# Electronic Supplementary Material (ESI) for ChemComm.
# 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_E1
_database_code_depnum_ccdc_archive 'CCDC 1472664'
_audit_update_record             
;
2016-05-16 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        "4,4'-Bipyridine; 3,5-diiodosalicylic acid"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 I2 N O3'
_chemical_formula_weight         467.99

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.60(3)
_cell_length_b                   4.372(6)
_cell_length_c                   34.30(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.444(15)
_cell_angle_gamma                90
_cell_volume                     2617(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2434
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      33.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.376
_exptl_crystal_F_000             1736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    4.805
_shelx_estimated_absorpt_T_min   0.596
_shelx_estimated_absorpt_T_max   0.620
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.629

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            5095
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_av_R_equivalents  0.0976
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.197
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2239
_reflns_number_gt                1987
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-14 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-14 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1190P)²+63.0134P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2239
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.2213
_refine_ls_wR_factor_gt          0.1946
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_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_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
C001 C -0.0416(7) 1.598(3) 0.0686(3) 0.022(2) Uani 1 1 d . . . . .
H001 H -0.0228 1.5313 0.0944 0.027 Uiso 1 1 calc R U . . .
C002 C -0.2442(6) 0.833(3) 0.1285(3) 0.019(2) Uani 1 1 d . . . . .
C005 C -0.0210(7) 1.899(3) 0.0112(3) 0.023(2) Uani 1 1 d . . . . .
C007 C -0.2072(7) 0.540(3) 0.1865(3) 0.019(2) Uani 1 1 d . . . . .
C008 C 0.0032(6) 1.794(3) 0.0491(3) 0.019(2) Uani 1 1 d . . . . .
H008 H 0.0516 1.8583 0.0620 0.023 Uiso 1 1 calc R U . . .
C009 C -0.3212(7) 0.760(3) 0.1305(3) 0.022(2) Uani 1 1 d . . . . .
C010 C -0.1892(7) 0.716(3) 0.1563(3) 0.025(3) Uani 1 1 d . . . . .
H010 H -0.1369 0.7579 0.1544 0.030 Uiso 1 1 calc R U . . .
C011 C -0.3387(6) 0.578(3) 0.1618(3) 0.018(2) Uani 1 1 d . . . . .
C012 C -0.0952(7) 1.798(3) -0.0040(3) 0.026(3) Uani 1 1 d . . . . .
H012 H -0.1167 1.8649 -0.0294 0.032 Uiso 1 1 calc R U . . .
C014 C -0.2266(7) 1.040(3) 0.0958(3) 0.024(3) Uani 1 1 d . . . . .
C015 C -0.2844(7) 0.467(3) 0.1894(3) 0.024(2) Uani 1 1 d . . . . .
H015 H -0.2976 0.3425 0.2102 0.028 Uiso 1 1 calc R U . . .
C016 C -0.1373(7) 1.606(3) 0.0165(4) 0.025(3) Uani 1 1 d . . . . .
H016 H -0.1872 1.5455 0.0052 0.030 Uiso 1 1 calc R U . . .
N1 N -0.1084(6) 1.503(2) 0.0524(3) 0.021(2) Uani 1 1 d . . . . .
O1 O -0.3790(5) 0.863(3) 0.1029(3) 0.035(2) Uani 1 1 d . . . . .
H1 H -0.3603 0.9713 0.0863 0.053 Uiso 1 1 calc R U . . .
O2 O -0.2753(6) 1.136(2) 0.0703(3) 0.033(2) Uani 1 1 d . . . . .
O3 O -0.1544(5) 1.109(2) 0.0980(2) 0.0274(19) Uani 1 1 d . . . . .
H3 H -0.1476 1.2257 0.0793 0.041 Uiso 1 1 calc R U . . .
I1 I -0.12268(5) 0.3687(2) 0.22970(2) 0.0305(3) Uani 1 1 d . . . . .
I2 I -0.45585(4) 0.5020(2) 0.16758(2) 0.0313(3) Uani 1 1 d . . . . .


_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
C001 N1 1.302(16) . ?
C001 C008 1.395(18) . ?
C001 H001 0.9500 . ?
C002 C010 1.368(16) . ?
C002 C009 1.403(17) . ?
C002 C014 1.504(16) . ?
C005 C008 1.391(16) . ?
C005 C012 1.414(18) . ?
C005 C005 1.44(2) 5_595 ?
C007 C010 1.360(16) . ?
C007 C015 1.411(17) . ?
C007 I1 2.096(11) . ?
C008 H008 0.9500 . ?
C009 O1 1.375(14) . ?
C009 C011 1.402(15) . ?
C010 H010 0.9500 . ?
C011 C015 1.345(17) . ?
C011 I2 2.122(12) . ?
C012 C016 1.371(18) . ?
C012 H012 0.9500 . ?
C014 O2 1.220(16) . ?
C014 O3 1.298(16) . ?
C015 H015 0.9500 . ?
C016 N1 1.350(16) . ?
C016 H016 0.9500 . ?
O1 H1 0.8400 . ?
O3 H3 0.8400 . ?

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
N1 C001 C008 121.8(10) . . ?
N1 C001 H001 119.1 . . ?
C008 C001 H001 119.1 . . ?
C010 C002 C009 118.7(11) . . ?
C010 C002 C014 123.3(11) . . ?
C009 C002 C014 117.9(10) . . ?
C008 C005 C012 113.5(11) . . ?
C008 C005 C005 125.8(15) . 5_595 ?
C012 C005 C005 120.6(14) . 5_595 ?
C010 C007 C015 120.1(11) . . ?
C010 C007 I1 121.8(9) . . ?
C015 C007 I1 118.1(8) . . ?
C005 C008 C001 121.8(11) . . ?
C005 C008 H008 119.1 . . ?
C001 C008 H008 119.1 . . ?
O1 C009 C011 119.9(11) . . ?
O1 C009 C002 121.6(10) . . ?
C011 C009 C002 118.5(10) . . ?
C007 C010 C002 122.0(12) . . ?
C007 C010 H010 119.0 . . ?
C002 C010 H010 119.0 . . ?
C015 C011 C009 122.4(11) . . ?
C015 C011 I2 119.3(8) . . ?
C009 C011 I2 118.2(8) . . ?
C016 C012 C005 122.5(11) . . ?
C016 C012 H012 118.8 . . ?
C005 C012 H012 118.8 . . ?
O2 C014 O3 123.5(11) . . ?
O2 C014 C002 123.3(11) . . ?
O3 C014 C002 113.2(10) . . ?
C011 C015 C007 118.2(10) . . ?
C011 C015 H015 120.9 . . ?
C007 C015 H015 120.9 . . ?
N1 C016 C012 120.5(12) . . ?
N1 C016 H016 119.7 . . ?
C012 C016 H016 119.7 . . ?
C001 N1 C016 119.7(10) . . ?
C009 O1 H1 109.5 . . ?
C014 O3 H3 109.5 . . ?

