# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1519858'
_audit_update_record             
;
2017-06-29 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H8 Cl I N4'
_chemical_formula_weight         334.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.5620(19)
_cell_length_b                   6.6530(13)
_cell_length_c                   17.748(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.05(3)
_cell_angle_gamma                90
_cell_volume                     1127.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.971
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.049
_shelx_estimated_absorpt_T_min   0.581
_shelx_estimated_absorpt_T_max   0.750
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.133
_diffrn_reflns_theta_max         25.374
_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             2062
_reflns_number_gt                1618
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0670P)²] 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         2062
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
I I 0.65909(4) -0.39477(6) 0.40315(2) 0.04364(19) Uani 1 1 d . . . . .
Cl Cl 0.89342(17) 0.2355(2) 0.42956(8) 0.0458(4) Uani 1 1 d . . . . .
N1 N 0.0158(6) 0.8679(7) 0.3561(3) 0.0428(13) Uani 1 1 d . . . . .
H1A H -0.0427 0.9363 0.3809 0.051 Uiso 1 1 calc R U . . .
C1 C 0.0768(6) 0.7038(10) 0.3814(3) 0.0422(15) Uani 1 1 d . . . . .
H1B H 0.0665 0.6442 0.4281 0.051 Uiso 1 1 calc R U . . .
N2 N 0.0556(6) 0.9183(7) 0.2862(3) 0.0468(14) Uani 1 1 d . . . . .
C2 C 0.1415(7) 0.7737(9) 0.2697(3) 0.0429(15) Uani 1 1 d . . . . .
H2B H 0.1865 0.7645 0.2246 0.052 Uiso 1 1 calc R U . . .
N3 N 0.1565(5) 0.6382(7) 0.3273(2) 0.0326(11) Uani 1 1 d . . . . .
C3 C 0.2392(6) 0.3414(9) 0.3734(3) 0.0379(14) Uani 1 1 d . . . . .
H3A H 0.1684 0.3501 0.4072 0.046 Uiso 1 1 calc R U . . .
N4 N 0.2505(5) 0.4772(8) 0.3242(3) 0.0372(12) Uani 1 1 d . . . . .
C4 C 0.3359(6) 0.1706(9) 0.3779(3) 0.0319(13) Uani 1 1 d . . . . .
C5 C 0.4478(7) 0.1558(10) 0.3310(3) 0.0407(15) Uani 1 1 d . . . . .
H5A H 0.4621 0.2550 0.2952 0.049 Uiso 1 1 calc R U . . .
C6 C 0.5381(7) -0.0081(9) 0.3378(3) 0.0383(14) Uani 1 1 d . . . . .
H6A H 0.6122 -0.0198 0.3062 0.046 Uiso 1 1 calc R U . . .
C7 C 0.5173(6) -0.1528(8) 0.3914(3) 0.0329(13) Uani 1 1 d . . . . .
C8 C 0.4068(6) -0.1407(9) 0.4382(3) 0.0371(14) Uani 1 1 d . . . . .
H8A H 0.3928 -0.2415 0.4732 0.044 Uiso 1 1 calc R U . . .
C9 C 0.3170(6) 0.0225(9) 0.4325(3) 0.0364(13) Uani 1 1 d . . . . .
H9A H 0.2442 0.0338 0.4650 0.044 Uiso 1 1 calc R U . . .


