# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_035
_database_code_depnum_ccdc_archive 'CCDC 1452481'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_common            'N,N-dimethylbipyridinium dibromide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 Br2 N2'
_chemical_formula_sum            'C12 H14 Br2 N2'
_chemical_formula_weight         346.07

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   5.947(3)
_cell_length_b                   8.068(8)
_cell_length_c                   13.411(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.94(3)
_cell_angle_gamma                90.00
_cell_volume                     640.0(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       350000
_cell_measurement_reflns_used    2131
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      27.23

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    6.308
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.223
_exptl_absorpt_correction_T_max  0.352
_exptl_absorpt_process_details   
;
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467

Data were collected at room temperature and pressure of 0.35(5) GPa
 (350000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       
; 
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168; 
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2131
_diffrn_reflns_av_R_equivalents  0.2281
_diffrn_reflns_av_sigmaI/netI    0.0886
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.23
_reflns_number_total             313
_reflns_number_gt                285
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 2008'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1797P)²+1.5200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         313
_refine_ls_number_parameters     39
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0879
_refine_ls_wR_factor_ref         0.2400
_refine_ls_wR_factor_gt          0.2298
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.3234(3) 0.4189(5) 0.32436(12) 0.042(3) Uani 1 1 d . . .
N1 N 0.983(2) 0.233(4) 0.5694(10) 0.040(4) Uiso 1 1 d . . .
C2 C 0.863(3) 0.158(5) 0.6350(13) 0.041(5) Uiso 1 1 d . . .
H2 H 0.9219 0.1616 0.7019 0.049 Uiso 1 1 calc R . .
C3 C 0.674(3) 0.081(5) 0.6155(14) 0.043(5) Uiso 1 1 d . . .
H3 H 0.5850 0.0528 0.6659 0.052 Uiso 1 1 calc R . .
C4 C 0.608(2) 0.042(3) 0.5132(10) 0.019(3) Uiso 1 1 d . . .
C5 C 0.726(3) 0.116(4) 0.4449(13) 0.035(5) Uiso 1 1 d . . .
H5 H 0.6861 0.0944 0.3774 0.042 Uiso 1 1 calc R . .
C6 C 0.909(2) 0.225(5) 0.4715(11) 0.037(5) Uiso 1 1 d . . .
H6 H 0.9734 0.2884 0.4239 0.045 Uiso 1 1 calc R . .
C7 C 1.178(3) 0.358(5) 0.5981(13) 0.044(5) Uiso 1 1 d . . .
H7A H 1.2388 0.3953 0.5384 0.053 Uiso 1 1 calc R . .
H7B H 1.2947 0.3047 0.6414 0.053 Uiso 1 1 calc R . .
H7C H 1.1205 0.4511 0.6321 0.053 Uiso 1 1 calc R . .

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
Br1 0.053(2) 0.025(12) 0.0475(17) -0.0041(13) 0.0081(13) -0.0090(12)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
N1 C2 1.33(3) . ?
N1 C6 1.34(2) . ?
N1 C7 1.56(4) . ?
C2 C3 1.28(3) . ?
C3 C4 1.42(2) . ?
C4 C5 1.35(3) . ?
C4 C4 1.46(4) 3_656 ?
C5 C6 1.41(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
C2 N1 C6 118.7(18) . . ?
C2 N1 C7 124.6(15) . . ?
C6 N1 C7 115.6(18) . . ?
C3 C2 N1 126.9(17) . . ?
C2 C3 C4 116.9(18) . . ?
C5 C4 C3 116(2) . . ?
C5 C4 C4 123.2(16) . 3_656 ?
C3 C4 C4 119.0(17) . 3_656 ?
C4 C5 C6 123.0(16) . . ?
N1 C6 C5 116(2) . . ?

_diffrn_measured_fraction_theta_max 0.218
_diffrn_reflns_theta_full        27.23
_diffrn_measured_fraction_theta_full 0.218
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.146
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_01M
_database_code_depnum_ccdc_archive 'CCDC 1452482'
_audit_update_record             
;
2016-02-10 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_common            "44'-bipyridine hydrobromide"
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Br2 N2'
_chemical_formula_sum            'C10 H10 Br2 N2'
_chemical_formula_weight         318.02

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8986(6)
_cell_length_b                   7.6614(10)
_cell_length_c                   7.9890(9)
_cell_angle_alpha                70.464(11)
_cell_angle_beta                 87.005(10)
_cell_angle_gamma                77.176(11)
_cell_volume                     275.44(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3434
_cell_measurement_theta_min      4.27
_cell_measurement_theta_max      25.29