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
C012 C005 C008 C001 2.5(17) . . . . ?
C005 C005 C008 C001 -179.8(15) 5_595 . . . ?
N1 C001 C008 C005 -0.1(19) . . . . ?
C010 C002 C009 O1 -178.1(12) . . . . ?
C014 C002 C009 O1 2.4(18) . . . . ?
C010 C002 C009 C011 2.2(18) . . . . ?
C014 C002 C009 C011 -177.3(11) . . . . ?
C015 C007 C010 C002 1.8(19) . . . . ?
I1 C007 C010 C002 -178.7(9) . . . . ?
C009 C002 C010 C007 -2.5(19) . . . . ?
C014 C002 C010 C007 177.0(11) . . . . ?
O1 C009 C011 C015 179.0(12) . . . . ?
C002 C009 C011 C015 -1.3(18) . . . . ?
O1 C009 C011 I2 -5.3(16) . . . . ?
C002 C009 C011 I2 174.4(9) . . . . ?
C008 C005 C012 C016 -2.0(19) . . . . ?
C005 C005 C012 C016 -179.9(15) 5_595 . . . ?
C010 C002 C014 O2 177.4(13) . . . . ?
C009 C002 C014 O2 -3.1(18) . . . . ?
C010 C002 C014 O3 -3.5(17) . . . . ?
C009 C002 C014 O3 176.0(11) . . . . ?
C009 C011 C015 C007 0.5(18) . . . . ?
I2 C011 C015 C007 -175.2(9) . . . . ?
C010 C007 C015 C011 -0.7(18) . . . . ?
I1 C007 C015 C011 179.7(9) . . . . ?
C005 C012 C016 N1 -1(2) . . . . ?
C008 C001 N1 C016 -2.9(18) . . . . ?
C012 C016 N1 C001 3.4(19) . . . . ?

_refine_diff_density_max         1.144
_refine_diff_density_min         -1.533
_refine_diff_density_rms         0.364

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method THF
####################################################################### 
# 
# 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_E2
_database_code_depnum_ccdc_archive 'CCDC 1472665'
_audit_update_record             
;
2016-05-16 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        "4,4'-Bipyridine; 3,5-dichlorosalicylic acid"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 Cl4 N2 O6'
_chemical_formula_weight         570.19

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   3.795(9)
_cell_length_b                   14.70(3)
_cell_length_c                   21.40(5)
_cell_angle_alpha                80.70(5)
_cell_angle_beta                 89.35(6)
_cell_angle_gamma                89.09(5)
_cell_volume                     1178(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2192
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      32.9

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             580
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.549
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.612

