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#$Date: 2017-04-05 12:56:39 +0300 (Wed, 05 Apr 2017) $
#$Revision: 195126 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/21/7042119.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_7042119
loop_
_publ_author_name
'Toma, Ana Maria'
'Pop, Alexandra'
'Silvestru, Anca'
'Rüffer, Tobias'
'Lang, Heinrich'
'Mehring, Michael'
_publ_section_title
;
 Bismuthπ arene versus bismuthhalide coordination in heterocyclic
 diorganobismuth(iii) compounds with transannular N→ Bi
 interaction.
;
_journal_issue                   12
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3953
_journal_page_last               3962
_journal_paper_doi               10.1039/c7dt00188f
_journal_volume                  46
_journal_year                    2017
_chemical_formula_moiety         'C17 H19 Bi F N O'
_chemical_formula_sum            'C17 H19 Bi F N O'
_chemical_formula_weight         481.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-02-14 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.129(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.506(7)
_cell_length_b                   8.658(5)
_cell_length_c                   18.119(12)
_cell_measurement_reflns_used    4634
_cell_measurement_temperature    297
_cell_measurement_theta_max      20.90
_cell_measurement_theta_min      2.39
_cell_volume                     1842.0(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;Brandenburg, K. [or Brandenburg, K. & Putz, H., or Brandenburg, K. & Berndt,
 M.] (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
;
_computing_publication_material
; Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004).
 J. Appl. Cryst. 37, 335-338.
;
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      297
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17537
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.394
_exptl_absorpt_coefficient_mu    9.579
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.447766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; SADABS - V2.03 (Bruker 2001)was used for absorption 
correction. R(int) =  0.1461 before parameter refinement
 and  0.0619 after parameter refinement. Ratio of minimum 
to maximum apparent transmission:  0.447766
 Lambda/2 correction factor = 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.988
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0296P)²+1.5568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2761
_reflns_number_total             3425
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt00188f2.cif
_cod_data_source_block           platon_sq
_cod_depositor_comments
'Adding full bibliography for 7042110--7042119.cif.'
_cod_database_code               7042119
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Bi1 Bi 0.66483(2) 0.08456(3) 0.27982(2) 0.03784(11) Uani 1 1 d . .
C1 C 0.7720(6) 0.1853(9) 0.3953(4) 0.0374(17) Uani 1 1 d . .
C6 C 0.8207(6) 0.0887(9) 0.4582(4) 0.0435(18) Uani 1 1 d . .
C5 C 0.8918(7) 0.1469(10) 0.5285(5) 0.058(2) Uani 1 1 d . .
H5 H 0.9235 0.0800 0.5705 0.069 Uiso 1 1 calc R U
C4 C 0.9170(7) 0.2997(10) 0.5381(5) 0.059(2) Uani 1 1 d . .
H4 H 0.9665 0.3368 0.5858 0.071 Uiso 1 1 calc R U
C3 C 0.8684(7) 0.3988(10) 0.4764(5) 0.053(2) Uani 1 1 d . .
H3 H 0.8831 0.5041 0.4827 0.063 Uiso 1 1 calc R U
C2 C 0.7973(6) 0.3418(9) 0.4046(4) 0.0412(18) Uani 1 1 d . .
H2 H 0.7664 0.4088 0.3625 0.049 Uiso 1 1 calc R U
C7 C 0.8007(7) -0.0831(9) 0.4479(5) 0.057(2) Uani 1 1 d . .
H7A H 0.8584 -0.1289 0.4301 0.068 Uiso 1 1 calc R U
H7B H 0.8072 -0.1293 0.4980 0.068 Uiso 1 1 calc R U
C14 C 0.5005(6) 0.0813(9) 0.3024(4) 0.0411(18) Uani 1 1 d . .
C9 C 0.4903(6) -0.0089(9) 0.3634(4) 0.0401(19) Uani 1 1 d . .
C10 C 0.3864(7) -0.0340(10) 0.3711(5) 0.054(2) Uani 1 1 d . .
H10 H 0.3807 -0.0972 0.4111 0.064 Uiso 1 1 calc R U
C11 C 0.2896(9) 0.0355(12) 0.3188(7) 0.080(3) Uani 1 1 d . .