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             154
_exptl_absorpt_coefficient_mu    7.319
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.311
_exptl_absorpt_correction_T_max  0.542
_exptl_absorpt_process_details   
;
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467

Data were collected at room temperature and pressure of 0.02(5) GPa
 (20000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3434
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.27
_diffrn_reflns_theta_max         25.29
_reflns_number_total             905
_reflns_number_gt                875
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury (2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0273P)²+0.0574P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         905
_refine_ls_number_parameters     64
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0184
_refine_ls_wR_factor_ref         0.0451
_refine_ls_wR_factor_gt          0.0448
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.11792(4) 0.34083(3) 0.82683(3) 0.04087(12) Uani 1 1 d . . .
N1 N 0.5738(4) 0.6811(3) 0.7450(3) 0.0404(5) Uani 1 1 d . . .
H1 H 0.7198 0.6056 0.8044 0.048 Uiso 1 1 calc R . .
C2 C 0.3898(5) 0.7786(4) 0.8250(3) 0.0445(6) Uani 1 1 d . . .
H2 H 0.4152 0.7615 0.9445 0.053 Uiso 1 1 calc R . .
C3 C 0.1593(5) 0.9062(3) 0.7306(3) 0.0383(5) Uani 1 1 d . . .
H3 H 0.0299 0.9762 0.7862 0.046 Uiso 1 1 calc R . .
C4 C 0.1209(4) 0.9300(3) 0.5533(3) 0.0272(5) Uani 1 1 d . . .
C5 C 0.3181(4) 0.8187(3) 0.4773(3) 0.0372(5) Uani 1 1 d . . .
H5 H 0.2966 0.8288 0.3592 0.045 Uiso 1 1 calc R . .
C6 C 0.5434(5) 0.6945(3) 0.5773(4) 0.0427(6) Uani 1 1 d . . .
H6 H 0.6749 0.6198 0.5272 0.051 Uiso 1 1 calc R . .

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
Br1 0.03778(16) 0.04343(17) 0.03780(19) -0.01461(13) -0.00625(11) 0.00189(10)
N1 0.0298(10) 0.0352(10) 0.0444(14) 0.0008(10) -0.0089(9) -0.0032(8)
C2 0.0455(14) 0.0507(14) 0.0315(14) -0.0070(12) -0.0104(11) -0.0064(11)
C3 0.0402(12) 0.0408(12) 0.0305(14) -0.0120(11) -0.0042(10) -0.0006(10)
C4 0.0284(10) 0.0272(10) 0.0255(12) -0.0063(9) -0.0018(8) -0.0082(8)
C5 0.0365(12) 0.0404(12) 0.0319(13) -0.0135(11) -0.0016(10) 0.0004(9)
C6 0.0336(12) 0.0405(13) 0.0484(16) -0.0130(12) 0.0014(11) 0.0008(9)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
N1 C2 1.319(3) . ?
N1 C6 1.323(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.396(3) . ?
C4 C4 1.487(4) 2_576 ?
C5 C6 1.371(3) . ?

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
C2 N1 C6 122.8(2) . . ?
N1 C2 C3 119.7(2) . . ?
C2 C3 C4 120.0(2) . . ?
C3 C4 C5 117.8(2) . . ?
C3 C4 C4 121.3(2) . 2_576 ?
C5 C4 C4 121.0(2) . 2_576 ?
C6 C5 C4 119.8(2) . . ?
N1 C6 C5 120.0(2) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 -2.5(3) . . . . ?
N1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C2 C3 C4 C4 -178.3(2) . . . 2_576 ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C4 C4 C5 C6 178.2(2) 2_576 . . . ?
C2 N1 C6 C5 2.3(3) . . . . ?
C4 C5 C6 N1 -0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.907
_diffrn_reflns_theta_full        25.29
_diffrn_measured_fraction_theta_full 0.907
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.058
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_01G
_database_code_depnum_ccdc_archive 'CCDC 1452483'
_audit_update_record             
;
2016-02-10 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97

_chemical_name_systematic        'bipyridine hydrobromide'
_chemical_name_common            'bipyridine hydrobromide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Br2 N2'
_chemical_formula_sum            'C10 H10 Br2 N2'
_chemical_formula_weight         318.02

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8839(15)
_cell_length_b                   7.622(5)
_cell_length_c                   7.951(4)
_cell_angle_alpha                70.87(6)
_cell_angle_beta                 86.78(4)
_cell_angle_gamma                77.39(5)
_cell_volume                     272.8(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       10000
_cell_measurement_reflns_used    1219
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.71

