#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:05:58 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179879 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/75/7017589.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_7017589
loop_
_publ_author_name
'Anjaneyulu, O.'
'Maddileti, D.'
'Kumara Swamy, K. C.'
_publ_section_title
;
 Structural motifs in phenylbismuth heterocyclic carboxylates--secondary
 interactions leading to oligomers.
;
_journal_issue                   3
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1004
_journal_page_last               1012
_journal_paper_doi               10.1039/c1dt11207d
_journal_volume                  41
_journal_year                    2012
_chemical_formula_sum            'C17 H13 Bi O3'
_chemical_formula_weight         474.25
_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                 101.02(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.340(2)
_cell_length_b                   9.7251(19)
_cell_length_c                   15.679(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1547.6(5)
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  '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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14384
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    11.399
_exptl_absorpt_correction_T_max  0.3416
_exptl_absorpt_correction_T_min  0.1628
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.035
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0191
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0240P)²+1.0448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0465
_refine_ls_wR_factor_ref         0.0471
_reflns_number_gt                2523
_reflns_number_total             2726
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt11207d.txt
_cod_data_source_block           compound10
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7017589
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
Bi Bi 0.290643(12) 0.533586(13) 0.213906(8) 0.03269(7) Uani 1 1 d .
O1 O 0.1612(2) 0.7464(2) 0.22107(17) 0.0371(6) Uani 1 1 d .
O2 O 0.0319(2) 0.8788(2) 0.28373(16) 0.0372(6) Uani 1 1 d .
C15 C -0.1855(4) 0.6798(5) 0.2244(3) 0.0493(10) Uani 1 1 d .
H15 H -0.2262 0.7468 0.2525 0.059 Uiso 1 1 calc R
C1 C 0.3984(3) 0.6659(4) 0.1341(2) 0.0336(8) Uani 1 1 d .
C2 C 0.4580(4) 0.7886(4) 0.1645(3) 0.0468(10) Uani 1 1 d .
H2 H 0.4535 0.8186 0.2202 0.056 Uiso 1 1 calc R
C3 C 0.5241(5) 0.8671(5) 0.1130(3) 0.0622(13) Uani 1 1 d .
H3 H 0.5648 0.9486 0.1345 0.075 Uiso 1 1 calc R
C4 C 0.5297(5) 0.8247(6) 0.0303(4) 0.0696(15) Uani 1 1 d .
H4 H 0.5751 0.8770 -0.0040 0.084 Uiso 1 1 calc R
C5 C 0.4687(5) 0.7055(5) -0.0018(3) 0.0621(13) Uani 1 1 d .
H5 H 0.4714 0.6777 -0.0582 0.075 Uiso 1 1 calc R
C6 C 0.4029(4) 0.6264(5) 0.0496(3) 0.0484(10) Uani 1 1 d .
H6 H 0.3612 0.5458 0.0273 0.058 Uiso 1 1 calc R
C7 C 0.4037(4) 0.6095(4) 0.3417(2) 0.0391(8) Uani 1 1 d .
C8 C 0.3395(5) 0.6702(5) 0.4005(3) 0.0605(12) Uani 1 1 d .
H8 H 0.2485 0.6800 0.3870 0.073 Uiso 1 1 calc R
C9 C 0.4080(7) 0.7172(7) 0.4798(3) 0.0849(18) Uani 1 1 d .
H9 H 0.3628 0.7584 0.5189 0.102 Uiso 1 1 calc R
C10 C 0.5410(7) 0.7034(6) 0.5004(3) 0.0770(16) Uani 1 1 d .
H10 H 0.5872 0.7361 0.5533 0.092 Uiso 1 1 calc R
C11 C 0.6060(5) 0.6416(5) 0.4435(3) 0.0659(14) Uani 1 1 d .
H11 H 0.6969 0.6305 0.4581 0.079 Uiso 1 1 calc R
C12 C 0.5386(4) 0.5946(5) 0.3637(3) 0.0516(10) Uani 1 1 d .
H12 H 0.5844 0.5531 0.3250 0.062 Uiso 1 1 calc R
C13 C 0.0527(3) 0.7714(3) 0.2424(2) 0.0292(7) Uani 1 1 d .