H11 H 0.2186 0.0168 0.3228 0.096 Uiso 1 1 calc R U
C12 C 0.2993(8) 0.1324(12) 0.2608(7) 0.073(3) Uani 1 1 d . .
H12 H 0.2354 0.1837 0.2278 0.088 Uiso 1 1 calc R U
C13 C 0.4027(7) 0.1532(10) 0.2518(5) 0.054(2) Uani 1 1 d . .
H13 H 0.4079 0.2160 0.2115 0.065 Uiso 1 1 calc R U
C8 C 0.5964(7) -0.0734(8) 0.4230(4) 0.046(2) Uani 1 1 d . .
H8A H 0.6277 0.0026 0.4641 0.055 Uiso 1 1 calc R U
H8B H 0.5765 -0.1641 0.4469 0.055 Uiso 1 1 calc R U
C15 C 0.6772(7) -0.2798(8) 0.3668(5) 0.053(2) Uani 1 1 d . .
H15A H 0.6785 -0.3421 0.4116 0.063 Uiso 1 1 calc R U
H15B H 0.7435 -0.3071 0.3534 0.063 Uiso 1 1 calc R U
C16 C 0.5721(8) -0.3176(9) 0.2987(5) 0.056(2) Uani 1 1 d . .
H16A H 0.5693 -0.4276 0.2880 0.067 Uiso 1 1 calc R U
H16B H 0.5050 -0.2900 0.3111 0.067 Uiso 1 1 calc R U
C17 C 0.4730(8) -0.2523(14) 0.1667(5) 0.094(4) Uani 1 1 d . .
H17A H 0.4824 -0.2020 0.1221 0.141 Uiso 1 1 calc R U
H17B H 0.4103 -0.2065 0.1778 0.141 Uiso 1 1 calc R U
H17C H 0.4581 -0.3601 0.1554 0.141 Uiso 1 1 calc R U
F1 F 0.6199(4) 0.3158(5) 0.2261(2) 0.0516(11) Uani 1 1 d . .
N1 N 0.6850(5) -0.1162(6) 0.3893(3) 0.0390(15) Uani 1 1 d . .
O1 O 0.5737(5) -0.2353(7) 0.2327(3) 0.0616(16) Uani 1 1 d . .
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'
F F 0.0171 0.0103 '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
F1 Bi1 C14 88.9(2)
F1 Bi1 C1 92.2(2)
C14 Bi1 C1 97.3(3)
F1 Bi1 N1 152.82(17)
C14 Bi1 N1 72.8(2)
C1 Bi1 N1 71.1(2)
C6 C1 C2 118.4(7)
C6 C1 Bi1 119.3(5)
C2 C1 Bi1 122.2(5)
C5 C6 C1 120.4(8)
C5 C6 C7 120.2(7)
C1 C6 C7 119.3(7)
C4 C5 C6 121.6(8)
C4 C5 H5 119.2
C6 C5 H5 119.2
C5 C4 C3 119.1(8)
C5 C4 H4 120.5
C3 C4 H4 120.5
C4 C3 C2 120.1(8)
C4 C3 H3 119.9
C2 C3 H3 120.0
C1 C2 C3 120.4(8)
C1 C2 H2 119.8
C3 C2 H2 119.8
N1 C7 C6 110.8(6)
N1 C7 H7A 109.5
C6 C7 H7A 109.5
N1 C7 H7B 109.5
C6 C7 H7B 109.5
H7A C7 H7B 108.1
C9 C14 C13 118.1(7)
C9 C14 Bi1 119.6(5)
C13 C14 Bi1 121.9(6)
C10 C9 C14 121.2(8)
C10 C9 C8 120.1(8)
C14 C9 C8 118.6(7)
C9 C10 C11 119.6(8)
C9 C10 H10 120.2
C11 C10 H10 120.2
C12 C11 C10 119.8(9)
C12 C11 H11 120.1
C10 C11 H11 120.1
C13 C12 C11 120.3(9)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C14 120.8(9)
C12 C13 H13 119.6
C14 C13 H13 119.6
