# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2173224'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University of Rennes 
France
;
_audit_update_record             
;
2022-05-17 deposited with the CCDC.	2022-08-24 downloaded from the CCDC.
;

_audit_creation_date             2019-02-12T11:07:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C8 H7 Cl N2'
_chemical_formula_moiety         'C8 H7 Cl N2'
_chemical_formula_weight         166.61

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0888(5)
_cell_length_b                   12.0248(7)
_cell_length_c                   8.8930(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.940(3)
_cell_angle_gamma                90
_cell_volume                     807.86(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2977
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.41
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.37
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.972

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.6628  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------# 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.004067
_diffrn_orient_matrix_ub_12      0.021882
_diffrn_orient_matrix_ub_13      0.109753
_diffrn_orient_matrix_ub_21      -0.128354
_diffrn_orient_matrix_ub_22      -0.018814
_diffrn_orient_matrix_ub_23      -0.031308
_diffrn_orient_matrix_ub_31      0.032103
_diffrn_orient_matrix_ub_32      -0.077994
_diffrn_orient_matrix_ub_33      0.038345
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_number            6626
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.696
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             1853
_reflns_number_gt                1427
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.2209P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1853
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.1912(2) -0.10091(15) 0.9800(2) 0.0424(4) Uani 1 1 d . . . . .
C2 C 0.1491(3) -0.21077(15) 1.0012(2) 0.0462(4) Uani 1 1 d . . . . .
C3 C 0.2604(3) -0.27096(19) 1.1315(3) 0.0630(6) Uani 1 1 d . . . . .
H3 H 0.2361 -0.3447 1.1478 0.076 Uiso 1 1 calc R U . . .
C4 C 0.4069(3) -0.2182(2) 1.2352(3) 0.0774(7) Uani 1 1 d . . . . .
H4 H 0.4822 -0.2569 1.3237 0.093 Uiso 1 1 calc R U . . .
C5 C 0.4463(3) -0.1089(3) 1.2119(3) 0.0755(7) Uani 1 1 d . . . . .
H5 H 0.5476 -0.0763 1.2847 0.091 Uiso 1 1 calc R U . . .
C6 C 0.3393(3) -0.04739(18) 1.0838(2) 0.0591(5) Uani 1 1 d . . . . .
H6 H 0.3651 0.0261 1.0679 0.071 Uiso 1 1 calc R U . . .
C7 C -0.0589(2) -0.15449(15) 0.7863(2) 0.0454(4) Uani 1 1 d . . . . .
C8 C -0.2160(3) -0.14778(19) 0.6357(2) 0.0636(6) Uani 1 1 d . . . . .
H8A H -0.1784 -0.1463 0.5449 0.095 Uiso 1 1 calc R U . . .
H8B H -0.2813 -0.0813 0.6367 0.095 Uiso 1 1 calc R U . . .
H8C H -0.2902 -0.2114 0.628 0.095 Uiso 1 1 calc R U . . .
N1 N 0.0555(2) -0.06702(11) 0.84222(18) 0.0440(3) Uani 1 1 d . . . . .
N2 N -0.0075(2) -0.24165(12) 0.87987(19) 0.0509(4) Uani 1 1 d . . . . .
Cl1 Cl 0.04317(6) 0.05847(3) 0.75290(6) 0.05082(18) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.382(2) . ?
C1 C6 1.383(3) . ?
C1 C2 1.394(2) . ?
C2 N2 1.389(2) . ?
C2 C3 1.390(3) . ?
C3 C4 1.370(4) . ?
C3 H3 0.93 . ?
C4 C5 1.385(4) . ?
C4 H4 0.93 . ?
C5 C6 1.374(3) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 N2 1.310(2) . ?
C7 N1 1.372(2) . ?
C7 C8 1.483(3) . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
N1 Cl1 1.6916(14) . ?