_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
I C7 2.108(6) . ?
N1 C1 1.306(8) . ?
N1 N2 1.359(7) . ?
N1 H1A 0.8600 . ?
C1 N3 1.331(7) . ?
C1 H1B 0.9300 . ?
N2 C2 1.308(8) . ?
C2 N3 1.365(7) . ?
C2 H2B 0.9300 . ?
N3 N4 1.401(6) . ?
C3 N4 1.264(8) . ?
C3 C4 1.465(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.394(8) . ?
C4 C9 1.401(8) . ?
C5 C6 1.392(9) . ?
C5 H5A 0.9300 . ?
C6 C7 1.376(8) . ?
C6 H6A 0.9300 . ?
C7 C8 1.379(8) . ?
C8 C9 1.385(8) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 112.2(5) . . ?
C1 N1 H1A 123.9 . . ?
N2 N1 H1A 123.9 . . ?
N1 C1 N3 106.8(5) . . ?
N1 C1 H1B 126.6 . . ?
N3 C1 H1B 126.6 . . ?
C2 N2 N1 103.4(5) . . ?
N2 C2 N3 111.2(5) . . ?
N2 C2 H2B 124.4 . . ?
N3 C2 H2B 124.4 . . ?
C1 N3 C2 106.4(5) . . ?
C1 N3 N4 132.2(5) . . ?
C2 N3 N4 121.3(5) . . ?
N4 C3 C4 121.0(5) . . ?
N4 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C3 N4 N3 116.2(5) . . ?
C5 C4 C9 119.7(6) . . ?
C5 C4 C3 121.7(5) . . ?
C9 C4 C3 118.6(5) . . ?
C6 C5 C4 119.7(6) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C7 C6 C5 119.8(6) . . ?
C7 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
C6 C7 C8 121.2(5) . . ?
C6 C7 I 119.1(4) . . ?
C8 C7 I 119.6(4) . . ?
C7 C8 C9 119.7(5) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
C8 C9 C4 119.9(5) . . ?
C8 C9 H9A 120.1 . . ?
C4 C9 H9A 120.1 . . ?

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
N2 N1 C1 N3 -1.6(7) . . . . ?
C1 N1 N2 C2 1.3(7) . . . . ?
N1 N2 C2 N3 -0.6(7) . . . . ?
N1 C1 N3 C2 1.1(7) . . . . ?
N1 C1 N3 N4 176.0(5) . . . . ?
N2 C2 N3 C1 -0.3(7) . . . . ?
N2 C2 N3 N4 -175.9(5) . . . . ?
C4 C3 N4 N3 -177.1(5) . . . . ?
C1 N3 N4 C3 17.8(9) . . . . ?
C2 N3 N4 C3 -168.0(6) . . . . ?
N4 C3 C4 C5 3.2(9) . . . . ?
N4 C3 C4 C9 -178.8(6) . . . . ?
C9 C4 C5 C6 1.3(9) . . . . ?
C3 C4 C5 C6 179.3(6) . . . . ?
C4 C5 C6 C7 -0.9(9) . . . . ?
C5 C6 C7 C8 1.1(9) . . . . ?
C5 C6 C7 I -178.0(4) . . . . ?
C6 C7 C8 C9 -1.7(9) . . . . ?
I C7 C8 C9 177.4(4) . . . . ?
C7 C8 C9 C4 2.1(9) . . . . ?
C5 C4 C9 C8 -1.9(9) . . . . ?
C3 C4 C9 C8 -180.0(5) . . . . ?

_refine_diff_density_max         0.565
_refine_diff_density_min         -0.891
_refine_diff_density_rms         0.131

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_X_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1519856'
_audit_update_record             
;
2017-06-29 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H7 Br N4'
_chemical_formula_weight         251.10

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   4.2810(9)
_cell_length_b                   11.572(2)
_cell_length_c                   19.146(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.49(3)
_cell_angle_gamma                90
_cell_volume                     946.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.304
_shelx_estimated_absorpt_T_min   0.480
_shelx_estimated_absorpt_T_max   0.673
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.057
_diffrn_reflns_theta_max         25.362
_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             1733
_reflns_number_gt                953
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0350P)²] 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         1733
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
Br Br 0.16378(17) 0.62763(6) 0.59002(4) 0.0595(3) Uani 1 1 d . . . . .
N1 N 1.4045(14) 1.0295(6) 0.2179(3) 0.0698(18) Uani 1 1 d . . . . .
C1 C 1.2567(16) 0.9529(7) 0.2527(3) 0.060(2) Uani 1 1 d . . . . .
H1B H 1.2480 0.8744 0.2421 0.072 Uiso 1 1 calc R U . . .
N2 N 1.3637(13) 1.1356(6) 0.2498(3) 0.0660(16) Uani 1 1 d . . . . .
C2 C 1.1957(16) 1.1159(6) 0.3028(3) 0.0620(19) Uani 1 1 d . . . . .
H2B H 1.1379 1.1724 0.3341 0.074 Uiso 1 1 calc R U . . .
C3 C 0.8748(14) 0.8545(6) 0.3591(3) 0.0483(17) Uani 1 1 d . . . . .
H3A H 0.9427 0.8084 0.3232 0.058 Uiso 1 1 calc R U . . .
N3 N 1.1153(11) 1.0033(4) 0.3070(3) 0.0463(14) Uani 1 1 d . . . . .
N4 N 0.9424(12) 0.9614(4) 0.3606(2) 0.0487(14) Uani 1 1 d . . . . .
C4 C 0.6922(14) 0.8033(5) 0.4128(3) 0.0445(16) Uani 1 1 d . . . . .
C5 C 0.6354(13) 0.8639(5) 0.4740(3) 0.0479(16) Uani 1 1 d . . . . .
H5A H 0.7115 0.9387 0.4803 0.057 Uiso 1 1 calc R U . . .
C6 C 0.4696(14) 0.8143(6) 0.5244(3) 0.0494(17) Uani 1 1 d . . . . .
H6A H 0.4276 0.8561 0.5643 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3624(15) 0.7013(5) 0.5167(3) 0.0472(17) Uani 1 1 d . . . . .
C8 C 0.4176(14) 0.6401(6) 0.4564(3) 0.0532(17) Uani 1 1 d . . . . .
H8A H 0.3442 0.5649 0.4507 0.064 Uiso 1 1 calc R U . . .
C9 C 0.5817(15) 0.6916(6) 0.4053(3) 0.0529(18) Uani 1 1 d . . . . .
H9A H 0.6190 0.6504 0.3650 0.063 Uiso 1 1 calc R U . . .


