#------------------------------------------------------------------------------
#$Date: 2019-11-07 23:07:45 +0100 (jue 07 de nov de 2019) $
#$Revision: 224190 $
#$URL: svn://www.crystallography.net/cod/cif/7/04/97/7049736.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_7049736
loop_
_publ_author_name
'Ritter, Christian'
'Ringler, Benjamin'
'Dankert, Fabian'
'Conrad, Matthias'
'Kraus, Florian'
'von Hänisch, Carsten'
_publ_section_title
;
 Synthesis and crystal structures of novel tertiary butyl substituted
 (pseudo-)halogen bismuthanes.
;
_journal_issue                   16
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5253
_journal_page_last               5262
_journal_paper_doi               10.1039/c9dt00408d
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C9 H18 Bi N'
_chemical_formula_sum            'C9 H18 Bi N'
_chemical_formula_weight         349.22
_chemical_name_systematic        Bis-tert-butylcyanobismutan
_space_group_crystal_system      tetragonal
_space_group_IT_number           94
_space_group_name_Hall           'P 4n 2n'
_space_group_name_H-M_alt        'P 42 21 2'
_symmetry_space_group_name_Hall  'P 4n 2n'
_symmetry_space_group_name_H-M   'P 42 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-23 deposited with the CCDC.    2019-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3118(6)
_cell_length_b                   13.3118(6)
_cell_length_c                   6.2820(3)
_cell_measurement_reflns_used    1102
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.48
_cell_measurement_theta_min      1.53
_cell_volume                     1113.20(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS2'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11435
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_min         2.164
_exptl_absorpt_coefficient_mu    15.787
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'STOE X-AREA, LANA 1.71.3'
_exptl_crystal_colour            beige
_exptl_crystal_density_diffrn    2.084
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.045
_exptl_crystal_size_rad          0.0573
_exptl_transmission_factor_max   0.0656
_exptl_transmission_factor_min   0.0380
_refine_diff_density_max         1.077
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.139
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.49(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.247
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         1104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.247
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0236
_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)+(0.0093P)²+6.6568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0456
_refine_ls_wR_factor_ref         0.0490
_reflns_Friedel_coverage         0.616
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                989
_reflns_number_total             1104
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt00408d1.cif
_cod_data_source_block           tBu2BiCN
_cod_depositor_comments
'Adding full bibliography for 7049733--7049739.cif.'
_cod_original_cell_volume        1113.20(11)
_cod_database_code               7049736
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.51(4)
 0.49(4)
2. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(C002)
4. Others
 Fixed Sof: C002(0.5) N1(0.5)
5.a Idealised Me refined as rotating group:
 C004(H00A,H00B,H00C), C005(H00D,H00E,H00F), C0AA(H0AA,H0AB,H0AC)
;
_shelx_res_file
;
TITL fddx24_d.res in P4(2)2(1)2
    fddx24.res
    created by SHELXL-2018/3 at 12:14:47 on 28-Jun-2018
REM Old TITL DI-TERT-BUTYLCYANOBISMUTHANE
REM SHELXT solution in P4(2)2(1)2
REM R1 0.081, Rweak 0.004, Alpha 0.008, Orientation as input
REM Flack x = 0.491 ( 0.016 ) from Parsons' quotients
REM Formula found by SHELXT: C6 Bi N2
CELL 0.71073 13.3118 13.3118 6.282 90 90 90
ZERR 4 0.0006 0.0006 0.0003 0 0 0
LATT -1
SYMM -X,-Y,+Z
SYMM 0.5-Y,0.5+X,0.5+Z
SYMM 0.5+Y,0.5-X,0.5+Z
SYMM 0.5-X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,0.5-Z
SYMM +Y,+X,-Z
SYMM -Y,-X,-Z
SFAC C H Bi N
UNIT 36 72 4 4
EADP N1 C002

L.S. 10
PLAN  20
BOND $H
LIST 6
fmap 2
acta
TWIN -1 0 0 0 -1 0 0 0 -1 2
OMIT 0 52
OMIT 0 2 0
OMIT 1 1 1
REM <olex2.extras>
REM <HklSrc "%.\\FDDX24.hkl">
REM </olex2.extras>

