##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(N,N-Dimethylformamide-κO)bis(3-hydroxypicolinato-
κ²N,O²)phenylbismuth(III)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H20 Bi N3 O7'
_chemical_formula_sum     'C21 H20 Bi N3 O7'
_chemical_formula_iupac     '[Bi (C6 H5) (C6 H4 N O3)2 (C3 H7 N O)]'
_chemical_formula_weight     635.38
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     8.2377(16)
_cell_length_b     21.989(4)
_cell_length_c     12.380(3)
_cell_angle_alpha     90.00
_cell_angle_beta     104.24(3)
_cell_angle_gamma     90.00
_cell_volume     2173.6(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7774
_cell_measurement_theta_min     2.51
_cell_measurement_theta_max     24.71
_cell_measurement_temperature     294.0(10)
_exptl_crystal_description     block
_exptl_crystal_colour     light-yellow
_exptl_crystal_size_max     0.14
_exptl_crystal_size_mid     0.11
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.942
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1224
_exptl_absorpt_coefficient_mu     8.160
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2004)'
_exptl_absorpt_correction_T_min     0.356
_exptl_absorpt_correction_T_max     0.450
_exptl_special_details
;
;
_diffrn_ambient_temperature     294.0(10)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1000 CCD'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     15126
_diffrn_reflns_av_R_equivalents     0.0307
_diffrn_reflns_av_sigmaI/netI     0.0248
_diffrn_reflns_theta_min     1.93
_diffrn_reflns_theta_max     24.81
_diffrn_reflns_theta_full     24.81
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -25
_diffrn_reflns_limit_k_max     25
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     3669
_reflns_number_gt     3314
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0245
_refine_ls_R_factor_gt     0.0207
_refine_ls_wR_factor_gt     0.0468
_refine_ls_wR_factor_ref     0.0481
_refine_ls_goodness_of_fit_ref     1.108
_refine_ls_restrained_S_all     1.108
_refine_ls_number_reflns     3669
_refine_ls_number_parameters     299
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0202P)²+1.6444P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.719
_refine_diff_density_min     -0.942
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 2004)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction     'SAINT-Plus and XPREP (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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_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_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)
data_global
_journal_date_recd_electronic     2010-10-20
_journal_date_accepted     2010-10-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     12
_journal_page_first     m1547
_journal_page_last     m1548
_journal_paper_category     QM
_journal_coeditor_code     SJ5046
_publ_contact_author_name     'Kenton H. Whitmire'
_publ_contact_author_address
;
Rice University, Houston, TX 77005, USA
;
_publ_contact_author_email     whitmir@rice.edu
_publ_contact_author_fax     713-348-5155
_publ_contact_author_phone     713-348-5650
_publ_section_title
;\
(N,N-Dimethylformamide-κO)bis(3-hydroxypicolinato-\
κ²N,O²)phenylbismuth(III)
;
loop_
    _publ_author_name
    _publ_author_address
    'Stavila, Vitalie'
;
Department of Chemistry
Rice University
6100 Main Street
Houston, Texas 77005, USA
;
    'Whitmire, Kenton H.'
;
Department of Chemistry
Rice University
6100 Main Street
Houston, Texas 77005, USA
;