_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
Br C7 1.889(6) . ?
N1 C1 1.296(8) . ?
N1 N2 1.387(8) . ?
C1 N3 1.365(7) . ?
C1 H1B 0.9300 . ?
N2 C2 1.299(8) . ?
C2 N3 1.351(7) . ?
C2 H2B 0.9300 . ?
C3 N4 1.270(7) . ?
C3 C4 1.455(8) . ?
C3 H3A 0.9300 . ?
N3 N4 1.389(6) . ?
C4 C9 1.381(8) . ?
C4 C5 1.400(8) . ?
C5 C6 1.359(8) . ?
C5 H5A 0.9300 . ?
C6 C7 1.390(8) . ?
C6 H6A 0.9300 . ?
C7 C8 1.385(8) . ?
C8 C9 1.375(8) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 107.5(6) . . ?
N1 C1 N3 110.6(6) . . ?
N1 C1 H1B 124.7 . . ?
N3 C1 H1B 124.7 . . ?
C2 N2 N1 106.2(6) . . ?
N2 C2 N3 111.8(7) . . ?
N2 C2 H2B 124.1 . . ?
N3 C2 H2B 124.1 . . ?
N4 C3 C4 120.8(5) . . ?
N4 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C2 N3 C1 103.9(5) . . ?
C2 N3 N4 122.0(5) . . ?
C1 N3 N4 133.9(6) . . ?
C3 N4 N3 117.1(5) . . ?
C9 C4 C5 118.7(6) . . ?
C9 C4 C3 120.2(6) . . ?
C5 C4 C3 121.1(6) . . ?
C6 C5 C4 120.5(6) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C7 120.3(6) . . ?
C5 C6 H6A 119.8 . . ?
C7 C6 H6A 119.8 . . ?
C8 C7 C6 119.8(6) . . ?
C8 C7 Br 119.7(5) . . ?
C6 C7 Br 120.4(5) . . ?
C9 C8 C7 119.4(6) . . ?
C9 C8 H8A 120.3 . . ?
C7 C8 H8A 120.3 . . ?
C8 C9 C4 121.2(6) . . ?
C8 C9 H9A 119.4 . . ?
C4 C9 H9A 119.4 . . ?

