) ?
O13 H13A . 0.84(3) ?
O23 H23A . 0.84(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O13 H13A O12 . 0.84(3) 1.80(3) 2.541(5) 147(4)
O23 H23A O22 . 0.84(3) 1.79(3) 2.555(5) 150(3)
O23 H23A O13 1_656 0.84(3) 2.52(2) 2.917(6) 110(2)