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            10202
_diffrn_reflns_av_unetI/netI     0.1594
_diffrn_reflns_av_R_equivalents  0.1494
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         0.964
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4379
_reflns_number_gt                2547
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-14 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-14 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1347P)²+1.5968P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4379
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1611
_refine_ls_R_factor_gt           0.0979
_refine_ls_wR_factor_ref         0.3050
_refine_ls_wR_factor_gt          0.2310
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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_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
C004 C 1.8659(19) -0.3442(5) 0.6753(3) 0.0249(16) Uani 1 1 d . . . . .
C005 C 1.6018(18) -0.2957(5) 0.5719(3) 0.0207(15) Uani 1 1 d . . . . .
C006 C 1.7099(19) -0.2733(5) 0.6309(4) 0.0245(16) Uani 1 1 d . . . . .
C007 C 1.9131(18) -0.4337(5) 0.6609(3) 0.0240(16) Uani 1 1 d . . . . .
H007 H 2.0158 -0.4808 0.6911 0.029 Uiso 1 1 calc R U . . .
C008 C 1.6524(18) -0.3859(5) 0.5580(3) 0.0224(16) Uani 1 1 d . . . . .
H008 H 1.5790 -0.4001 0.5184 0.027 Uiso 1 1 calc R U . . .
C009 C 1.429(2) -0.2217(6) 0.5245(4) 0.0313(18) Uani 1 1 d . . . . .
C010 C 1.8083(19) -0.4533(5) 0.6018(3) 0.0244(16) Uani 1 1 d . . . . .
C014 C -0.2827(18) 0.2957(5) -0.1440(3) 0.0247(16) Uani 1 1 d . . . . .
C015 C -0.1591(19) 0.3089(5) -0.0829(4) 0.0269(17) Uani 1 1 d . . . . .
C016 C -0.0090(18) 0.2287(5) -0.0388(3) 0.0238(16) Uani 1 1 d . . . . .
C017 C -0.4150(19) 0.3716(5) -0.1850(3) 0.0227(16) Uani 1 1 d . . . . .
C018 C -0.4302(18) 0.4597(5) -0.1682(3) 0.0260(17) Uani 1 1 d . . . . .
H018 H -0.5178 0.5106 -0.1972 0.031 Uiso 1 1 calc R U . . .
C019 C -0.3157(18) 0.4717(5) -0.1088(4) 0.0234(16) Uani 1 1 d . . . . .
C020 C -0.1813(19) 0.3977(5) -0.0651(4) 0.0270(17) Uani 1 1 d . . . . .
H020 H -0.1067 0.4071 -0.0244 0.032 Uiso 1 1 calc R U . . .
C021 C 0.6403(17) 0.0258(5) 0.2136(4) 0.0233(16) Uani 1 1 d . . . . .
C022 C 0.7698(17) -0.0294(5) 0.2742(3) 0.0208(15) Uani 1 1 d . . . . .
C025 C 0.523(2) 0.0434(5) 0.1004(4) 0.0301(18) Uani 1 1 d . . . . .
H025 H 0.5328 0.0185 0.0621 0.036 Uiso 1 1 calc R U . . .
C026 C 0.6477(19) -0.0104(5) 0.1558(3) 0.0261(17) Uani 1 1 d . . . . .
H026 H 0.7367 -0.0710 0.1548 0.031 Uiso 1 1 calc R U . . .
C027 C 0.5094(19) 0.1163(5) 0.2107(4) 0.0258(17) Uani 1 1 d . . . . .
H027 H 0.5022 0.1444 0.2477 0.031 Uiso 1 1 calc R U . . .
C028 C 0.3894(19) 0.1650(6) 0.1529(4) 0.0295(18) Uani 1 1 d . . . . .
H028 H 0.3026 0.2262 0.1516 0.035 Uiso 1 1 calc R U . . .
C029 C 0.8836(18) 0.0136(5) 0.3245(3) 0.0265(17) Uani 1 1 d . . . . .
H029 H 0.8769 0.0789 0.3208 0.032 Uiso 1 1 calc R U . . .
C030 C 0.917(2) -0.1743(5) 0.3387(4) 0.0313(18) Uani 1 1 d . . . . .
H030 H 0.9305 -0.2396 0.3435 0.038 Uiso 1 1 calc R U . . .
C031 C 1.006(2) -0.0405(5) 0.3796(4) 0.0303(18) Uani 1 1 d . . . . .
H031 H 1.0770 -0.0109 0.4136 0.036 Uiso 1 1 calc R U . . .
C032 C 0.782(2) -0.1252(5) 0.2819(4) 0.0306(18) Uani 1 1 d . . . . .
H032 H 0.7006 -0.1567 0.2495 0.037 Uiso 1 1 calc R U . . .
N1 N 1.0273(16) -0.1328(5) 0.3866(3) 0.0307(15) Uani 1 1 d . . . . .
N2 N 0.3923(17) 0.1283(4) 0.0990(3) 0.0286(15) Uani 1 1 d . . . . .
O1 O 1.3316(14) -0.2486(4) 0.4720(2) 0.0340(14) Uani 1 1 d . . . . .
H1 H 1.2367 -0.2041 0.4482 0.051 Uiso 1 1 calc R U . . .
O2 O 1.3825(15) -0.1424(4) 0.5367(3) 0.0372(14) Uani 1 1 d . . . . .
O3 O -0.0075(16) 0.1493(4) -0.0533(3) 0.0407(15) Uani 1 1 d . . . . .
O4 O 0.1181(15) 0.2490(4) 0.0132(2) 0.0360(14) Uani 1 1 d . . . . .
H4 H 0.1976 0.2009 0.0355 0.054 Uiso 1 1 calc R U . . .
O5 O 1.6663(14) -0.1882(3) 0.6458(3) 0.0323(13) Uani 1 1 d . . . . .
H5 H 1.5718 -0.1535 0.6153 0.048 Uiso 1 1 calc R U . . .
O6 O -0.2792(15) 0.2112(4) -0.1621(3) 0.0353(14) Uani 1 1 d . . . . .
H6 H -0.1939 0.1721 -0.1330 0.053 Uiso 1 1 calc R U . . .
Cl1 Cl 2.0048(5) -0.31964(14) 0.74796(9) 0.0333(5) Uani 1 1 d . . . . .
Cl2 Cl -0.5535(5) 0.35786(14) -0.26107(9) 0.0312(5) Uani 1 1 d . . . . .
Cl3 Cl 1.8783(5) -0.56370(13) 0.58505(9) 0.0331(5) Uani 1 1 d . . . . .
Cl4 Cl -0.3497(6) 0.57903(14) -0.08493(10) 0.0386(6) Uani 1 1 d . . . . .


_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
C004 C007 1.406(10) . ?
C004 C006 1.419(10) . ?
C004 Cl1 1.742(8) . ?
C005 C008 1.415(10) . ?
C005 C006 1.422(10) . ?
C005 C009 1.509(10) . ?
C006 O5 1.347(9) . ?
C007 C010 1.404(10) . ?
C007 H007 0.9500 . ?
C008 C010 1.381(10) . ?
C008 H008 0.9500 . ?
C009 O2 1.246(10) . ?
C009 O1 1.308(10) . ?
C010 Cl3 1.733(8) . ?
C014 O6 1.360(9) . ?
C014 C017 1.395(10) . ?
C014 C015 1.437(11) . ?
C015 C020 1.418(11) . ?
C015 C016 1.496(10) . ?
C016 O3 1.256(9) . ?
C016 O4 1.298(9) . ?
C017 C018 1.398(10) . ?
C017 Cl2 1.760(8) . ?
C018 C019 1.387(11) . ?
C018 H018 0.9500 . ?
C019 C020 1.408(10) . ?
C019 Cl4 1.737(8) . ?
C020 H020 0.9500 . ?
C021 C027 1.405(10) . ?
C021 C026 1.425(10) . ?
C021 C022 1.497(10) . ?
C022 C032 1.391(11) . ?
C022 C029 1.408(10) . ?
C025 N2 1.331(10) . ?
C025 C026 1.397(10) . ?
C025 H025 0.9500 . ?
C026 H026 0.9500 . ?
C027 C028 1.401(10) . ?
C027 H027 0.9500 . ?
C028 N2 1.349(10) . ?
C028 H028 0.9500 . ?
C029 C031 1.391(10) . ?
C029 H029 0.9500 . ?
C030 N1 1.349(10) . ?
C030 C032 1.408(11) . ?
C030 H030 0.9500 . ?
C031 N1 1.343(10) . ?
C031 H031 0.9500 . ?
C032 H032 0.9500 . ?
O1 H1 0.8400 . ?
O4 H4 0.8400 . ?
O5 H5 0.8400 . ?
O6 H6 0.8400 . ?