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
N2 N1 C1 N3 0.3(8) . . . . ?
C1 N1 N2 C2 0.8(8) . . . . ?
N1 N2 C2 N3 -1.7(8) . . . . ?
N2 C2 N3 C1 1.8(8) . . . . ?
N2 C2 N3 N4 178.3(5) . . . . ?
N1 C1 N3 C2 -1.2(8) . . . . ?
N1 C1 N3 N4 -177.1(6) . . . . ?
C4 C3 N4 N3 -179.5(5) . . . . ?
C2 N3 N4 C3 178.9(6) . . . . ?
C1 N3 N4 C3 -5.8(10) . . . . ?
N4 C3 C4 C9 170.6(6) . . . . ?
N4 C3 C4 C5 -11.9(10) . . . . ?
C9 C4 C5 C6 -1.2(9) . . . . ?
C3 C4 C5 C6 -178.7(6) . . . . ?
C4 C5 C6 C7 1.9(10) . . . . ?
C5 C6 C7 C8 -1.7(10) . . . . ?
C5 C6 C7 Br 174.5(5) . . . . ?
C6 C7 C8 C9 0.8(10) . . . . ?
Br C7 C8 C9 -175.4(5) . . . . ?
C7 C8 C9 C4 -0.1(10) . . . . ?
C5 C4 C9 C8 0.3(10) . . . . ?
C3 C4 C9 C8 177.8(6) . . . . ?

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.098

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_X_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1519857'
_audit_update_record             
;
2017-06-29 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H7 I N4'
_chemical_formula_weight         298.09

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'
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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   4.4720(9)
_cell_length_b                   11.701(2)
_cell_length_c                   19.032(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.38(3)
_cell_angle_gamma                90
_cell_volume                     991.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.997
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.194
_shelx_estimated_absorpt_T_min   0.568
_shelx_estimated_absorpt_T_max   0.741
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.046
_diffrn_reflns_theta_max         25.362
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1811
_reflns_number_gt                1191
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0520P)²] 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         1811
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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_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
I I 0.16287(11) 0.37267(4) 1.09294(3) 0.0517(2) Uani 1 1 d . . . . .
N1 N 1.4131(18) -0.0153(7) 0.7191(4) 0.068(2) Uani 1 1 d . . . . .
C1 C 1.2640(18) 0.0553(8) 0.7558(4) 0.059(2) Uani 1 1 d . . . . .
H1B H 1.2503 0.1335 0.7471 0.071 Uiso 1 1 calc R U . . .
N2 N 1.3826(17) -0.1216(6) 0.7484(4) 0.0692(19) Uani 1 1 d . . . . .
C2 C 1.217(2) -0.1072(7) 0.8025(5) 0.065(2) Uani 1 1 d . . . . .
H2B H 1.1658 -0.1651 0.8326 0.078 Uiso 1 1 calc R U . . .
C3 C 0.8763(16) 0.1456(6) 0.8576(4) 0.0455(18) Uani 1 1 d . . . . .
H3A H 0.9303 0.1920 0.8212 0.055 Uiso 1 1 calc R U . . .
N3 N 1.1332(14) 0.0029(5) 0.8073(3) 0.0472(15) Uani 1 1 d . . . . .
N4 N 0.9581(14) 0.0395(5) 0.8597(3) 0.0474(15) Uani 1 1 d . . . . .
C4 C 0.7021(17) 0.1932(6) 0.9108(4) 0.0432(17) Uani 1 1 d . . . . .
C5 C 0.6423(17) 0.1327(6) 0.9705(4) 0.0486(17) Uani 1 1 d . . . . .
H5A H 0.7136 0.0583 0.9763 0.058 Uiso 1 1 calc R U . . .
C6 C 0.4791(18) 0.1797(6) 1.0219(4) 0.052(2) Uani 1 1 d . . . . .
H6A H 0.4438 0.1383 1.0620 0.063 Uiso 1 1 calc R U . . .
C7 C 0.3686(16) 0.2913(6) 1.0117(4) 0.0418(17) Uani 1 1 d . . . . .
C8 C 0.4204(16) 0.3512(6) 0.9527(4) 0.0449(18) Uani 1 1 d . . . . .
H8A H 0.3436 0.4247 0.9462 0.054 Uiso 1 1 calc R U . . .
C9 C 0.5896(17) 0.3025(6) 0.9016(4) 0.0495(19) Uani 1 1 d . . . . .
H9A H 0.6256 0.3441 0.8616 0.059 Uiso 1 1 calc R U . . .