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 C1 C6 132.74(18) . . ?
N1 C1 C2 104.14(15) . . ?
C6 C1 C2 123.11(18) . . ?
N2 C2 C3 130.36(18) . . ?
N2 C2 C1 110.32(16) . . ?
C3 C2 C1 119.32(19) . . ?
C4 C3 C2 117.8(2) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 H4 119 . . ?
C5 C4 H4 119 . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 116.2(2) . . ?
C5 C6 H6 121.9 . . ?
C1 C6 H6 121.9 . . ?
N2 C7 N1 111.29(16) . . ?
N2 C7 C8 126.31(17) . . ?
N1 C7 C8 122.38(17) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 N1 C1 108.33(14) . . ?
C7 N1 Cl1 126.49(13) . . ?
C1 N1 Cl1 125.05(12) . . ?
C7 N2 C2 105.90(15) . . ?

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
N1 C1 C2 N2 -0.14(18) . . . . ?
C6 C1 C2 N2 179.34(16) . . . . ?
N1 C1 C2 C3 -179.99(16) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
N2 C2 C3 C4 -179.1(2) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
N1 C1 C6 C5 179.51(19) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
N2 C7 N1 C1 0.9(2) . . . . ?
C8 C7 N1 C1 -177.47(17) . . . . ?
N2 C7 N1 Cl1 177.00(12) . . . . ?
C8 C7 N1 Cl1 -1.4(3) . . . . ?
C6 C1 N1 C7 -179.85(19) . . . . ?
C2 C1 N1 C7 -0.44(18) . . . . ?
C6 C1 N1 Cl1 4.0(3) . . . . ?
C2 C1 N1 Cl1 -176.58(12) . . . . ?
N1 C7 N2 C2 -1.0(2) . . . . ?
C8 C7 N2 C2 177.34(18) . . . . ?
C3 C2 N2 C7 -179.48(19) . . . . ?
C1 C2 N2 C7 0.70(19) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2173226'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University of Rennes 
France
;
_audit_update_record             
;
2022-05-17 deposited with the CCDC.	2022-08-24 downloaded from the CCDC.
;

_audit_creation_date             2022-05-16T10:48:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C7 H4 Cl2 N2'
_chemical_formula_moiety         'C7 H4 Cl2 N2'
_chemical_formula_weight         187.02

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   7.9412(15)
_cell_length_b                   9.2207(16)
_cell_length_c                   10.7738(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.837(9)
_cell_angle_gamma                90
_cell_volume                     779.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1290
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      23.8
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.977