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
C007 C004 C006 120.7(7) . . ?
C007 C004 Cl1 119.8(5) . . ?
C006 C004 Cl1 119.5(6) . . ?
C008 C005 C006 120.7(6) . . ?
C008 C005 C009 120.5(7) . . ?
C006 C005 C009 118.8(7) . . ?
O5 C006 C004 119.7(7) . . ?
O5 C006 C005 122.3(6) . . ?
C004 C006 C005 117.9(7) . . ?
C004 C007 C010 120.0(6) . . ?
C004 C007 H007 120.0 . . ?
C010 C007 H007 120.0 . . ?
C010 C008 C005 120.1(7) . . ?
C010 C008 H008 120.0 . . ?
C005 C008 H008 120.0 . . ?
O2 C009 O1 124.5(7) . . ?
O2 C009 C005 120.7(7) . . ?
O1 C009 C005 114.8(7) . . ?
C008 C010 C007 120.5(7) . . ?
C008 C010 Cl3 120.7(6) . . ?
C007 C010 Cl3 118.8(5) . . ?
O6 C014 C017 119.5(7) . . ?
O6 C014 C015 121.8(7) . . ?
C017 C014 C015 118.7(7) . . ?
C020 C015 C014 119.7(6) . . ?
C020 C015 C016 120.8(7) . . ?
C014 C015 C016 119.5(7) . . ?
O3 C016 O4 124.7(7) . . ?
O3 C016 C015 120.5(7) . . ?
O4 C016 C015 114.7(7) . . ?
C014 C017 C018 121.8(7) . . ?
C014 C017 Cl2 119.5(5) . . ?
C018 C017 Cl2 118.6(5) . . ?
C019 C018 C017 119.2(7) . . ?
C019 C018 H018 120.4 . . ?
C017 C018 H018 120.4 . . ?
C018 C019 C020 121.7(7) . . ?
C018 C019 Cl4 120.5(6) . . ?
C020 C019 Cl4 117.7(6) . . ?
C019 C020 C015 118.8(7) . . ?
C019 C020 H020 120.6 . . ?
C015 C020 H020 120.6 . . ?
C027 C021 C026 116.5(7) . . ?
C027 C021 C022 121.8(7) . . ?
C026 C021 C022 121.7(7) . . ?
C032 C022 C029 118.4(7) . . ?
C032 C022 C021 120.3(7) . . ?
C029 C022 C021 121.4(7) . . ?
N2 C025 C026 122.7(8) . . ?
N2 C025 H025 118.7 . . ?
C026 C025 H025 118.7 . . ?
C025 C026 C021 119.7(7) . . ?
C025 C026 H026 120.1 . . ?
C021 C026 H026 120.1 . . ?
C028 C027 C021 119.7(7) . . ?
C028 C027 H027 120.2 . . ?
C021 C027 H027 120.2 . . ?
N2 C028 C027 122.6(8) . . ?
N2 C028 H028 118.7 . . ?
C027 C028 H028 118.7 . . ?
C031 C029 C022 119.3(7) . . ?
C031 C029 H029 120.3 . . ?
C022 C029 H029 120.3 . . ?
N1 C030 C032 123.0(7) . . ?
N1 C030 H030 118.5 . . ?
C032 C030 H030 118.5 . . ?
N1 C031 C029 122.7(7) . . ?
N1 C031 H031 118.7 . . ?
C029 C031 H031 118.7 . . ?
C022 C032 C030 118.5(7) . . ?
C022 C032 H032 120.8 . . ?
C030 C032 H032 120.8 . . ?
C031 N1 C030 118.2(7) . . ?
C025 N2 C028 118.8(7) . . ?
C009 O1 H1 109.5 . . ?
C016 O4 H4 109.5 . . ?
C006 O5 H5 109.5 . . ?
C014 O6 H6 109.5 . . ?

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
C007 C004 C006 O5 179.8(6) . . . . ?
Cl1 C004 C006 O5 -1.0(10) . . . . ?
C007 C004 C006 C005 0.4(11) . . . . ?
Cl1 C004 C006 C005 179.6(5) . . . . ?
C008 C005 C006 O5 179.9(6) . . . . ?
C009 C005 C006 O5 -0.5(10) . . . . ?
C008 C005 C006 C004 -0.7(10) . . . . ?
C009 C005 C006 C004 178.9(7) . . . . ?
C006 C004 C007 C010 0.6(11) . . . . ?
Cl1 C004 C007 C010 -178.6(6) . . . . ?
C006 C005 C008 C010 0.0(10) . . . . ?
C009 C005 C008 C010 -179.6(7) . . . . ?
C008 C005 C009 O2 179.6(7) . . . . ?
C006 C005 C009 O2 0.0(11) . . . . ?
C008 C005 C009 O1 0.9(10) . . . . ?
C006 C005 C009 O1 -178.7(6) . . . . ?
C005 C008 C010 C007 1.0(11) . . . . ?
C005 C008 C010 Cl3 -179.0(5) . . . . ?
C004 C007 C010 C008 -1.3(11) . . . . ?
C004 C007 C010 Cl3 178.7(6) . . . . ?
O6 C014 C015 C020 -177.4(7) . . . . ?
C017 C014 C015 C020 1.4(11) . . . . ?
O6 C014 C015 C016 2.5(11) . . . . ?
C017 C014 C015 C016 -178.7(7) . . . . ?
C020 C015 C016 O3 176.1(7) . . . . ?
C014 C015 C016 O3 -3.8(11) . . . . ?
C020 C015 C016 O4 -4.8(10) . . . . ?
C014 C015 C016 O4 175.3(6) . . . . ?
O6 C014 C017 C018 178.9(6) . . . . ?
C015 C014 C017 C018 0.0(11) . . . . ?
O6 C014 C017 Cl2 -3.3(10) . . . . ?
C015 C014 C017 Cl2 177.8(5) . . . . ?
C014 C017 C018 C019 -1.0(11) . . . . ?
Cl2 C017 C018 C019 -178.8(5) . . . . ?
C017 C018 C019 C020 0.6(10) . . . . ?
C017 C018 C019 Cl4 -177.0(5) . . . . ?
C018 C019 C020 C015 0.8(11) . . . . ?
Cl4 C019 C020 C015 178.4(5) . . . . ?
C014 C015 C020 C019 -1.8(11) . . . . ?
C016 C015 C020 C019 178.3(6) . . . . ?
C027 C021 C022 C032 157.6(7) . . . . ?
C026 C021 C022 C032 -23.2(10) . . . . ?
C027 C021 C022 C029 -22.7(10) . . . . ?
C026 C021 C022 C029 156.5(7) . . . . ?
N2 C025 C026 C021 -0.8(12) . . . . ?
C027 C021 C026 C025 -0.9(10) . . . . ?
C022 C021 C026 C025 179.9(7) . . . . ?
C026 C021 C027 C028 1.1(10) . . . . ?
C022 C021 C027 C028 -179.6(7) . . . . ?
C021 C027 C028 N2 0.3(11) . . . . ?
C032 C022 C029 C031 0.5(11) . . . . ?
C021 C022 C029 C031 -179.2(7) . . . . ?
C022 C029 C031 N1 1.4(12) . . . . ?
C029 C022 C032 C030 -1.9(11) . . . . ?
C021 C022 C032 C030 177.8(7) . . . . ?
N1 C030 C032 C022 1.6(12) . . . . ?
C029 C031 N1 C030 -1.7(11) . . . . ?
C032 C030 N1 C031 0.2(12) . . . . ?
C026 C025 N2 C028 2.2(11) . . . . ?
C027 C028 N2 C025 -1.9(11) . . . . ?