_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
I C7 2.100(7) . ?
N1 C1 1.305(10) . ?
N1 N2 1.374(9) . ?
C1 N3 1.336(10) . ?
C1 H1B 0.9300 . ?
N2 C2 1.335(11) . ?
C2 N3 1.347(9) . ?
C2 H2B 0.9300 . ?
C3 N4 1.294(9) . ?
C3 C4 1.447(10) . ?
C3 H3A 0.9300 . ?
N3 N4 1.391(8) . ?
C4 C9 1.380(10) . ?
C4 C5 1.386(10) . ?
C5 C6 1.388(11) . ?
C5 H5A 0.9300 . ?
C6 C7 1.403(10) . ?
C6 H6A 0.9300 . ?
C7 C8 1.362(9) . ?
C8 C9 1.407(10) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 106.3(7) . . ?
N1 C1 N3 112.5(8) . . ?
N1 C1 H1B 123.7 . . ?
N3 C1 H1B 123.7 . . ?
C2 N2 N1 106.4(7) . . ?
N2 C2 N3 110.5(8) . . ?
N2 C2 H2B 124.7 . . ?
N3 C2 H2B 124.7 . . ?
N4 C3 C4 121.2(7) . . ?
N4 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C1 N3 C2 104.2(7) . . ?
C1 N3 N4 134.3(6) . . ?
C2 N3 N4 121.4(6) . . ?
C3 N4 N3 116.7(6) . . ?
C9 C4 C5 118.8(7) . . ?
C9 C4 C3 118.8(7) . . ?
C5 C4 C3 122.4(7) . . ?
C4 C5 C6 122.0(7) . . ?
C4 C5 H5A 119.0 . . ?
C6 C5 H5A 119.0 . . ?
C5 C6 C7 118.2(7) . . ?
C5 C6 H6A 120.9 . . ?
C7 C6 H6A 120.9 . . ?
C8 C7 C6 120.6(7) . . ?
C8 C7 I 119.5(5) . . ?
C6 C7 I 119.5(5) . . ?
C7 C8 C9 120.3(6) . . ?
C7 C8 H8A 119.8 . . ?
C9 C8 H8A 119.8 . . ?
C4 C9 C8 120.1(7) . . ?
C4 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?

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
N2 N1 C1 N3 -0.6(10) . . . . ?
C1 N1 N2 C2 -0.8(10) . . . . ?
N1 N2 C2 N3 1.9(11) . . . . ?
N1 C1 N3 C2 1.8(10) . . . . ?
N1 C1 N3 N4 179.1(8) . . . . ?
N2 C2 N3 C1 -2.2(10) . . . . ?
N2 C2 N3 N4 179.9(7) . . . . ?
C4 C3 N4 N3 -178.0(6) . . . . ?
C1 N3 N4 C3 6.6(13) . . . . ?
C2 N3 N4 C3 -176.4(8) . . . . ?
N4 C3 C4 C9 -172.2(7) . . . . ?
N4 C3 C4 C5 7.3(11) . . . . ?
C9 C4 C5 C6 -1.6(11) . . . . ?
C3 C4 C5 C6 179.0(7) . . . . ?
C4 C5 C6 C7 1.1(12) . . . . ?
C5 C6 C7 C8 0.2(11) . . . . ?
C5 C6 C7 I -173.2(6) . . . . ?
C6 C7 C8 C9 -0.9(11) . . . . ?
I C7 C8 C9 172.4(6) . . . . ?
C5 C4 C9 C8 0.7(11) . . . . ?
C3 C4 C9 C8 -179.7(7) . . . . ?
C7 C8 C9 C4 0.5(11) . . . . ?

_refine_diff_density_max         0.665
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.128

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_wjw
_database_code_depnum_ccdc_archive 'CCDC 1519859'
_audit_update_record             
;
2017-06-29 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 Br2 Cl N8 O4'
_chemical_formula_weight         602.65

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'
Br Br -0.2901 2.4595 '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'
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'

_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                   8.0000(16)
_cell_length_b                   9.886(2)
_cell_length_c                   14.320(3)
_cell_angle_alpha                95.05(3)
_cell_angle_beta                 97.80(3)
_cell_angle_gamma                105.59(3)
_cell_volume                     1071.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.868
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.953
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.1008
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.448
_diffrn_reflns_theta_max         26.097
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             3893
_reflns_number_gt                2061
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (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)+(0.1242P)²+0.3842P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3893
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1625
_refine_ls_R_factor_gt           0.0896
_refine_ls_wR_factor_ref         0.2495
_refine_ls_wR_factor_gt          0.2170
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.004