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.6837  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.109692
_diffrn_orient_matrix_ub_12      -0.011154
_diffrn_orient_matrix_ub_13      0.058693
_diffrn_orient_matrix_ub_21      -0.060614
_diffrn_orient_matrix_ub_22      -0.055456
_diffrn_orient_matrix_ub_23      0.059571
_diffrn_orient_matrix_ub_31      0.023105
_diffrn_orient_matrix_ub_32      -0.092531
_diffrn_orient_matrix_ub_33      -0.042777
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.043
_diffrn_reflns_number            4738
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.923
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.98
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.98
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.98
_reflns_Friedel_coverage         0
_reflns_number_total             1745
_reflns_number_gt                1147
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+0.3414P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1745
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.079
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.4621(3) 0.0070(3) 0.7045(2) 0.0429(6) Uani 1 1 d . . . . .
C2 C 0.4747(4) -0.1283(3) 0.7617(3) 0.0549(7) Uani 1 1 d . . . . .
H2 H 0.5524 -0.1448 0.8341 0.066 Uiso 1 1 calc R U . . .
C3 C 0.3698(4) -0.2367(3) 0.7089(3) 0.0627(8) Uani 1 1 d . . . . .
H3 H 0.3763 -0.3277 0.7464 0.075 Uiso 1 1 calc R U . . .
C4 C 0.2534(4) -0.2136(3) 0.6000(3) 0.0640(9) Uani 1 1 d . . . . .
H4 H 0.1846 -0.29 0.5664 0.077 Uiso 1 1 calc R U . . .
C5 C 0.2377(4) -0.0806(3) 0.5410(3) 0.0554(8) Uani 1 1 d . . . . .
H5 H 0.16 -0.0645 0.4684 0.066 Uiso 1 1 calc R U . . .
C6 C 0.3441(3) 0.0269(3) 0.5960(2) 0.0413(6) Uani 1 1 d . . . . .
C7 C 0.4869(3) 0.2277(3) 0.6546(2) 0.0443(6) Uani 1 1 d . . . . .
N1 N 0.5503(3) 0.1339(2) 0.73843(19) 0.0476(6) Uani 1 1 d . . . . .
N2 N 0.3631(3) 0.1711(2) 0.56586(17) 0.0435(5) Uani 1 1 d . . . . .
Cl1 Cl 0.24518(8) 0.25870(8) 0.44486(5) 0.0512(2) Uani 1 1 d . . . . .
Cl2 Cl 0.54339(11) 0.40350(8) 0.64964(7) 0.0662(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.384(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.393(3) . ?
C2 C3 1.368(4) . ?
C2 H2 0.93 . ?
C3 C4 1.393(4) . ?
C3 H3 0.93 . ?
C4 C5 1.379(4) . ?
C4 H4 0.93 . ?
C5 C6 1.377(4) . ?
C5 H5 0.93 . ?
C6 N2 1.383(3) . ?
C7 N1 1.295(3) . ?
C7 N2 1.365(3) . ?
C7 Cl2 1.685(3) . ?
N2 Cl1 1.689(2) . ?

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 C1 C2 130.1(2) . . ?
N1 C1 C6 111.0(2) . . ?
C2 C1 C6 119.0(3) . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C6 C5 C4 115.8(3) . . ?
C6 C5 H5 122.1 . . ?
C4 C5 H5 122.1 . . ?
C5 C6 N2 132.3(2) . . ?
C5 C6 C1 123.8(3) . . ?
N2 C6 C1 103.9(2) . . ?
N1 C7 N2 113.2(2) . . ?
N1 C7 Cl2 126.0(2) . . ?
N2 C7 Cl2 120.8(2) . . ?
C7 N1 C1 104.7(2) . . ?
C7 N2 C6 107.2(2) . . ?
C7 N2 Cl1 127.72(19) . . ?
C6 N2 Cl1 125.00(17) . . ?

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
N1 C1 C2 C3 179.3(3) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 N2 -178.9(3) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
N1 C1 C6 C5 -179.6(2) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
N1 C1 C6 N2 -0.4(3) . . . . ?
C2 C1 C6 N2 179.1(2) . . . . ?
N2 C7 N1 C1 -0.7(3) . . . . ?
Cl2 C7 N1 C1 178.9(2) . . . . ?
C2 C1 N1 C7 -178.8(3) . . . . ?
C6 C1 N1 C7 0.6(3) . . . . ?
N1 C7 N2 C6 0.4(3) . . . . ?
Cl2 C7 N2 C6 -179.11(18) . . . . ?
N1 C7 N2 Cl1 177.54(18) . . . . ?
Cl2 C7 N2 Cl1 -2.0(3) . . . . ?
C5 C6 N2 C7 179.1(3) . . . . ?
C1 C6 N2 C7 0.0(3) . . . . ?
C5 C6 N2 Cl1 1.9(4) . . . . ?
C1 C6 N2 Cl1 -177.21(17) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2173227'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University of Rennes 
France
;
_audit_update_record             
;
2022-05-17 deposited with the CCDC.	2022-08-24 downloaded from the CCDC.
;

_audit_creation_date             2022-05-16T10:42:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C7 H4 Br Cl N2'
_chemical_formula_moiety         'C7 H4 Br Cl N2'
_chemical_formula_weight         231.48

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a b'
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, z'