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             154
_exptl_absorpt_coefficient_mu    7.389
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.255
_exptl_absorpt_correction_T_max  0.440
_exptl_absorpt_process_details   
;
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467

Data were collected at room temperature and pressure of 0.01(5) GPa
 (10000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1219
_diffrn_reflns_av_R_equivalents  0.1986
_diffrn_reflns_av_sigmaI/netI    0.0841
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         27.71
_reflns_number_total             183
_reflns_number_gt                173
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury (2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0580P)²+1.1229P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         183
_refine_ls_number_parameters     22
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1523
_refine_ls_wR_factor_gt          0.1467
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_restrained_S_all      1.211
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.1207(3) 0.3390(13) 0.8257(4) 0.045(18) Uani 1 1 d . . .
N1 N 0.580(2) 0.668(6) 0.7486(16) 0.035(4) Uiso 1 1 d G . .
H1 H 0.7224 0.5897 0.8096 0.042 Uiso 1 1 calc R . .
C2 C 0.387(2) 0.779(6) 0.8267(15) 0.034(5) Uiso 1 1 d G . .
H2 H 0.4111 0.7698 0.9448 0.041 Uiso 1 1 calc R . .
C3 C 0.157(2) 0.906(6) 0.7282(19) 0.059(10) Uiso 1 1 d G . .
H3 H 0.0274 0.9804 0.7804 0.071 Uiso 1 1 calc R . .
C4 C 0.120(2) 0.920(5) 0.5517(17) 0.021(4) Uiso 1 1 d G . .
C5 C 0.314(2) 0.808(6) 0.4736(16) 0.035(5) Uiso 1 1 d G . .
H5 H 0.2895 0.8180 0.3555 0.042 Uiso 1 1 calc R . .
C6 C 0.544(2) 0.682(5) 0.5721(19) 0.043(6) Uiso 1 1 d G . .
H6 H 0.6731 0.6074 0.5199 0.051 Uiso 1 1 calc R . .

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
Br1 0.0397(12) 0.06(4) 0.032(3) -0.023(10) -0.0053(12) -0.002(4)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
N1 C2 1.3900 . ?
N1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C4 C4 1.54(3) 2_576 ?
C5 C6 1.3900 . ?

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
C2 N1 C6 120.0 . . ?
N1 C2 C3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 C4 116(3) . 2_576 ?
C5 C4 C4 124(2) . 2_576 ?
C6 C5 C4 120.0 . . ?
C5 C6 N1 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.142
_diffrn_reflns_theta_full        27.71
_diffrn_measured_fraction_theta_full 0.142
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.091
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_02G
_database_code_depnum_ccdc_archive 'CCDC 1452484'
_audit_update_record             
;
2016-02-10 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97

_chemical_name_systematic        'bipyridine hydrobromide'
_chemical_name_common            'bipyridine hydrobromide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Br2 N2'
_chemical_formula_sum            'C10 H10 Br2 N2'
_chemical_formula_weight         318.02

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.874(4)
_cell_length_b                   7.567(6)
_cell_length_c                   7.936(4)
_cell_angle_alpha                70.73(6)
_cell_angle_beta                 86.64(5)
_cell_angle_gamma                77.47(7)
_cell_volume                     269.7(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       20000
_cell_measurement_reflns_used    1159
_cell_measurement_theta_min      4.65
_cell_measurement_theta_max      27.20

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.958
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             154
_exptl_absorpt_coefficient_mu    7.476
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.324
_exptl_absorpt_correction_T_max  0.403
_exptl_absorpt_process_details   
;
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467

Data were collected at room temperature and pressure of 0.02(5) GPa
 (20000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1159
_diffrn_reflns_av_R_equivalents  0.0953
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.65
_diffrn_reflns_theta_max         27.20
_reflns_number_total             185
_reflns_number_gt                168
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury (2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0973P)²+0.2782P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         185
_refine_ls_number_parameters     34
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1238
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.1212(6) 0.3431(7) 0.82626(15) 0.044(5) Uani 1 1 d U . .
N1 N 0.567(6) 0.694(7) 0.7544(16) 0.032(2) Uiso 1 1 d . . .
H1 H 0.7127 0.6256 0.8186 0.038 Uiso 1 1 calc R . .
C2 C 0.372(6) 0.802(8) 0.832(2) 0.036(3) Uiso 1 1 d . . .
H2 H 0.3947 0.7961 0.9490 0.043 Uiso 1 1 calc R . .
C3 C 0.150(6) 0.914(8) 0.7355(18) 0.033(3) Uiso 1 1 d . . .
H3 H 0.0108 0.9847 0.7865 0.040 Uiso 1 1 calc R . .
C4 C 0.123(5) 0.927(7) 0.5515(14) 0.025(3) Uiso 1 1 d . . .
C5 C 0.325(7) 0.810(9) 0.481(2) 0.035(3) Uiso 1 1 d . . .
H5 H 0.3037 0.8194 0.3621 0.042 Uiso 1 1 calc R . .
C6 C 0.556(6) 0.681(8) 0.5775(18) 0.044(4) Uiso 1 1 d . . .
H6 H 0.6863 0.5980 0.5338 0.053 Uiso 1 1 calc R . .