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
Br1 Br 0.11276(15) 0.32918(13) -0.09718(10) 0.0663(5) Uani 1 1 d . . . . .
N1 N 0.6343(10) 0.9760(8) 0.1326(6) 0.044(2) Uani 1 1 d . . . . .
N2 N 0.7510(11) 1.1063(8) 0.1540(6) 0.046(2) Uani 1 1 d . . . . .
N3 N 0.9577(12) 1.3048(9) 0.1580(8) 0.059(3) Uani 1 1 d . . . . .
N4 N 0.8759(12) 1.3080(10) 0.2340(6) 0.055(2) Uani 1 1 d . . . . .
H4 H 0.9015 1.3789 0.2780 0.066 Uiso 1 1 d R U . . .
C1 C 0.2726(15) 0.5078(12) -0.0472(8) 0.055(3) Uani 1 1 d . . . . .
C2 C 0.3836(14) 0.5627(11) -0.1006(7) 0.050(3) Uani 1 1 d . . . . .
H2 H 0.3838 0.5150 -0.1595 0.060 Uiso 1 1 calc R U . . .
C3 C 0.5063(15) 0.6987(13) -0.0670(8) 0.057(3) Uani 1 1 d . . . . .
H3 H 0.5878 0.7405 -0.1040 0.069 Uiso 1 1 calc R U . . .
C4 C 0.5029(12) 0.7678(10) 0.0214(7) 0.044(2) Uani 1 1 d . . . . .
C5 C 0.3779(15) 0.7023(12) 0.0748(8) 0.057(3) Uani 1 1 d . . . . .
H5 H 0.3718 0.7462 0.1339 0.069 Uiso 1 1 calc R U . . .
C6 C 0.2671(14) 0.5751(12) 0.0392(8) 0.055(3) Uani 1 1 d . . . . .
H6 H 0.1836 0.5313 0.0746 0.066 Uiso 1 1 calc R U . . .
C7 C 0.6300(14) 0.9115(12) 0.0548(9) 0.059(3) Uani 1 1 d . . . . .
H7 H 0.7074 0.9525 0.0155 0.070 Uiso 1 1 calc R U . . .
C8 C 0.8739(12) 1.1750(9) 0.1128(8) 0.050(3) Uani 1 1 d . . . . .
H8 H 0.9020 1.1382 0.0569 0.060 Uiso 1 1 calc R U . . .
C9 C 0.7574(14) 1.1936(10) 0.2325(8) 0.049(3) Uani 1 1 d . . . . .
H9 H 0.6859 1.1731 0.2784 0.059 Uiso 1 1 calc R U . . .
Br2 Br 0.36580(17) 0.47976(14) 0.30461(9) 0.0739(5) Uani 1 1 d . . . . .
N5 N 0.8989(11) 1.1499(8) 0.4800(6) 0.048(2) Uani 1 1 d . . . . .
N6 N 0.9831(10) 1.2719(8) 0.5369(6) 0.047(2) Uani 1 1 d . . . . .
N7 N 1.1714(10) 1.4857(9) 0.5690(7) 0.058(3) Uani 1 1 d . . . . .
N8 N 1.0692(11) 1.4568(8) 0.6402(7) 0.052(2) Uani 1 1 d . . . . .
C10 C 0.4985(14) 0.6584(11) 0.3684(8) 0.049(3) Uani 1 1 d . . . . .
C11 C 0.6172(13) 0.7487(11) 0.3240(8) 0.050(3) Uani 1 1 d . . . . .
H11 H 0.6309 0.7233 0.2620 0.060 Uiso 1 1 calc R U . . .
C12 C 0.7115(14) 0.8736(11) 0.3727(7) 0.047(2) Uani 1 1 d . . . . .
H12 H 0.7910 0.9341 0.3426 0.057 Uiso 1 1 calc R U . . .
C13 C 0.6990(15) 0.9188(13) 0.4647(8) 0.055(3) Uani 1 1 d . . . . .
C14 C 0.5812(14) 0.8311(11) 0.5079(7) 0.051(3) Uani 1 1 d . . . . .
H14 H 0.5676 0.8588 0.5695 0.061 Uiso 1 1 calc R U . . .
C15 C 0.4808(14) 0.6997(12) 0.4604(8) 0.055(3) Uani 1 1 d . . . . .
H15 H 0.4012 0.6393 0.4906 0.066 Uiso 1 1 calc R U . . .
C16 C 0.7908(13) 1.0543(10) 0.5174(8) 0.049(3) Uani 1 1 d . . . . .
H16 H 0.7731 1.0746 0.5793 0.059 Uiso 1 1 calc R U . . .
C17 C 1.1043(11) 1.3654(8) 0.5081(8) 0.044(3) Uani 1 1 d . . . . .
H17 H 1.1421 1.3510 0.4504 0.052 Uiso 1 1 calc R U . . .
C18 C 0.9664(15) 1.3396(11) 0.6214(8) 0.052(3) Uani 1 1 d . . . . .
H18 H 0.8858 1.3002 0.6596 0.063 Uiso 1 1 calc R U . . .
Cl3 Cl 0.2016(4) 0.0117(3) 0.22015(19) 0.0520(7) Uani 1 1 d . . . . .
O1 O 0.2487(13) -0.1096(9) 0.2508(7) 0.079(3) Uani 1 1 d . . . . .
O2 O 0.0679(13) 0.0307(13) 0.2658(7) 0.103(4) Uani 1 1 d . . . . .
O3 O 0.3404(11) 0.1290(9) 0.2415(7) 0.087(3) Uani 1 1 d . . . . .
O4 O 0.1506(12) -0.0110(10) 0.1202(6) 0.083(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
Br1 C1 1.893(12) . ?
N1 C7 1.226(14) . ?
N1 N2 1.353(10) . ?
N2 C8 1.283(11) . ?
N2 C9 1.342(13) . ?
N3 C8 1.337(12) . ?
N3 N4 1.347(12) . ?
N4 C9 1.261(12) . ?
N4 H4 0.8600 . ?
C1 C2 1.291(14) . ?
C1 C6 1.364(15) . ?
C2 C3 1.432(14) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(14) . ?
C4 C7 1.500(14) . ?
C5 C6 1.338(15) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
Br2 C10 1.877(10) . ?
N5 C16 1.306(12) . ?
N5 N6 1.347(11) . ?
N6 C17 1.287(11) . ?
N6 C18 1.371(13) . ?
N7 C17 1.346(13) . ?
N7 N8 1.393(12) . ?
N8 C18 1.210(12) . ?
C10 C11 1.382(14) . ?
C10 C15 1.382(15) . ?
C11 C12 1.336(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(15) . ?
C12 H12 0.9300 . ?
C13 C14 1.355(14) . ?
C13 C16 1.429(15) . ?
C14 C15 1.389(14) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
Cl3 O3 1.351(7) . ?
Cl3 O2 1.372(9) . ?
Cl3 O4 1.414(9) . ?
Cl3 O1 1.436(9) . ?

