#------------------------------------------------------------------------------
#$Date: 2016-06-23 09:23:56 +0300 (Thu, 23 Jun 2016) $
#$Revision: 183879 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/56/7225653.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_7225653
loop_
_publ_author_name
'Adonin, Sergey A.'
'Perekalin, Dmitry S.'
'Gorokh, Igor D.'
'Samsonenko, Denis G.'
'Sokolov, Maksim Nailyevich'
'Fedin, Vladimir P.'
_publ_section_title
;
 Heterogeneous bromination of alkenes using Bi(III) polybromide complexes
 as {Br2} source
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA10109G
_journal_year                    2016
_chemical_formula_sum            'C15 H18 Bi2 Br11 N3'
_chemical_formula_weight         1537.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-04-18 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.370(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8459(2)
_cell_length_b                   23.3803(4)
_cell_length_c                   9.4868(2)
_cell_measurement_reflns_used    4300
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      28.96
_cell_measurement_theta_min      3.78
_cell_volume                     1631.43(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8267
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        26.500
_diffrn_reflns_theta_max         29.535
_diffrn_reflns_theta_min         3.272
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    24.254
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    3.129
_exptl_crystal_description       plate
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.274
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0237P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0532
_refine_ls_wR_factor_ref         0.0556
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3420
_reflns_number_total             3879
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c6ra10109g2.cif
_cod_data_source_block           sa1160
_cod_database_code               7225653
_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.
;
_shelx_estimated_absorpt_t_min   0.112
_shelx_estimated_absorpt_t_max   0.530
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
Bi1 Bi 0.35506(2) 0.33456(2) 0.65779(2) 0.01627(6) Uani 1 1 d . . .
Br1 Br 0.16200(6) 0.40011(2) 0.78404(5) 0.02838(12) Uani 1 1 d . . .
Br2 Br 0.24951(7) 0.40680(2) 0.40986(5) 0.02986(13) Uani 1 1 d . . .
Br3 Br 0.65487(6) 0.39935(2) 0.78716(6) 0.02973(13) Uani 1 1 d . . .
Br4 Br 0.55570(8) 0.2500 0.52857(7) 0.02390(15) Uani 1 2 d S T P
Br5 Br 0.46371(9) 0.2500 0.91173(7) 0.02598(16) Uani 1 2 d S T P
Br6 Br 0.04435(8) 0.2500 0.52939(7) 0.02356(15) Uani 1 2 d S T P
Br7 Br 0.05307(6) 0.47245(2) 0.10820(5) 0.02498(11) Uani 1 1 d . . .
N1 N 0.2327(7) 0.6154(3) 0.5810(6) 0.0582(17) Uani 1 1 d . . .
H1 H 0.1626 0.6367 0.5071 0.070 Uiso 1 1 calc R U .
C11 C 0.3236(8) 0.6392(3) 0.7209(7) 0.0475(16) Uani 1 1 d . . .
H11 H 0.3104 0.6786 0.7391 0.057 Uiso 1 1 calc R U .
C12 C 0.4322(8) 0.6047(4) 0.8317(7) 0.056(2) Uani 1 1 d . . .
H12 H 0.4965 0.6199 0.9285 0.068 Uiso 1 1 calc R U .
C13 C 0.4478(9) 0.5478(4) 0.8022(8) 0.061(2) Uani 1 1 d . . .
H13 H 0.5241 0.5235 0.8782 0.073 Uiso 1 1 calc R U .
C14 C 0.3563(7) 0.5273(3) 0.6676(7) 0.0354(13) Uani 1 1 d . . .
H14 H 0.3662 0.4877 0.6492 0.042 Uiso 1 1 calc R U .
C15 C 0.2530(8) 0.5592(3) 0.5593(7) 0.0424(15) Uani 1 1 d . . .
H15 H 0.1909 0.5427 0.4636 0.051 Uiso 1 1 calc R U .
N2 N 0.9482(6) 0.2220(2) 0.9039(5) 0.0377(13) Uani 0.5 1 d . . P
H2 H 0.8915 0.2036 0.8196 0.045 Uiso 1 1 calc R U .
