#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:35:57 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179337 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/34/4323476.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_4323476
loop_
_publ_author_name
'Claire J. Carmalt'
'Alan H. Cowley'
'Robert D. Culp'
'Richard A. Jones'
'Smuruthi Kamepalli'
'Nicholas C. Norman'
_publ_section_title
;
 Synthesis and Structures of Intramolecularly Base-Coordinated Group 15
 Aryl Halides
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2770
_journal_page_last               2776
_journal_paper_doi               10.1021/ic9701165
_journal_volume                  36
_journal_year                    1997
_chemical_formula_moiety         '[(C6H4CH2NMe2)2BiCl]'
_chemical_formula_sum            'C18 H24 Bi Cl N2'
_chemical_formula_weight         512.82
_chemical_name_common            'compound 5'
_chemical_name_systematic
;
?
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 104.536(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9498(10)
_cell_length_b                   11.4695(11)
_cell_length_c                   13.9456(8)
_cell_measurement_reflns_used    37
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.44
_cell_measurement_theta_min      12.25
_cell_volume                     1850.2(3)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measurement_device       'Siemens P4'
_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  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0662
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11673
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        3.4
_diffrn_standards_interval_count 96
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    9.672
_exptl_absorpt_correction_T_max  0.50404
_exptl_absorpt_correction_T_min  0.31933
_exptl_absorpt_correction_type   SHELXA
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.34
_refine_diff_density_max         1.351
_refine_diff_density_min         -1.662
_refine_diff_density_rms         0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.078
_refine_ls_goodness_of_fit_obs   1.130
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         5392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_restrained_S_obs      1.130
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_obs          0.0375
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0417P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0906
_refine_ls_wR_factor_obs         0.0827
_reflns_number_observed          4147
_reflns_number_total             5393
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic9701165_2.cif
_cod_data_source_block           c15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4323476
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_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Bi1 Bi 0.15856(2) 0.84037(2) 0.020384(14) 0.01568(6) Uani 1 d . .
Cl1 Cl 0.06905(14) 0.77115(15) 0.16791(12) 0.0313(3) Uani 1 d . .
N1 N 0.2604(4) 0.9531(4) -0.0927(3) 0.0220(10) Uani 1 d . .
N2 N 0.2137(4) 0.6028(4) -0.0541(3) 0.0217(10) Uani 1 d . .
C1 C 0.1873(4) 1.0241(5) 0.0797(4) 0.0160(10) Uani 1 d . .
C2 C 0.2514(5) 1.0997(5) 0.0337(4) 0.0192(11) Uani 1 d . .
C3 C 0.2498(5) 1.2195(5) 0.0513(4) 0.0230(12) Uani 1 d . .
H3 H 0.2910(5) 1.2708(5) 0.0190(4) 0.023(6) Uiso 1 calc R .
C4 C 0.1888(5) 1.2643(5) 0.1151(5) 0.0244(12) Uani 1 d . .
H4 H 0.1870(5) 1.3461(5) 0.1252(5) 0.023(6) Uiso 1 calc R .
C5 C 0.1305(5) 1.1905(6) 0.1641(4) 0.0249(13) Uani 1 d . .
H5 H 0.0916(5) 1.2213(6) 0.2101(4) 0.023(6) Uiso 1 calc R .
C6 C 0.1286(5) 1.0694(5) 0.1459(4) 0.0186(11) Uani 1 d . .
H6 H 0.0873(5) 1.0188(5) 0.1787(4) 0.023(6) Uiso 1 calc R .
C7 C 0.3229(5) 1.0493(5) -0.0309(4) 0.0238(12) Uani 1 d . .
H7A H 0.3410(5) 1.1111(5) -0.0742(4) 0.032(10) Uiso 1 calc R .
H7B H 0.3968(5) 1.0196(5) 0.0112(4) 0.032(10) Uiso 1 calc R .
C8 C 0.1703(6) 1.0002(6) -0.1740(4) 0.0286(14) Uani 1 d . .
H8A H 0.1200(22) 1.0518(29) -0.1474(5) 0.035(6) Uiso 1 calc R .
H8B H 0.1244(23) 0.9361(6) -0.2105(19) 0.035(6) Uiso 1 calc R .
H8C H 0.2059(6) 1.0445(31) -0.2187(17) 0.035(6) Uiso 1 calc R .
C9 C 0.3432(6) 0.8840(7) -0.1310(5) 0.0337(15) Uani 1 d . .
H9A H 0.4044(22) 0.8549(33) -0.0755(5) 0.035(6) Uiso 1 calc R .
H9B H 0.3774(29) 0.9329(12) -0.1738(27) 0.035(6) Uiso 1 calc R .
H9C H 0.3031(10) 0.8179(22) -0.1693(28) 0.035(6) Uiso 1 calc R .
C10 C 0.3329(5) 0.7731(5) 0.1066(4) 0.0155(10) Uani 1 d . .
C11 C 0.3559(5) 0.6538(5) 0.1017(4) 0.0191(10) Uani 1 d . .
C12 C 0.4643(5) 0.6111(6) 0.1517(4) 0.0268(13) Uani 1 d . .
H12 H 0.4811(5) 0.5305(6) 0.1474(4) 0.023(6) Uiso 1 calc R .