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
C7 N1 N2 116.4(9) . . ?
C8 N2 C9 104.5(9) . . ?
C8 N2 N1 133.0(9) . . ?
C9 N2 N1 122.4(8) . . ?
C8 N3 N4 101.5(8) . . ?
C9 N4 N3 111.3(9) . . ?
C9 N4 H4 124.5 . . ?
N3 N4 H4 124.3 . . ?
C2 C1 C6 122.4(11) . . ?
C2 C1 Br1 115.9(9) . . ?
C6 C1 Br1 121.6(9) . . ?
C1 C2 C3 118.5(10) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.6(10) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 118.6(10) . . ?
C5 C4 C7 122.4(10) . . ?
C3 C4 C7 119.0(9) . . ?
C6 C5 C4 118.7(10) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 122.1(11) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
N1 C7 C4 121.6(9) . . ?
N1 C7 H7 119.2 . . ?
C4 C7 H7 119.2 . . ?
N2 C8 N3 113.5(10) . . ?
N2 C8 H8 123.3 . . ?
N3 C8 H8 123.3 . . ?
N4 C9 N2 109.2(9) . . ?
N4 C9 H9 125.4 . . ?
N2 C9 H9 125.4 . . ?
C16 N5 N6 116.3(9) . . ?
C17 N6 N5 119.7(9) . . ?
C17 N6 C18 102.8(9) . . ?
N5 N6 C18 137.1(8) . . ?
C17 N7 N8 100.8(7) . . ?
C18 N8 N7 110.6(9) . . ?
C11 C10 C15 119.5(10) . . ?
C11 C10 Br2 120.1(8) . . ?
C15 C10 Br2 120.5(8) . . ?
C12 C11 C10 118.0(10) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C11 C12 C13 124.5(11) . . ?
C11 C12 H12 117.8 . . ?
C13 C12 H12 117.8 . . ?
C14 C13 C12 117.5(11) . . ?
C14 C13 C16 116.3(10) . . ?
C12 C13 C16 126.1(11) . . ?
C13 C14 C15 120.2(10) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.3(10) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N5 C16 C13 121.1(10) . . ?
N5 C16 H16 119.4 . . ?
C13 C16 H16 119.4 . . ?
N6 C17 N7 114.0(10) . . ?
N6 C17 H17 123.0 . . ?
N7 C17 H17 123.0 . . ?
N8 C18 N6 111.7(9) . . ?
N8 C18 H18 124.1 . . ?
N6 C18 H18 124.1 . . ?
O3 Cl3 O2 109.5(7) . . ?
O3 Cl3 O4 107.4(6) . . ?
O2 Cl3 O4 111.8(6) . . ?
O3 Cl3 O1 110.9(6) . . ?
O2 Cl3 O1 108.1(6) . . ?
O4 Cl3 O1 109.1(6) . . ?