_refine_diff_density_max         0.669
_refine_diff_density_min         -0.754
_refine_diff_density_rms         0.153

_shelxl_version_number           2014-3


# start Validation Reply Form
_vrf_PLAT340_E2                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01091 Ang.  
RESPONSE: The above alert is generated due to poor quality of the crystal.  
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method THF
####################################################################### 
# 
# 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_E3
_database_code_depnum_ccdc_archive 'CCDC 1472666'
_audit_update_record             
;
2016-05-16 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        "4,4'-Bipyridine; 3,5-dibromophenol"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 Br2 N O'
_chemical_formula_weight         330.00

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   4.183(3)
_cell_length_b                   8.769(7)
_cell_length_c                   15.366(12)
_cell_angle_alpha                94.10(3)
_cell_angle_beta                 95.78(3)
_cell_angle_gamma                99.68(3)
_cell_volume                     550.5(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1721
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      33.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.991
_exptl_crystal_F_000             318
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    7.332
_shelx_estimated_absorpt_T_min   0.473
_shelx_estimated_absorpt_T_max   0.473
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.444

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            5227
_diffrn_reflns_av_unetI/netI     0.1051
_diffrn_reflns_av_R_equivalents  0.1234
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.337
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2163
_reflns_number_gt                1750
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-14 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-14 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0839P)²+0.1860P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2163
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1890
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_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_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
C2 C 1.1306(15) -0.0890(6) 0.8834(4) 0.0363(14) Uani 1 1 d . . . . .
H2 H 1.2763 -0.0963 0.9339 0.044 Uiso 1 1 calc R U . . .
C3 C 0.0713(14) 0.4405(7) 0.5239(4) 0.0322(12) Uani 1 1 d . . . . .
C4 C 1.0728(15) 0.0530(6) 0.8566(4) 0.0315(12) Uani 1 1 d . . . . .
C5 C 0.259(2) 0.1948(9) 0.5282(5) 0.0532(19) Uani 1 1 d . . . . .
H5 H 0.2946 0.1027 0.4970 0.064 Uiso 1 1 calc R U . . .
C6 C 0.8650(14) 0.0671(6) 0.7848(4) 0.0337(12) Uani 1 1 d . . . . .
H6 H 0.8314 0.1668 0.7695 0.040 Uiso 1 1 calc R U . . .
C8 C 0.7526(15) -0.2112(7) 0.7594(4) 0.0358(13) Uani 1 1 d . . . . .
H8 H 0.6403 -0.3034 0.7260 0.043 Uiso 1 1 calc R U . . .
C9 C 0.9615(15) -0.2195(6) 0.8315(4) 0.0340(13) Uani 1 1 d . . . . .
C10 C 0.2951(18) 0.3460(8) 0.6561(4) 0.0482(17) Uani 1 1 d . . . . .
H10 H 0.3570 0.3632 0.7177 0.058 Uiso 1 1 calc R U . . .
C11 C 0.1617(16) 0.4592(7) 0.6147(4) 0.0413(14) Uani 1 1 d . . . . .
H11 H 0.1312 0.5501 0.6481 0.050 Uiso 1 1 calc R U . . .
C12 C 0.7035(15) -0.0654(7) 0.7345(4) 0.0347(13) Uani 1 1 d . . . . .
C15 C 0.1227(17) 0.3030(7) 0.4807(4) 0.0440(15) Uani 1 1 d . . . . .
H15 H 0.0651 0.2828 0.4191 0.053 Uiso 1 1 calc R U . . .
N1 N 0.3426(14) 0.2137(7) 0.6148(4) 0.0468(13) Uani 1 1 d . . . . .
O1 O 0.4899(13) -0.0645(6) 0.6623(3) 0.0539(13) Uani 1 1 d . . . . .
H1 H 0.4732 0.0276 0.6538 0.081 Uiso 1 1 calc R U . . .
Br1 Br 1.30595(17) 0.23626(7) 0.92383(4) 0.0464(3) Uani 1 1 d . . . . .
Br2 Br 1.02797(19) -0.41886(7) 0.86465(5) 0.0485(3) Uani 1 1 d . . . . .