_cell_length_a                   9.3593(11)
_cell_length_b                   12.3411(18)
_cell_length_c                   13.8369(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1598.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1354
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      22.51
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.924
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_T_max  0.806

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.3869  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.049796
_diffrn_orient_matrix_ub_12      0.060412
_diffrn_orient_matrix_ub_13      0.03443
_diffrn_orient_matrix_ub_21      -0.026539
_diffrn_orient_matrix_ub_22      -0.032943
_diffrn_orient_matrix_ub_23      0.063541
_diffrn_orient_matrix_ub_31      0.09073
_diffrn_orient_matrix_ub_32      -0.042792
_diffrn_orient_matrix_ub_33      -0.00031
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_number            6487
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.944
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_reflns_Friedel_coverage         0
_reflns_number_total             1807
_reflns_number_gt                1085
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1807
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.047
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0728
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.54
_refine_diff_density_rms         0.098

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.0814(4) 0.1987(3) 0.1063(3) 0.0281(10) Uani 1 1 d . . . . .
C2 C 0.0780(4) 0.0871(3) 0.1146(3) 0.0292(10) Uani 1 1 d . . . . .
C3 C -0.0151(4) 0.0387(4) 0.1790(3) 0.0424(12) Uani 1 1 d . . . . .
H3 H -0.0189 -0.0363 0.1858 0.051 Uiso 1 1 calc R U . . .
C4 C -0.1021(4) 0.1053(4) 0.2328(3) 0.0496(13) Uani 1 1 d . . . . .
H4 H -0.1673 0.0749 0.2757 0.06 Uiso 1 1 calc R U . . .
C5 C -0.0944(4) 0.2170(5) 0.2243(4) 0.0500(13) Uani 1 1 d . . . . .
H5 H -0.153 0.2593 0.2632 0.06 Uiso 1 1 calc R U . . .
C6 C -0.0037(4) 0.2677(4) 0.1605(3) 0.0411(12) Uani 1 1 d . . . . .
H6 H 0.0003 0.3427 0.1542 0.049 Uiso 1 1 calc R U . . .
C7 C 0.2310(4) 0.1206(3) 0.0050(3) 0.0316(10) Uani 1 1 d . . . . .
N1 N 0.1793(3) 0.2191(3) 0.0333(3) 0.0323(9) Uani 1 1 d . . . . .
N2 N 0.1749(3) 0.0397(3) 0.0506(3) 0.0343(9) Uani 1 1 d . . . . .
Cl1 Cl 0.23780(9) 0.34218(8) -0.00365(8) 0.0354(3) Uani 1 1 d . . . . .
Br1 Br 0.36623(4) 0.11049(4) -0.09300(3) 0.04620(19) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.382(5) . ?
C1 N1 1.387(5) . ?
C1 C6 1.387(5) . ?
C2 C3 1.383(5) . ?
C2 N2 1.396(5) . ?
C3 C4 1.376(6) . ?
C3 H3 0.93 . ?
C4 C5 1.384(7) . ?
C4 H4 0.93 . ?
C5 C6 1.376(6) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 N2 1.292(5) . ?
C7 N1 1.366(5) . ?
C7 Br1 1.859(4) . ?
N1 Cl1 1.693(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 104.9(3) . . ?
C2 C1 C6 123.6(4) . . ?
N1 C1 C6 131.4(4) . . ?
C1 C2 C3 120.0(4) . . ?
C1 C2 N2 110.4(3) . . ?
C3 C2 N2 129.6(4) . . ?
C4 C3 C2 117.6(4) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 121.2(4) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 122.7(4) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C1 115.0(4) . . ?
C5 C6 H6 122.5 . . ?
C1 C6 H6 122.5 . . ?
N2 C7 N1 113.8(4) . . ?
N2 C7 Br1 125.5(3) . . ?
N1 C7 Br1 120.7(3) . . ?
C7 N1 C1 106.3(3) . . ?
C7 N1 Cl1 126.7(3) . . ?
C1 N1 Cl1 126.6(3) . . ?
C7 N2 C2 104.5(3) . . ?