N1 C8 C9 113.4(6)
N1 C8 H8A 108.9
C9 C8 H8A 108.9
N1 C8 H8B 108.9
C9 C8 H8B 108.9
H8A C8 H8B 107.7
N1 C15 C16 113.3(7)
N1 C15 H15A 108.9
C16 C15 H15A 108.9
N1 C15 H15B 108.9
C16 C15 H15B 108.9
H15A C15 H15B 107.7
O1 C16 C15 109.0(7)
O1 C16 H16A 109.9
C15 C16 H16A 109.9
O1 C16 H16B 109.9
C15 C16 H16B 109.9
H16A C16 H16B 108.3
O1 C17 H17A 109.5
O1 C17 H17B 109.5
H17A C17 H17B 109.5
O1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C15 N1 C8 111.5(6)
C15 N1 C7 109.7(6)
C8 N1 C7 109.7(6)
C15 N1 Bi1 117.1(5)
C8 N1 Bi1 105.0(4)
C7 N1 Bi1 103.3(4)
C16 O1 C17 113.5(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Bi1 F1 2.213(4)
Bi1 C14 2.229(7)
Bi1 C1 2.237(7)
Bi1 N1 2.583(6)
C1 C6 1.376(9)
C1 C2 1.388(10)
C6 C5 1.373(11)
C6 C7 1.509(10)
C5 C4 1.357(12)
C5 H5 0.9300
C4 C3 1.374(11)
C4 H4 0.9300
C3 C2 1.389(10)
C3 H3 0.9300
C2 H2 0.9300
C7 N1 1.498(9)
C7 H7A 0.9700
C7 H7B 0.9700
C14 C9 1.394(10)
C14 C13 1.397(11)
C9 C10 1.372(10)
C9 C8 1.501(10)
C10 C11 1.392(13)
C10 H10 0.9300
C11 C12 1.381(14)
C11 H11 0.9300
C12 C13 1.371(12)
C12 H12 0.9300
C13 H13 0.9300
C8 N1 1.485(9)
C8 H8A 0.9700
C8 H8B 0.9700
C15 N1 1.468(9)
C15 C16 1.497(11)
C15 H15A 0.9700
C15 H15B 0.9700
C16 O1 1.399(9)
C16 H16A 0.9700
C16 H16B 0.9700
C17 O1 1.415(10)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
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
C2 C1 C6 C5 0.5(12)
Bi1 C1 C6 C5 176.4(6)
C2 C1 C6 C7 -176.0(7)
Bi1 C1 C6 C7 -0.1(10)
C1 C6 C5 C4 -0.6(14)
C7 C6 C5 C4 175.9(8)
C6 C5 C4 C3 1.3(14)
C5 C4 C3 C2 -2.0(13)
C6 C1 C2 C3 -1.3(11)
Bi1 C1 C2 C3 -177.0(5)
C4 C3 C2 C1 2.0(12)
C5 C6 C7 N1 151.1(7)
C1 C6 C7 N1 -32.3(10)
C13 C14 C9 C10 3.7(11)
Bi1 C14 C9 C10 -169.2(5)
C13 C14 C9 C8 -173.8(6)
Bi1 C14 C9 C8 13.3(8)
C14 C9 C10 C11 -2.1(12)
C8 C9 C10 C11 175.4(7)
C9 C10 C11 C12 -1.7(14)
C10 C11 C12 C13 3.8(15)
C11 C12 C13 C14 -2.1(14)
C9 C14 C13 C12 -1.6(11)
Bi1 C14 C13 C12 171.1(6)
C10 C9 C8 N1 147.7(7)
C14 C9 C8 N1 -34.8(9)
N1 C15 C16 O1 62.4(9)
C16 C15 N1 C8 68.0(8)
C16 C15 N1 C7 -170.3(7)
C16 C15 N1 Bi1 -53.0(8)
C9 C8 N1 C15 -93.7(7)
C9 C8 N1 C7 144.5(6)
C9 C8 N1 Bi1 34.1(7)
C6 C7 N1 C15 167.2(7)
C6 C7 N1 C8 -70.0(8)
C6 C7 N1 Bi1 41.5(7)
C15 C16 O1 C17 -174.7(7)