C14 C -0.0587(3) 0.6770(4) 0.2170(2) 0.0324(8) Uani 1 1 d .
C16 C -0.1521(4) 0.4944(4) 0.1520(3) 0.0523(12) Uani 1 1 d .
H16 H -0.1645 0.4119 0.1216 0.063 Uiso 1 1 calc R
O3 O -0.0350(3) 0.5621(3) 0.17218(19) 0.0448(7) Uani 1 1 d .
C17 C -0.2459(4) 0.5616(5) 0.1814(3) 0.0556(12) Uani 1 1 d .
H17 H -0.3339 0.5361 0.1751 0.067 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 Bi C7 94.60(13) . .
C1 Bi O2 84.68(11) . 2_545
C7 Bi O2 85.71(12) . 2_545
C1 Bi O1 82.86(10) . .
C7 Bi O1 83.02(12) . .
O2 Bi O1 162.45(8) 2_545 .
C13 O1 Bi 133.8(2) . .
C13 O2 Bi 109.0(2) . 2
C14 C15 C17 107.0(4) . .
C14 C15 H15 126.5 . .
C17 C15 H15 126.5 . .
C2 C1 C6 118.2(4) . .
C2 C1 Bi 122.7(3) . .
C6 C1 Bi 119.1(3) . .
C3 C2 C1 120.8(4) . .
C3 C2 H2 119.6 . .
C1 C2 H2 119.6 . .
C4 C3 C2 120.0(5) . .
C4 C3 H3 120.0 . .
C2 C3 H3 120.0 . .
C5 C4 C3 120.1(5) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C4 C5 C6 120.0(4) . .
C4 C5 H5 120.0 . .
C6 C5 H5 120.0 . .
C5 C6 C1 120.8(4) . .
C5 C6 H6 119.6 . .
C1 C6 H6 119.6 . .
C8 C7 C12 118.3(4) . .
C8 C7 Bi 120.5(3) . .
C12 C7 Bi 121.2(3) . .
C7 C8 C9 121.1(5) . .
C7 C8 H8 119.4 . .
C9 C8 H8 119.4 . .
C10 C9 C8 120.1(5) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C11 C10 C9 119.6(5) . .
C11 C10 H10 120.2 . .
C9 C10 H10 120.2 . .
C10 C11 C12 120.8(5) . .
C10 C11 H11 119.6 . .
C12 C11 H11 119.6 . .
C7 C12 C11 120.0(5) . .
C7 C12 H12 120.0 . .
C11 C12 H12 120.0 . .
O1 C13 O2 122.9(3) . .
O1 C13 C14 120.2(3) . .
O2 C13 C14 116.9(3) . .
C15 C14 O3 109.7(3) . .
C15 C14 C13 134.0(4) . .
O3 C14 C13 116.2(3) . .
C17 C16 O3 111.1(4) . .
C17 C16 H16 124.5 . .
O3 C16 H16 124.5 . .
C16 O3 C14 106.0(3) . .
C16 C17 C15 106.3(4) . .
C16 C17 H17 126.9 . .
C15 C17 H17 126.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi C1 2.235(4) .
Bi C7 2.243(4) .
Bi O2 2.368(2) 2_545
Bi O1 2.479(2) .
O1 C13 1.254(4) .
O2 C13 1.269(4) .
O2 Bi 2.368(2) 2
C15 C14 1.338(5) .
C15 C17 1.417(6) .
C15 H15 0.9300 .
C1 C2 1.385(5) .
C1 C6 1.390(5) .
C2 C3 1.383(6) .
C2 H2 0.9300 .
C3 C4 1.373(7) .
C3 H3 0.9300 .
C4 C5 1.369(8) .
C4 H4 0.9300 .
C5 C6 1.383(6) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.368(6) .
C7 C12 1.379(6) .
C8 C9 1.385(7) .
C8 H8 0.9300 .
C9 C10 1.358(9) .
C9 H9 0.9300 .
C10 C11 1.357(8) .
C10 H10 0.9300 .
C11 C12 1.388(6) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.468(5) .
C14 O3 1.367(4) .
C16 C17 1.323(7) .
C16 O3 1.360(5) .
C16 H16 0.9300 .
C17 H17 0.9300 .