WGHT    0.009300    6.656800
BASF   0.49010
FVAR       0.31041
BI01  3    0.275307    0.724693    0.500000    10.50000    0.02152    0.02152 =
         0.02118   -0.00067   -0.00067    0.00245
PART -1
C002  1    0.271603    0.722455   -0.073388    10.50000    0.03230    0.02150 =
         0.05926   -0.00344   -0.03151    0.00615
PART 0
C003  1    0.450399    0.744429    0.480739    11.00000    0.01737    0.02300 =
         0.03657    0.00508   -0.01296   -0.00094
C004  1    0.464132    0.850459    0.393436    11.00000    0.02833    0.02278 =
         0.04064   -0.00175   -0.00581   -0.00471
AFIX 137
H00A  2    0.438038    0.853723    0.251141    11.00000   -1.50000
H00B  2    0.534300    0.867099    0.392078    11.00000   -1.50000
H00C  2    0.428702    0.897290    0.482141    11.00000   -1.50000
AFIX   0
C005  1    0.495423    0.667847    0.325394    11.00000    0.02899    0.03471 =
         0.02411   -0.00027    0.00004    0.00928
AFIX 137
H00D  2    0.463460    0.674461    0.189124    11.00000   -1.50000
H00E  2    0.484823    0.601177    0.379150    11.00000   -1.50000
H00F  2    0.566174    0.679953    0.310641    11.00000   -1.50000
AFIX   0
C0AA  1    0.494622    0.734440    0.696675    11.00000    0.02731    0.03641 =
         0.02385   -0.00544   -0.00357   -0.00549
AFIX 137
H0AA  2    0.467530    0.785541    0.787955    11.00000   -1.50000
H0AB  2    0.566239    0.741889    0.688116    11.00000   -1.50000
H0AC  2    0.478691    0.669433    0.753575    11.00000   -1.50000
AFIX   0
PART -1
N1    4    0.282071    0.715997    0.094509    10.50000    0.03230    0.02150 =
         0.05926   -0.00344   -0.03151    0.00615
HKLF 4




REM  fddx24_d.res in P4(2)2(1)2
REM wR2 = 0.0490, GooF = S = 1.247, Restrained GooF = 1.247 for all data
REM R1 = 0.0236 for 989 Fo > 4sig(Fo) and 0.0317 for all 1104 data
REM 58 parameters refined using 0 restraints