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
C7 N1 N2 C8 -7.6(17) . . . . ?
C7 N1 N2 C9 173.3(11) . . . . ?
C8 N3 N4 C9 -0.5(12) . . . . ?
C6 C1 C2 C3 0.7(17) . . . . ?
Br1 C1 C2 C3 179.2(8) . . . . ?
C1 C2 C3 C4 -0.1(16) . . . . ?
C2 C3 C4 C5 -0.5(16) . . . . ?
C2 C3 C4 C7 -178.8(10) . . . . ?
C3 C4 C5 C6 0.5(16) . . . . ?
C7 C4 C5 C6 178.8(10) . . . . ?
C4 C5 C6 C1 0.1(18) . . . . ?
C2 C1 C6 C5 -0.7(19) . . . . ?
Br1 C1 C6 C5 -179.1(9) . . . . ?
N2 N1 C7 C4 -178.2(9) . . . . ?
C5 C4 C7 N1 2.8(17) . . . . ?
C3 C4 C7 N1 -178.9(11) . . . . ?
C9 N2 C8 N3 -2.0(13) . . . . ?
N1 N2 C8 N3 178.8(10) . . . . ?
N4 N3 C8 N2 1.6(12) . . . . ?
N3 N4 C9 N2 -0.7(13) . . . . ?
C8 N2 C9 N4 1.6(12) . . . . ?
N1 N2 C9 N4 -179.1(9) . . . . ?
C16 N5 N6 C17 173.2(9) . . . . ?
C16 N5 N6 C18 -15.2(18) . . . . ?
C17 N7 N8 C18 0.9(12) . . . . ?
C15 C10 C11 C12 0.3(16) . . . . ?
Br2 C10 C11 C12 -178.6(8) . . . . ?
C10 C11 C12 C13 0.1(17) . . . . ?
C11 C12 C13 C14 -0.9(17) . . . . ?
C11 C12 C13 C16 -176.5(11) . . . . ?
C12 C13 C14 C15 1.2(17) . . . . ?
C16 C13 C14 C15 177.3(10) . . . . ?
C11 C10 C15 C14 0.0(17) . . . . ?
Br2 C10 C15 C14 179.0(9) . . . . ?
C13 C14 C15 C10 -0.8(18) . . . . ?
N6 N5 C16 C13 -177.8(9) . . . . ?
C14 C13 C16 N5 -175.7(10) . . . . ?
C12 C13 C16 N5 0.0(17) . . . . ?
N5 N6 C17 N7 176.5(9) . . . . ?
C18 N6 C17 N7 2.3(12) . . . . ?
N8 N7 C17 N6 -2.1(11) . . . . ?
N7 N8 C18 N6 0.4(14) . . . . ?
C17 N6 C18 N8 -1.6(13) . . . . ?
N5 N6 C18 N8 -174.1(11) . . . . ?

_refine_diff_density_max         1.148
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.137

_shelxl_version_number           2014-3