C13 C 0.5482(5) 0.6851(6) 0.2078(5) 0.0285(14) Uani 1 d . .
H13 H 0.6221(5) 0.6551(6) 0.2402(5) 0.023(6) Uiso 1 calc R .
C14 C 0.5242(5) 0.8016(6) 0.2166(4) 0.0249(12) Uani 1 d . .
H14 H 0.5800(5) 0.8517(6) 0.2569(4) 0.023(6) Uiso 1 calc R .
C15 C 0.4162(5) 0.8450(6) 0.1651(4) 0.0211(11) Uani 1 d . .
H15 H 0.3996(5) 0.9254(6) 0.1702(4) 0.023(6) Uiso 1 calc R .
C16 C 0.2620(5) 0.5715(5) 0.0492(4) 0.0210(11) Uani 1 d . .
H16A H 0.2940(5) 0.4915(5) 0.0524(4) 0.032(10) Uiso 1 calc R .
H16B H 0.1993(5) 0.5711(5) 0.0841(4) 0.032(10) Uiso 1 calc R .
C17 C 0.2933(6) 0.5732(7) -0.1147(5) 0.034(2) Uani 1 d . .
H17A H 0.2621(20) 0.6016(34) -0.1824(10) 0.035(6) Uiso 1 calc R .
H17B H 0.3028(30) 0.4883(7) -0.1157(27) 0.035(6) Uiso 1 calc R .
H17C H 0.3685(13) 0.6097(32) -0.0865(20) 0.035(6) Uiso 1 calc R .
C18 C 0.1008(5) 0.5469(6) -0.0942(5) 0.035(2) Uani 1 d . .
H18A H 0.0694(17) 0.5719(29) -0.1629(12) 0.035(6) Uiso 1 calc R .
H18B H 0.0475(12) 0.5696(30) -0.0544(20) 0.035(6) Uiso 1 calc R .
H18C H 0.1102(8) 0.4620(7) -0.0921(28) 0.035(6) Uiso 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C1 Bi1 C10 95.1(2) . . ?
C1 Bi1 N1 72.7(2) . . ?
C10 Bi1 N1 89.0(2) . . ?
C1 Bi1 Cl1 92.81(13) . . ?
C10 Bi1 Cl1 89.01(13) . . ?
N1 Bi1 Cl1 165.15(11) . . ?
C1 Bi1 N2 159.0(2) . . ?
C10 Bi1 N2 68.1(2) . . ?
N1 Bi1 N2 93.71(14) . . ?
Cl1 Bi1 N2 99.19(10) . . ?
C8 N1 C9 110.5(5) . . ?
C8 N1 C7 110.0(5) . . ?
C9 N1 C7 109.0(5) . . ?
C8 N1 Bi1 107.0(4) . . ?
C9 N1 Bi1 114.7(4) . . ?
C7 N1 Bi1 105.4(3) . . ?
C16 N2 C17 111.1(5) . . ?
C16 N2 C18 111.5(5) . . ?
C17 N2 C18 110.3(5) . . ?
C16 N2 Bi1 87.1(3) . . ?
C17 N2 Bi1 129.2(4) . . ?
C18 N2 Bi1 105.2(4) . . ?
C6 C1 C2 119.5(5) . . ?
C6 C1 Bi1 122.3(4) . . ?
C2 C1 Bi1 117.2(4) . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 C7 121.2(5) . . ?
C1 C2 C7 119.3(5) . . ?
C4 C3 C2 120.7(5) . . ?
C5 C4 C3 120.3(6) . . ?
C4 C5 C6 120.1(5) . . ?
C1 C6 C5 119.9(5) . . ?
N1 C7 C2 110.8(5) . . ?
C15 C10 C11 119.2(5) . . ?
C15 C10 Bi1 122.5(4) . . ?
C11 C10 Bi1 118.2(4) . . ?
C12 C11 C10 119.2(6) . . ?
C12 C11 C16 120.4(5) . . ?
C10 C11 C16 120.3(5) . . ?
C13 C12 C11 120.8(6) . . ?
C14 C13 C12 120.3(6) . . ?
C13 C14 C15 118.9(6) . . ?
C10 C15 C14 121.5(6) . . ?
N2 C16 C11 112.8(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C1 2.258(6) . ?
Bi1 C10 2.264(5) . ?
Bi1 N1 2.570(5) . ?
Bi1 Cl1 2.6668(15) . ?
Bi1 N2 3.047(5) . ?
N1 C8 1.458(7) . ?
N1 C9 1.469(8) . ?
N1 C7 1.481(7) . ?
N2 C16 1.456(7) . ?
N2 C17 1.462(7) . ?
N2 C18 1.471(8) . ?
C1 C6 1.393(7) . ?
C1 C2 1.413(8) . ?
C2 C3 1.396(8) . ?
C2 C7 1.504(7) . ?
C3 C4 1.383(8) . ?
C4 C5 1.382(9) . ?
C5 C6 1.411(8) . ?
C10 C15 1.389(8) . ?
C10 C11 1.400(8) . ?
C11 C12 1.396(8) . ?
C11 C16 1.509(8) . ?
C12 C13 1.394(9) . ?
C13 C14 1.379(9) . ?
C14 C15 1.401(8) . ?