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
N1 C1 C2 C3 -177.0(4) . . . . ?
C6 C1 C2 C3 0.8(6) . . . . ?
N1 C1 C2 N2 1.9(4) . . . . ?
C6 C1 C2 N2 179.7(4) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
N2 C2 C3 C4 -178.6(4) . . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?
C3 C4 C5 C6 1.9(7) . . . . ?
C4 C5 C6 C1 -0.9(6) . . . . ?
C2 C1 C6 C5 -0.4(6) . . . . ?
N1 C1 C6 C5 176.9(4) . . . . ?
N2 C7 N1 C1 1.3(5) . . . . ?
Br1 C7 N1 C1 179.7(3) . . . . ?
N2 C7 N1 Cl1 174.5(3) . . . . ?
Br1 C7 N1 Cl1 -7.0(5) . . . . ?
C2 C1 N1 C7 -1.8(4) . . . . ?
C6 C1 N1 C7 -179.4(4) . . . . ?
C2 C1 N1 Cl1 -175.1(3) . . . . ?
C6 C1 N1 Cl1 7.3(6) . . . . ?
N1 C7 N2 C2 -0.1(5) . . . . ?
Br1 C7 N2 C2 -178.5(3) . . . . ?
C1 C2 N2 C7 -1.1(4) . . . . ?
C3 C2 N2 C7 177.6(4) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2173225'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University of Rennes 
France
;
_audit_update_record             
;
2022-05-17 deposited with the CCDC.	2022-08-24 downloaded from the CCDC.
;

_audit_creation_date             2022-05-16T10:20:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C8 H5 Cl3 N2'
_chemical_formula_moiety         'C8 H5 Cl3 N2'
_chemical_formula_weight         235.49

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.9218(4)
_cell_length_b                   12.4195(11)
_cell_length_c                   18.9195(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.528(3)
_cell_angle_gamma                90
_cell_volume                     918.63(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8301
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.43
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_T_max  0.954

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.6563  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.091622
_diffrn_orient_matrix_ub_12      0.042139
_diffrn_orient_matrix_ub_13      0.039367
_diffrn_orient_matrix_ub_21      -0.213412
_diffrn_orient_matrix_ub_22      -0.044371
_diffrn_orient_matrix_ub_23      -0.004208
_diffrn_orient_matrix_ub_31      0.107171
_diffrn_orient_matrix_ub_32      -0.052333
_diffrn_orient_matrix_ub_33      0.035267
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_number            19525
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.712
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             2099
_reflns_number_gt                1740
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'