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
Br1 0.039(3) 0.052(11) 0.0369(11) -0.015(3) -0.0043(14) -0.002(5)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
N1 C2 1.37(7) . ?
N1 C6 1.44(4) . ?
C2 C3 1.32(4) . ?
C3 C4 1.44(3) . ?
C4 C5 1.40(8) . ?
C4 C4 1.51(7) 2_576 ?
C5 C6 1.39(5) . ?

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
C2 N1 C6 127(3) . . ?
N1 C2 C3 118(3) . . ?
C2 C3 C4 120(4) . . ?
C3 C4 C5 119(3) . . ?
C3 C4 C4 116(5) . 2_576 ?
C5 C4 C4 125(3) . 2_576 ?
C6 C5 C4 124(2) . . ?
N1 C6 C5 111(4) . . ?

_diffrn_measured_fraction_theta_max 0.153
_diffrn_reflns_theta_full        27.20
_diffrn_measured_fraction_theta_full 0.153
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.100
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_05G
_database_code_depnum_ccdc_archive 'CCDC 1452485'
_audit_update_record             
;
2016-02-10 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97

_chemical_name_systematic        'bipyridine hydrobromide'
_chemical_name_common            'bipyridine hydrobromide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Br2 N2'
_chemical_formula_sum            'C10 H10 Br2 N2'
_chemical_formula_weight         318.02

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8450(11)
_cell_length_b                   7.453(2)
_cell_length_c                   7.875(5)
_cell_angle_alpha                70.89(4)
_cell_angle_beta                 86.82(4)
_cell_angle_gamma                77.82(2)
_cell_volume                     262.61(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       50000
_cell_measurement_reflns_used    953
_cell_measurement_theta_min      4.30
_cell_measurement_theta_max      26.44

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.011
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             154
_exptl_absorpt_coefficient_mu    7.677
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.354
_exptl_absorpt_correction_T_max  0.398
_exptl_absorpt_process_details   
;
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467

Data were collected at room temperature and pressure of 0.05(5) GPa
 (50000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            953
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         4.30
_diffrn_reflns_theta_max         26.44
_reflns_number_total             155
_reflns_number_gt                134
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury (2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0244P)²+0.2640P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         155
_refine_ls_number_parameters     34
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0693
_refine_ls_wR_factor_gt          0.0656
_refine_ls_goodness_of_fit_ref   1.438
_refine_ls_restrained_S_all      1.605
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.1229(3) 0.3427(4) 0.8271(9) 0.0425(9) Uani 1 1 d U . .
N1 N 0.578(3) 0.684(4) 0.762(8) 0.040(4) Uiso 1 1 d . . .
H1 H 0.7251 0.6118 0.8232 0.048 Uiso 1 1 calc R . .
C2 C 0.383(3) 0.784(4) 0.838(9) 0.049(5) Uiso 1 1 d . . .
H2 H 0.4002 0.7721 0.9587 0.059 Uiso 1 1 calc R . .
C3 C 0.148(4) 0.908(5) 0.736(11) 0.035(6) Uiso 1 1 d . . .
H3 H 0.0070 0.9755 0.7901 0.041 Uiso 1 1 calc R . .
C4 C 0.120(4) 0.933(5) 0.546(11) 0.029(5) Uiso 1 1 d . . .
C5 C 0.323(3) 0.819(4) 0.471(8) 0.038(4) Uiso 1 1 d . . .
H5 H 0.3089 0.8261 0.3519 0.046 Uiso 1 1 calc R . .
C6 C 0.548(3) 0.694(4) 0.582(9) 0.025(4) Uiso 1 1 d . . .
H6 H 0.6827 0.6155 0.5343 0.030 Uiso 1 1 calc R . .