C21 C 0.9482(6) 0.2220(2) 0.9039(5) 0.0377(13) Uani 0.5 1 d . . P
C22 C 1.0315(9) 0.1924(3) 1.0279(7) 0.0490(16) Uani 1 1 d . . .
H22 H 1.0272 0.1518 1.0266 0.059 Uiso 1 1 calc R U .
C23 C 1.1235(10) 0.2210(3) 1.1573(6) 0.066(2) Uani 1 1 d . . .
H23 H 1.1869 0.2004 1.2466 0.079 Uiso 1 1 calc R U .
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'
Br Br -0.2901 2.4595 '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_publ_flag
Br1 Bi1 Br2 89.002(16) . yes
Br1 Bi1 Br4 173.854(15) . yes
Br1 Bi1 Br5 93.673(16) . yes
Br1 Bi1 Br6 92.934(15) . yes
Br2 Bi1 Br4 95.604(16) . yes
Br2 Bi1 Br5 176.253(15) . yes
Br2 Bi1 Br6 95.446(16) . yes
Br3 Bi1 Br1 90.819(16) . yes
Br3 Bi1 Br2 89.972(16) . yes
Br3 Bi1 Br4 93.245(16) . yes
Br3 Bi1 Br5 92.609(16) . yes
Br3 Bi1 Br6 173.458(15) . yes
Br4 Bi1 Br6 82.599(14) . yes
Br5 Bi1 Br4 81.545(15) . yes
Br5 Bi1 Br6 81.810(15) . yes
Bi1 Br4 Bi1 81.179(16) 4_565 yes
Bi1 Br5 Bi1 82.397(17) 4_565 yes
Bi1 Br6 Bi1 80.993(15) 4_565 yes
C11 N1 H1 120.4 . ?
C15 N1 H1 120.4 . ?
C15 N1 C11 119.3(6) . ?
N1 C11 H11 120.8 . ?
C12 C11 N1 118.4(6) . ?
C12 C11 H11 120.8 . ?
C11 C12 H12 120.3 . ?
C11 C12 C13 119.5(6) . ?
C13 C12 H12 120.3 . ?
C12 C13 H13 120.2 . ?
C14 C13 C12 119.5(6) . ?
C14 C13 H13 120.2 . ?
C13 C14 H14 118.8 . ?
C15 C14 C13 122.4(6) . ?
C15 C14 H14 118.8 . ?
N1 C15 H15 119.6 . ?
C14 C15 N1 120.9(6) . ?
C14 C15 H15 119.6 . ?
C21 N2 H2 119.3 4_565 ?
C21 N2 C22 121.5(3) 4_565 ?
C22 N2 H2 119.3 . ?
N2 C22 H22 120.4 . ?
N2 C22 C23 119.2(6) . ?
C23 C22 H22 120.4 . ?
C22 C23 H23 120.3 . ?
C23 C23 C22 119.3(4) 4_565 ?
C23 C23 H23 120.3 4_565 ?
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 Br1 2.7094(5) . yes
Bi1 Br2 2.7776(5) . yes
Bi1 Br3 2.7064(5) . yes
Bi1 Br4 3.0386(5) . yes
Bi1 Br5 3.0015(5) . yes
Bi1 Br6 3.0444(5) . yes
Br4 Bi1 3.0386(5) 4_565 ?
Br5 Bi1 3.0015(5) 4_565 ?
Br6 Bi1 3.0443(5) 4_565 ?
Br7 Br7 2.3190(9) 3_565 yes
N1 H1 0.8800 . ?
N1 C11 1.386(8) . ?
N1 C15 1.348(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.363(9) . ?
C12 H12 0.9500 . ?
C12 C13 1.373(10) . ?
C13 H13 0.9500 . ?
C13 C14 1.318(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.299(8) . ?
C15 H15 0.9500 . ?
N2 H2 0.8800 . ?
N2 C21 1.308(10) 4_565 ?
N2 C22 1.325(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.362(8) . ?
C23 C23 1.357(14) 4_565 ?
C23 H23 0.9500 . ?