#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom



#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+0.7891P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2099
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.3148(5) 0.26589(16) 0.68969(11) 0.0283(4) Uani 1 1 d . . . . .
C2 C 0.4615(5) 0.19231(17) 0.64625(11) 0.0323(5) Uani 1 1 d . . . . .
H2 H 0.5401 0.1261 0.6637 0.039 Uiso 1 1 calc R U . . .
C3 C 0.4878(5) 0.22019(17) 0.57627(11) 0.0312(5) Uani 1 1 d . . . . .
C4 C 0.3732(5) 0.32055(17) 0.54986(11) 0.0316(5) Uani 1 1 d . . . . .
C5 C 0.2285(5) 0.39524(16) 0.59255(11) 0.0309(5) Uani 1 1 d . . . . .
H5 H 0.1516 0.4618 0.5754 0.037 Uiso 1 1 calc R U . . .
C6 C 0.2047(5) 0.36517(16) 0.66234(11) 0.0276(4) Uani 1 1 d . . . . .
C7 C 0.1070(5) 0.34813(18) 0.77652(11) 0.0319(5) Uani 1 1 d . . . . .
C8 C -0.0109(7) 0.3781(2) 0.84647(12) 0.0443(6) Uani 1 1 d . . . . .
H8A H -0.0416 0.3141 0.8737 0.066 Uiso 1 1 calc R U . . .
H8B H -0.2242 0.416 0.8397 0.066 Uiso 1 1 calc R U . . .
H8C H 0.1568 0.4234 0.8713 0.066 Uiso 1 1 calc R U . . .
N1 N 0.2516(5) 0.25749(15) 0.76095(9) 0.0339(4) Uani 1 1 d . . . . .
N2 N 0.0723(5) 0.41607(14) 0.71876(9) 0.0313(4) Uani 1 1 d . . . . .
Cl1 Cl 0.66285(17) 0.12776(5) 0.52118(3) 0.04721(18) Uani 1 1 d . . . . .
Cl2 Cl 0.40619(19) 0.35212(5) 0.46154(3) 0.04972(19) Uani 1 1 d . . . . .
Cl3 Cl -0.07464(14) 0.54462(4) 0.71755(3) 0.03590(15) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.384(3) . ?
C1 C6 1.392(3) . ?
C1 N1 1.394(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.93 . ?
C3 C4 1.403(3) . ?
C3 Cl1 1.729(2) . ?
C4 C5 1.381(3) . ?
C4 Cl2 1.731(2) . ?
C5 C6 1.382(3) . ?
C5 H5 0.93 . ?
C6 N2 1.377(3) . ?
C7 N1 1.305(3) . ?
C7 N2 1.379(3) . ?
C7 C8 1.483(3) . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
N2 Cl3 1.6969(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.68(19) . . ?
C2 C1 N1 129.70(19) . . ?
C6 C1 N1 110.62(18) . . ?
C3 C2 C1 118.03(19) . . ?
C3 C2 H2 121 . . ?
C1 C2 H2 121 . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 Cl1 118.36(17) . . ?
C4 C3 Cl1 120.42(17) . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 Cl2 118.54(17) . . ?
C3 C4 Cl2 119.90(17) . . ?
C4 C5 C6 116.03(19) . . ?
C4 C5 H5 122 . . ?
C6 C5 H5 122 . . ?
N2 C6 C5 132.40(19) . . ?
N2 C6 C1 104.08(17) . . ?
C5 C6 C1 123.50(19) . . ?
N1 C7 N2 111.50(19) . . ?
N1 C7 C8 126.1(2) . . ?
N2 C7 C8 122.4(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 N1 C1 105.51(17) . . ?
C6 N2 C7 108.28(17) . . ?
C6 N2 Cl3 124.75(15) . . ?
C7 N2 Cl3 126.77(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.1(3) . . . . ?
N1 C1 C2 C3 178.6(2) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C2 C3 Cl1 -178.71(16) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
Cl1 C3 C4 C5 179.17(16) . . . . ?
C2 C3 C4 Cl2 -179.30(16) . . . . ?
Cl1 C3 C4 Cl2 0.1(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
Cl2 C4 C5 C6 179.19(16) . . . . ?
C4 C5 C6 N2 -178.4(2) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C2 C1 C6 N2 179.42(18) . . . . ?
N1 C1 C6 N2 -0.3(2) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
N1 C1 C6 C5 -178.69(19) . . . . ?
N2 C7 N1 C1 -0.1(2) . . . . ?
C8 C7 N1 C1 179.7(2) . . . . ?
C2 C1 N1 C7 -179.4(2) . . . . ?
C6 C1 N1 C7 0.2(2) . . . . ?
C5 C6 N2 C7 178.4(2) . . . . ?
C1 C6 N2 C7 0.2(2) . . . . ?
C5 C6 N2 Cl3 -6.4(3) . . . . ?
C1 C6 N2 Cl3 175.40(14) . . . . ?
N1 C7 N2 C6 -0.1(2) . . . . ?
C8 C7 N2 C6 -179.9(2) . . . . ?
N1 C7 N2 Cl3 -175.14(15) . . . . ?
C8 C7 N2 Cl3 5.1(3) . . . . ?



# END of CIF