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
Br1 0.0399(9) 0.0433(10) 0.0415(17) -0.0137(11) 0.0003(11) -0.0024(6)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
N1 C2 1.32(3) . ?
N1 C6 1.41(9) . ?
C2 C3 1.40(6) . ?
C3 C4 1.45(12) . ?
C4 C5 1.39(3) . ?
C4 C4 1.42(10) 2_576 ?
C5 C6 1.40(6) . ?

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
C2 N1 C6 121(4) . . ?
N1 C2 C3 119(5) . . ?
C2 C3 C4 121(3) . . ?
C3 C4 C5 118(5) . . ?
C3 C4 C4 116(5) . 2_576 ?
C5 C4 C4 125(8) . 2_576 ?
C6 C5 C4 118(5) . . ?
N1 C6 C5 122(3) . . ?

_diffrn_measured_fraction_theta_max 0.145
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_full 0.145
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.050
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10G
_database_code_depnum_ccdc_archive 'CCDC 1452486'
_audit_update_record             
;
2016-02-10 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97

_chemical_name_systematic        'bipyridine hydrobromide'
_chemical_name_common            'bipyridine hydrobromide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Br2 N2'
_chemical_formula_sum            'C10 H10 Br2 N2'
_chemical_formula_weight         318.02

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8011(17)
_cell_length_b                   7.275(4)
_cell_length_c                   7.759(5)
_cell_angle_alpha                71.06(6)
_cell_angle_beta                 86.46(5)
_cell_angle_gamma                78.64(4)
_cell_volume                     251.3(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       100000
_cell_measurement_reflns_used    1865
_cell_measurement_theta_min      4.33
_cell_measurement_theta_max      34.93

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.101
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             154
_exptl_absorpt_coefficient_mu    8.022
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.289
_exptl_absorpt_correction_T_max  0.355
_exptl_absorpt_process_details   
;
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467

Data were collected at room temperature and pressure of 0.10(5) GPa
 (100000 kPa) with the crystal obtained by the in-situ high-pressure
 crystallization technique. Pressure was determined by monitoring 
the shift of the ruby R1-fluorescence line.
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1865
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_av_sigmaI/netI    0.0711
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         4.33
_diffrn_reflns_theta_max         34.93
_reflns_number_total             309
_reflns_number_gt                221
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury (2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0653P)²+0.4472P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         309
_refine_ls_number_parameters     34
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.1253(3) 0.3475(3) 0.8228(6) 0.072(7) Uani 1 1 d . . .
N1 N 0.576(3) 0.687(3) 0.768(6) 0.036(3) Uiso 1 1 d . . .
H1 H 0.7190 0.6135 0.8333 0.043 Uiso 1 1 calc R . .
C2 C 0.373(3) 0.792(3) 0.833(7) 0.038(3) Uiso 1 1 d . . .
H2 H 0.3807 0.7851 0.9545 0.046 Uiso 1 1 calc R . .
C3 C 0.140(3) 0.918(4) 0.724(8) 0.031(3) Uiso 1 1 d . . .
H3 H 0.0006 0.9936 0.7741 0.037 Uiso 1 1 calc R . .
C4 C 0.121(3) 0.927(3) 0.560(8) 0.029(3) Uiso 1 1 d . . .
C5 C 0.330(3) 0.809(3) 0.492(7) 0.036(3) Uiso 1 1 d . . .
H5 H 0.3104 0.8079 0.3736 0.043 Uiso 1 1 calc R . .
C6 C 0.550(3) 0.700(3) 0.585(8) 0.028(3) Uiso 1 1 d . . .
H6 H 0.6924 0.6305 0.5315 0.034 Uiso 1 1 calc R . .

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
Br1 0.0325(9) 0.054(3) 0.14(2) -0.056(7) 0.006(4) -0.0040(14)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
N1 C2 1.30(2) . ?
N1 C6 1.40(8) . ?
C2 C3 1.42(5) . ?
C3 C4 1.26(8) . ?
C4 C5 1.38(2) . ?
C4 C4 1.53(8) 2_576 ?
C5 C6 1.29(5) . ?

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
C2 N1 C6 117(3) . . ?
N1 C2 C3 122(4) . . ?
C4 C3 C2 120(2) . . ?
C3 C4 C5 118(4) . . ?
C3 C4 C4 120(3) . 2_576 ?
C5 C4 C4 122(6) . 2_576 ?
C4 C5 C6 123(4) . . ?
N1 C6 C5 120(2) . . ?

_diffrn_measured_fraction_theta_max 0.140
_diffrn_reflns_theta_full        34.93
_diffrn_measured_fraction_theta_full 0.140
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.088
#END