_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
C2 C9 1.389(8) . ?
C2 C4 1.391(8) . ?
C2 H2 0.9500 . ?
C3 C15 1.394(9) . ?
C3 C11 1.399(9) . ?
C3 C3 1.488(12) 2_566 ?
C4 C6 1.360(8) . ?
C4 Br1 1.906(6) . ?
C5 N1 1.331(9) . ?
C5 C15 1.400(10) . ?
C5 H5 0.9500 . ?
C6 C12 1.381(8) . ?
C6 H6 0.9500 . ?
C8 C9 1.355(9) . ?
C8 C12 1.403(9) . ?
C8 H8 0.9500 . ?
C9 Br2 1.911(6) . ?
C10 N1 1.337(9) . ?
C10 C11 1.381(10) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 O1 1.354(8) . ?
C15 H15 0.9500 . ?
O1 H1 0.8400 . ?

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
C9 C2 C4 115.6(5) . . ?
C9 C2 H2 122.2 . . ?
C4 C2 H2 122.2 . . ?
C15 C3 C11 115.8(6) . . ?
C15 C3 C3 121.8(7) . 2_566 ?
C11 C3 C3 122.4(7) . 2_566 ?
C6 C4 C2 123.5(5) . . ?
C6 C4 Br1 119.0(4) . . ?
C2 C4 Br1 117.5(4) . . ?
N1 C5 C15 123.6(7) . . ?
N1 C5 H5 118.2 . . ?
C15 C5 H5 118.2 . . ?
C4 C6 C12 119.1(5) . . ?
C4 C6 H6 120.5 . . ?
C12 C6 H6 120.5 . . ?
C9 C8 C12 119.4(5) . . ?
C9 C8 H8 120.3 . . ?
C12 C8 H8 120.3 . . ?
C8 C9 C2 122.9(6) . . ?
C8 C9 Br2 119.1(4) . . ?
C2 C9 Br2 117.9(4) . . ?
N1 C10 C11 124.0(6) . . ?
N1 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
C10 C11 C3 120.2(6) . . ?
C10 C11 H11 119.9 . . ?
C3 C11 H11 119.9 . . ?
O1 C12 C6 123.9(6) . . ?
O1 C12 C8 116.8(6) . . ?
C6 C12 C8 119.4(5) . . ?
C3 C15 C5 119.9(6) . . ?
C3 C15 H15 120.0 . . ?
C5 C15 H15 120.0 . . ?
C5 N1 C10 116.4(6) . . ?
C12 O1 H1 109.5 . . ?

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
C9 C2 C4 C6 0.2(9) . . . . ?
C9 C2 C4 Br1 -178.6(4) . . . . ?
C2 C4 C6 C12 -0.8(10) . . . . ?
Br1 C4 C6 C12 178.0(4) . . . . ?
C12 C8 C9 C2 0.5(10) . . . . ?
C12 C8 C9 Br2 -179.8(4) . . . . ?
C4 C2 C9 C8 -0.1(9) . . . . ?
C4 C2 C9 Br2 -179.8(4) . . . . ?
N1 C10 C11 C3 -1.0(12) . . . . ?
C15 C3 C11 C10 0.5(10) . . . . ?
C3 C3 C11 C10 -179.6(7) 2_566 . . . ?
C4 C6 C12 O1 179.4(6) . . . . ?
C4 C6 C12 C8 1.2(9) . . . . ?
C9 C8 C12 O1 -179.5(6) . . . . ?
C9 C8 C12 C6 -1.1(9) . . . . ?
C11 C3 C15 C5 -0.4(10) . . . . ?
C3 C3 C15 C5 179.6(8) 2_566 . . . ?
N1 C5 C15 C3 0.9(12) . . . . ?
C15 C5 N1 C10 -1.3(12) . . . . ?
C11 C10 N1 C5 1.3(12) . . . . ?

_refine_diff_density_max         1.036
_refine_diff_density_min         -1.398
_refine_diff_density_rms         0.222

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method THF
####################################################################### 
# 
# 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_E4
_database_code_depnum_ccdc_archive 'CCDC 1472667'
_audit_update_record             
;
2016-05-16 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        'Pyrazine; 3,5-dichlorosalicylic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 Cl2 N O3'
_chemical_formula_weight         247.05

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   3.777(7)
_cell_length_b                   10.382(17)
_cell_length_c                   13.45(2)
_cell_angle_alpha                68.43(4)
_cell_angle_beta                 85.15(6)
_cell_angle_gamma                80.26(6)
_cell_volume                     483.3(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1530
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      33.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_F_000             250
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.654
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.641

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            4600
_diffrn_reflns_av_unetI/netI     0.1024
_diffrn_reflns_av_R_equivalents  0.1173
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.629
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1906
_reflns_number_gt                1556
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-14 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-14 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²+0.5384P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1906
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1349
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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_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
C004 C -0.2644(9) 0.1193(4) -0.4345(3) 0.0164(7) Uani 1 1 d . . . . .
H004 H -0.3279 0.0957 -0.4919 0.020 Uiso 1 1 calc R U . . .
C005 C -0.2178(9) 0.2555(4) -0.4512(3) 0.0161(7) Uani 1 1 d . . . . .
C006 C -0.0655(9) 0.1884(4) -0.2664(3) 0.0159(7) Uani 1 1 d . . . . .
C007 C -0.1208(9) 0.0501(4) -0.2465(3) 0.0172(8) Uani 1 1 d . . . . .
C008 C -0.2168(9) 0.0183(4) -0.3331(3) 0.0154(7) Uani 1 1 d . . . . .
C009 C -0.1159(9) 0.2908(4) -0.3688(3) 0.0164(7) Uani 1 1 d . . . . .
H009 H -0.0806 0.3841 -0.3818 0.020 Uiso 1 1 calc R U . . .
C010 C 0.0461(10) 0.2246(4) -0.1770(3) 0.0201(8) Uani 1 1 d . . . . .
C011 C 0.4873(10) 0.3628(4) 0.0334(3) 0.0226(8) Uani 1 1 d . . . . .
H011 H 0.4824 0.2648 0.0599 0.027 Uiso 1 1 calc R U . . .
C013 C 0.6214(10) 0.4222(4) 0.0970(3) 0.0212(8) Uani 1 1 d . . . . .
H013 H 0.7060 0.3635 0.1660 0.025 Uiso 1 1 calc R U . . .
N1 N 0.3653(8) 0.4410(3) -0.0640(3) 0.0211(7) Uani 1 1 d . . . . .
O1 O -0.0826(7) -0.0546(3) -0.1500(2) 0.0250(6) Uani 1 1 d . . . . .
H1 H -0.0243 -0.0237 -0.1051 0.037 Uiso 1 1 calc R U . . .
O2 O 0.0801(8) 0.1408(3) -0.0855(2) 0.0319(7) Uani 1 1 d . . . . .
O3 O 0.1069(7) 0.3558(3) -0.2067(2) 0.0252(6) Uani 1 1 d . . . . .
H3 H 0.1688 0.3700 -0.1535 0.038 Uiso 1 1 calc R U . . .
Cl1 Cl -0.2821(2) -0.15132(9) -0.31233(7) 0.0217(3) Uani 1 1 d . . . . .
Cl2 Cl -0.2896(2) 0.38377(9) -0.57824(7) 0.0228(3) Uani 1 1 d . . . . .