END

WGHT      0.0093      6.6433

REM Highest difference peak  1.077,  deepest hole -0.650,  1-sigma level  0.139
Q1    1   0.2126  0.7080  0.4971  11.00000  0.05    1.08
Q2    1   0.3593  0.7230  0.4964  11.00000  0.05    0.82
Q3    1   0.3771  0.7575  0.5064  11.00000  0.05    0.52
Q4    1   0.6341  0.8976  0.5036  11.00000  0.05    0.49
Q5    1   0.4968  0.6591  0.8178  11.00000  0.05    0.48
Q6    1   0.1286  0.7228  0.5032  11.00000  0.05    0.41
Q7    1   0.5649  0.7686  0.8947  11.00000  0.05    0.39
Q8    1   0.3326  0.6805  0.6492  11.00000  0.05    0.39
Q9    1   0.5518  0.8353  0.4959  11.00000  0.05    0.38
Q10   1   0.5621  0.5606  0.4349  11.00000  0.05    0.37
Q11   1   0.5172  0.6123  0.3572  11.00000  0.05    0.37
Q12   1   0.3636  0.6470  0.0665  11.00000  0.05    0.36
Q13   1   0.5445  0.7798  0.9304  11.00000  0.05    0.35
Q14   1   0.5667  0.5709  0.8906  11.00000  0.05    0.34
Q15   1   0.5968  0.6535  0.7850  11.00000  0.05    0.34
Q16   1   0.6611  0.6817  0.4974  11.00000  0.05    0.34
Q17   1   0.2631  0.7218  0.2691  11.00000  0.05    0.34
Q18   1   0.5277  0.6160  0.6387  11.00000  0.05    0.33
Q19   1   0.4008  0.9576  0.4891  11.00000  0.05    0.33
Q20   1   0.4565  0.5460  0.4306  11.00000  0.05    0.32
;
_shelx_res_checksum              18155
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'y, x, -z'
'-y, -x, -z'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.27531(2) 0.72469(2) 0.500000 0.02141(13) Uani 1 2 d S T P . .
C1 C 0.272(6) 0.722(6) -0.073(6) 0.038(5) Uani 0.5 1 d . . . A -1
C2 C 0.4504(6) 0.7444(6) 0.481(4) 0.026(3) Uani 1 1 d . . . . .
C4 C 0.4641(8) 0.8505(7) 0.3934(17) 0.031(2) Uani 1 1 d . . . . .
H00A H 0.438038 0.853723 0.251141 0.046 Uiso 1 1 calc GR . . . .
H00B H 0.534300 0.867099 0.392078 0.046 Uiso 1 1 calc GR . . . .
H00C H 0.428702 0.897290 0.482141 0.046 Uiso 1 1 calc GR . . . .
C3 C 0.4954(8) 0.6678(9) 0.3254(16) 0.029(2) Uani 1 1 d . . . . .
H00D H 0.463460 0.674461 0.189124 0.044 Uiso 1 1 calc GR . . . .
H00E H 0.484823 0.601177 0.379150 0.044 Uiso 1 1 calc GR . . . .
H00F H 0.566174 0.679953 0.310641 0.044 Uiso 1 1 calc GR . . . .
C5 C 0.4946(8) 0.7344(9) 0.6967(15) 0.029(2) Uani 1 1 d . . . . .
H0AA H 0.467530 0.785541 0.787955 0.044 Uiso 1 1 calc GR . . . .
H0AB H 0.566239 0.741889 0.688116 0.044 Uiso 1 1 calc GR . . . .
H0AC H 0.478691 0.669433 0.753575 0.044 Uiso 1 1 calc GR . . . .
N1 N 0.282(5) 0.716(5) 0.095(5) 0.038(5) Uani 0.5 1 d . . . A -1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Bi1 0.02152(15) 0.02152(15) 0.02118(19) -0.0007(6) -0.0007(6) 0.00245(17)
C1 0.03(2) 0.021(19) 0.059(7) -0.003(12) -0.032(13) 0.006(7)
C2 0.017(4) 0.023(4) 0.037(8) 0.005(7) -0.013(8) -0.001(3)
C4 0.028(5) 0.023(5) 0.041(6) -0.002(4) -0.006(5) -0.005(4)
C3 0.029(6) 0.035(6) 0.024(5) 0.000(5) 0.000(4) 0.009(5)
C5 0.027(5) 0.036(6) 0.024(5) -0.005(5) -0.004(4) -0.005(5)
N1 0.03(2) 0.021(19) 0.059(7) -0.003(12) -0.032(13) 0.006(7)
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'
Bi Bi -4.1077 10.2566 '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'
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
C2 Bi1 C2 103.0(4) . 8_666
C2 Bi1 N1 85.3(17) . .
C2 Bi1 N1 90.6(16) 8_666 .
C4 C2 Bi1 103.9(6) . .
C4 C2 C3 109.9(14) . .
C3 C2 Bi1 110.3(8) . .
C5 C2 Bi1 109.7(10) . .
C5 C2 C4 111.3(10) . .
C5 C2 C3 111.5(9) . .
C2 C4 H00A 109.5 . .
C2 C4 H00B 109.5 . .
C2 C4 H00C 109.5 . .
H00A C4 H00B 109.5 . .
H00A C4 H00C 109.5 . .
H00B C4 H00C 109.5 . .
C2 C3 H00D 109.5 . .
C2 C3 H00E 109.5 . .
C2 C3 H00F 109.5 . .
H00D C3 H00E 109.5 . .
H00D C3 H00F 109.5 . .
H00E C3 H00F 109.5 . .
C2 C5 H0AA 109.5 . .
C2 C5 H0AB 109.5 . .
C2 C5 H0AC 109.5 . .
H0AA C5 H0AB 109.5 . .
H0AA C5 H0AC 109.5 . .
H0AB C5 H0AC 109.5 . .
C1 N1 Bi1 168(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 C2 2.349(8) .
Bi1 C2 2.349(8) 8_666
Bi1 N1 2.55(3) .
C1 N1 1.07(2) .
C2 C4 1.525(15) .
C2 C3 1.533(18) .
C2 C5 1.48(2) .
C4 H00A 0.9600 .
C4 H00B 0.9600 .
C4 H00C 0.9600 .
C3 H00D 0.9600 .
C3 H00E 0.9600 .
C3 H00F 0.9600 .
C5 H0AA 0.9600 .
C5 H0AB 0.9600 .
C5 H0AC 0.9600 .
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.51(4)
2 0.49(4)