_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
C004 C008 1.385(5) . ?
C004 C005 1.388(5) . ?
C004 H004 0.9500 . ?
C005 C009 1.389(5) . ?
C005 Cl2 1.747(4) . ?
C006 C009 1.400(5) . ?
C006 C007 1.409(6) . ?
C006 C010 1.496(5) . ?
C007 O1 1.351(5) . ?
C007 C008 1.412(5) . ?
C008 Cl1 1.736(5) . ?
C009 H009 0.9500 . ?
C010 O2 1.220(5) . ?
C010 O3 1.325(5) . ?
C011 N1 1.335(5) . ?
C011 C013 1.391(6) . ?
C011 H011 0.9500 . ?
C013 N1 1.332(5) 2_665 ?
C013 H013 0.9500 . ?
N1 C013 1.332(5) 2_665 ?
O1 H1 0.8400 . ?
O3 H3 0.8400 . ?

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
C008 C004 C005 119.0(3) . . ?
C008 C004 H004 120.5 . . ?
C005 C004 H004 120.5 . . ?
C004 C005 C009 121.1(3) . . ?
C004 C005 Cl2 119.0(3) . . ?
C009 C005 Cl2 119.9(3) . . ?
C009 C006 C007 120.3(3) . . ?
C009 C006 C010 120.4(3) . . ?
C007 C006 C010 119.3(3) . . ?
O1 C007 C006 124.2(3) . . ?
O1 C007 C008 117.9(3) . . ?
C006 C007 C008 117.9(3) . . ?
C004 C008 C007 121.8(3) . . ?
C004 C008 Cl1 118.8(3) . . ?
C007 C008 Cl1 119.4(3) . . ?
C005 C009 C006 119.8(3) . . ?
C005 C009 H009 120.1 . . ?
C006 C009 H009 120.1 . . ?
O2 C010 O3 123.3(3) . . ?
O2 C010 C006 123.0(4) . . ?
O3 C010 C006 113.7(3) . . ?
N1 C011 C013 121.3(4) . . ?
N1 C011 H011 119.4 . . ?
C013 C011 H011 119.4 . . ?
N1 C013 C011 121.9(4) 2_665 . ?
N1 C013 H013 119.1 2_665 . ?
C011 C013 H013 119.1 . . ?
C013 N1 C011 116.8(3) 2_665 . ?
C007 O1 H1 109.5 . . ?
C010 O3 H3 109.5 . . ?

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
C008 C004 C005 C009 1.7(5) . . . . ?
C008 C004 C005 Cl2 -178.3(3) . . . . ?
C009 C006 C007 O1 -179.1(3) . . . . ?
C010 C006 C007 O1 0.6(5) . . . . ?
C009 C006 C007 C008 1.9(5) . . . . ?
C010 C006 C007 C008 -178.4(3) . . . . ?
C005 C004 C008 C007 -0.3(5) . . . . ?
C005 C004 C008 Cl1 179.0(3) . . . . ?
O1 C007 C008 C004 179.5(3) . . . . ?
C006 C007 C008 C004 -1.4(5) . . . . ?
O1 C007 C008 Cl1 0.1(4) . . . . ?
C006 C007 C008 Cl1 179.2(3) . . . . ?
C004 C005 C009 C006 -1.2(5) . . . . ?
Cl2 C005 C009 C006 178.7(3) . . . . ?
C007 C006 C009 C005 -0.6(5) . . . . ?
C010 C006 C009 C005 179.7(3) . . . . ?
C009 C006 C010 O2 177.0(3) . . . . ?
C007 C006 C010 O2 -2.7(6) . . . . ?
C009 C006 C010 O3 -3.4(5) . . . . ?
C007 C006 C010 O3 176.8(3) . . . . ?
N1 C011 C013 N1 0.0(6) . . . 2_665 ?
C013 C011 N1 C013 0.0(6) . . . 2_665 ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.111

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method MeOH
####################################################################### 
# 
# 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_E5
_database_code_depnum_ccdc_archive 'CCDC 1472668'
_audit_update_record             
;
2016-05-16 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        'Pyrazine; 3,5-diiodosalicylic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 I2 N O3'
_chemical_formula_weight         429.95

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.78(3)
_cell_length_b                   4.706(4)
_cell_length_c                   17.566(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.051(8)
_cell_angle_gamma                90
_cell_volume                     2284(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4171
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      33.7

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.501
_exptl_crystal_F_000             1576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.494
_shelx_estimated_absorpt_T_min   0.558
_shelx_estimated_absorpt_T_max   0.610
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.679

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            10048
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_av_R_equivalents  0.1433
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.474
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2243
_reflns_number_gt                2108
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-14 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-14 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0822P)²+0.0970P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2243
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_restrained_S_all      1.204
_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_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
C001 C -0.1789(2) -1.2489(14) 0.3249(3) 0.0192(12) Uani 1 1 d . . . . .
C004 C -0.1119(2) -0.9303(12) 0.3153(4) 0.0191(12) Uani 1 1 d . . . . .
C005 C -0.1091(2) -1.0170(12) 0.2387(3) 0.0201(12) Uani 1 1 d . . . . .
C007 C -0.1773(2) -1.3314(12) 0.2486(4) 0.0197(12) Uani 1 1 d . . . . .
H007 H -0.1994 -1.4630 0.2261 0.024 Uiso 1 1 calc R U . . .
C008 C -0.1470(2) -1.0507(12) 0.3564(4) 0.0195(12) Uani 1 1 d . . . . .
H008 H -0.1487 -0.9941 0.4067 0.023 Uiso 1 1 calc R U . . .
C009 C -0.1423(2) -1.2146(13) 0.2068(3) 0.0208(12) Uani 1 1 d . . . . .
C010 C -0.0784(2) -0.7100(12) 0.3483(3) 0.0187(12) Uani 1 1 d . . . . .
C013 C 0.0056(2) -0.1121(13) 0.4316(4) 0.0201(12) Uani 1 1 d . . . . .
H013 H 0.0102 -0.1847 0.3837 0.024 Uiso 1 1 calc R U . . .
C015 C 0.0344(2) 0.1102(13) 0.4610(4) 0.0204(12) Uani 1 1 d . . . . .
H015 H 0.0582 0.1816 0.4328 0.024 Uiso 1 1 calc R U . . .
N1 N -0.02852(19) -0.2251(10) 0.4703(3) 0.0184(10) Uani 1 1 d . . . . .
O1 O -0.04630(19) -0.6094(10) 0.3135(3) 0.0284(11) Uani 1 1 d . . . . .
O2 O -0.08535(16) -0.6365(9) 0.4184(3) 0.0219(9) Uani 1 1 d . . . . .
H2 H -0.0657 -0.5139 0.4337 0.033 Uiso 1 1 calc R U . . .
O3 O -0.07475(18) -0.9147(10) 0.1970(3) 0.0270(10) Uani 1 1 d . . . . .
H3 H -0.0577 -0.8008 0.2229 0.040 Uiso 1 1 calc R U . . .
I1 I -0.14361(2) -1.32258(9) 0.09006(2) 0.0269(2) Uani 1 1 d . . . . .
I2 I -0.23134(2) -1.42379(10) 0.38907(2) 0.0282(2) Uani 1 1 d . . . . .


_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
C001 C008 1.363(9) . ?
C001 C007 1.401(9) . ?
C001 I2 2.101(6) . ?
C004 C008 1.392(9) . ?
C004 C005 1.416(8) . ?
C004 C010 1.471(8) . ?
C005 O3 1.351(8) . ?
C005 C009 1.385(9) . ?
C007 C009 1.391(9) . ?
C007 H007 0.9300 . ?
C008 H008 0.9300 . ?
C009 I1 2.109(6) . ?
C010 O1 1.229(8) . ?
C010 O2 1.312(8) . ?
C013 N1 1.334(8) . ?
C013 C015 1.383(9) . ?
C013 H013 0.9300 . ?
C015 N1 1.347(8) 5_556 ?
C015 H015 0.9300 . ?
N1 C015 1.347(8) 5_556 ?
O2 H2 0.8200 . ?
O3 H3 0.8200 . ?

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
C008 C001 C007 119.5(6) . . ?
C008 C001 I2 120.6(5) . . ?
C007 C001 I2 119.9(5) . . ?
C008 C004 C005 119.1(6) . . ?
C008 C004 C010 122.0(6) . . ?
C005 C004 C010 118.8(6) . . ?
O3 C005 C009 119.9(5) . . ?
O3 C005 C004 121.6(6) . . ?
C009 C005 C004 118.5(6) . . ?
C009 C007 C001 119.4(6) . . ?
C009 C007 H007 120.3 . . ?
C001 C007 H007 120.3 . . ?
C001 C008 C004 122.0(6) . . ?
C001 C008 H008 119.0 . . ?
C004 C008 H008 119.0 . . ?
C005 C009 C007 121.6(6) . . ?
C005 C009 I1 119.8(4) . . ?
C007 C009 I1 118.4(5) . . ?
O1 C010 O2 123.5(6) . . ?
O1 C010 C004 122.5(6) . . ?
O2 C010 C004 114.0(5) . . ?
N1 C013 C015 121.7(6) . . ?
N1 C013 H013 119.2 . . ?
C015 C013 H013 119.2 . . ?
N1 C015 C013 121.2(6) 5_556 . ?
N1 C015 H015 119.4 5_556 . ?
C013 C015 H015 119.4 . . ?
C013 N1 C015 117.1(5) . 5_556 ?
C010 O2 H2 109.5 . . ?
C005 O3 H3 109.5 . . ?

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
C008 C004 C005 O3 -177.7(5) . . . . ?
C010 C004 C005 O3 3.9(9) . . . . ?
C008 C004 C005 C009 1.5(9) . . . . ?
C010 C004 C005 C009 -176.9(5) . . . . ?
C008 C001 C007 C009 1.6(9) . . . . ?
I2 C001 C007 C009 -179.8(5) . . . . ?
C007 C001 C008 C004 -1.3(9) . . . . ?
I2 C001 C008 C004 -179.8(4) . . . . ?
C005 C004 C008 C001 -0.3(9) . . . . ?
C010 C004 C008 C001 178.1(6) . . . . ?
O3 C005 C009 C007 178.0(5) . . . . ?
C004 C005 C009 C007 -1.1(9) . . . . ?
O3 C005 C009 I1 -6.4(8) . . . . ?
C004 C005 C009 I1 174.5(4) . . . . ?
C001 C007 C009 C005 -0.4(9) . . . . ?
C001 C007 C009 I1 -176.1(5) . . . . ?
C008 C004 C010 O1 177.5(6) . . . . ?
C005 C004 C010 O1 -4.2(9) . . . . ?
C008 C004 C010 O2 -1.1(8) . . . . ?
C005 C004 C010 O2 177.3(5) . . . . ?
N1 C013 C015 N1 -1.1(10) . . . 5_556 ?
C015 C013 N1 C015 1.1(10) . . . 5_556 ?

_refine_diff_density_max         1.891
_refine_diff_density_min         -1.355
_refine_diff_density_rms         0.295

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method MeOH
