# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1034733'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_date             2012-12-17T06:25:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 (2-chloro-4-nitrobenzoic acid)(2-bromopyridine)  
;
_chemical_formula_moiety         'C7 H4 Cl N O4, C5 H4 Br N'
_chemical_formula_sum            'C12 H8 Br Cl N2 O4'
_chemical_formula_weight         359.56

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2583(7)
_cell_length_b                   9.0938(7)
_cell_length_c                   9.1385(7)
_cell_angle_alpha                88.094(5)
_cell_angle_beta                 77.372(5)
_cell_angle_gamma                80.171(5)
_cell_volume                     659.86(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3260
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.07

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.81
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 2 0.27
1 -2 1 0.258
-1 2 -1 0.191
2 1 -2 0.061
-2 -1 2 0.059
1 1 1 0.13
-1 -1 -1 0.121
0 -1 0 0.216

_exptl_special_details           
;
  Absorption corrections were made using the program SADABS 
(Sheldrick, 1996)
;

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

_exptl_absorpt_coefficient_mu    3.331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.2703
_exptl_absorpt_correction_T_max  0.6867

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0803
_diffrn_reflns_number            8835
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             3168
_reflns_number_gt                2394
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX3 (Bruker, 2007)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0908P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3168
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1446
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.282
_refine_diff_density_min         -0.59
_refine_diff_density_rms         0.133

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2198(4) 0.5464(4) 0.4859(4) 0.0384(7) Uani 1 1 d . . .
C2 C 0.1315(4) 0.6928(4) 0.5025(4) 0.0399(7) Uani 1 1 d . . .
C3 C 0.0509(5) 0.7585(4) 0.3921(4) 0.0433(8) Uani 1 1 d . . .
H3 H -0.0072 0.8585 0.4027 0.052 Uiso 1 1 calc R . .
C4 C 0.0571(4) 0.6760(4) 0.2680(4) 0.0414(7) Uani 1 1 d . . .
C5 C 0.1388(5) 0.5292(4) 0.2476(4) 0.0431(8) Uani 1 1 d . . .
H5 H 0.1395 0.4737 0.1611 0.052 Uiso 1 1 calc R . .
C6 C 0.2190(4) 0.4671(4) 0.3581(4) 0.0413(7) Uani 1 1 d . . .
H6 H 0.2757 0.3667 0.3468 0.05 Uiso 1 1 calc R . .
C7 C 0.3157(4) 0.4747(4) 0.5986(4) 0.0408(7) Uani 1 1 d . . .
N1 N -0.0309(4) 0.7452(4) 0.1536(4) 0.0484(7) Uani 1 1 d . . .
O1 O 0.3303(3) 0.3270(3) 0.5994(3) 0.0475(6) Uani 1 1 d . . .
H1 H 0.395(6) 0.284(5) 0.668(6) 0.057(12) Uiso 1 1 d . . .
O2 O 0.3772(4) 0.5429(3) 0.6754(3) 0.0519(6) Uani 1 1 d . . .
O3 O -0.0419(5) 0.6693(4) 0.0510(4) 0.0744(9) Uani 1 1 d . . .
O4 O -0.0908(4) 0.8774(3) 0.1672(4) 0.0642(8) Uani 1 1 d . . .
Cl1 Cl 0.10926(14) 0.79801(11) 0.66169(11) 0.0578(3) Uani 1 1 d . . .
C8 C 0.6121(4) 0.0875(4) 0.8021(4) 0.0408(7) Uani 1 1 d . . .
C9 C 0.6994(5) 0.0411(4) 0.9122(4) 0.0464(8) Uani 1 1 d . . .
H9 H 0.7742 -0.0515 0.9045 0.056 Uiso 1 1 calc R . .
C10 C 0.6739(5) 0.1346(4) 1.0344(4) 0.0485(8) Uani 1 1 d . . .
H10 H 0.7301 0.106 1.1138 0.058 Uiso 1 1 calc R . .
C11 C 0.5672(6) 0.2684(4) 1.0406(4) 0.0508(9) Uani 1 1 d . . .
H11 H 0.5499 0.3345 1.1229 0.061 Uiso 1 1 calc R . .
C12 C 0.4855(5) 0.3050(4) 0.9241(4) 0.0499(9) Uani 1 1 d . . .
H12 H 0.4106 0.3974 0.9289 0.06 Uiso 1 1 calc R . .
N2 N 0.5071(4) 0.2160(3) 0.8041(3) 0.0436(7) Uani 1 1 d . . .
Br1 Br 0.63580(5) -0.03460(4) 0.63335(4) 0.0555(2) 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 C6 1.394(5) . ?
C1 C2 1.400(5) . ?
C1 C7 1.500(5) . ?
C2 C3 1.391(5) . ?
C2 Cl1 1.726(3) . ?
C3 C4 1.368(5) . ?
C3 H3 0.95 . ?
C4 C5 1.388(5) . ?
C4 N1 1.466(5) . ?
C5 C6 1.380(5) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 O2 1.195(4) . ?
C7 O1 1.328(4) . ?
N1 O3 1.210(4) . ?
N1 O4 1.219(4) . ?
O1 H1 0.95(5) . ?
C8 N2 1.329(5) . ?
C8 C9 1.376(5) . ?
C8 Br1 1.886(3) . ?
C9 C10 1.383(5) . ?
C9 H9 0.95 . ?
C10 C11 1.370(6) . ?
C10 H10 0.95 . ?
C11 C12 1.383(6) . ?
C11 H11 0.95 . ?
C12 N2 1.347(5) . ?
C12 H12 0.95 . ?

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
C6 C1 C2 117.9(3) . . ?
C6 C1 C7 119.8(3) . . ?
C2 C1 C7 122.3(3) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 Cl1 116.6(3) . . ?
C1 C2 Cl1 122.5(3) . . ?
C4 C3 C2 118.5(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 123.1(3) . . ?
C3 C4 N1 118.1(3) . . ?
C5 C4 N1 118.8(3) . . ?
C6 C5 C4 117.2(3) . . ?
C6 C5 H5 121.4 . . ?
C4 C5 H5 121.4 . . ?
C5 C6 C1 122.4(3) . . ?
C5 C6 H6 118.8 . . ?
C1 C6 H6 118.8 . . ?
O2 C7 O1 123.8(3) . . ?
O2 C7 C1 123.5(3) . . ?
O1 C7 C1 112.6(3) . . ?
O3 N1 O4 123.0(3) . . ?
O3 N1 C4 119.0(3) . . ?
O4 N1 C4 118.0(3) . . ?
C7 O1 H1 111(3) . . ?
N2 C8 C9 124.7(3) . . ?
N2 C8 Br1 115.0(3) . . ?
C9 C8 Br1 120.3(3) . . ?
C8 C9 C10 117.4(3) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
C11 C10 C9 119.7(4) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 118.5(4) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
N2 C12 C11 123.1(4) . . ?
N2 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
C8 N2 C12 116.5(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
C6 C1 C2 C3 -2.3(5) . . . . ?
C7 C1 C2 C3 176.7(3) . . . . ?
C6 C1 C2 Cl1 175.0(3) . . . . ?
C7 C1 C2 Cl1 -5.9(5) . . . . ?
C1 C2 C3 C4 1.2(5) . . . . ?
Cl1 C2 C3 C4 -176.3(3) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C2 C3 C4 N1 178.9(3) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
N1 C4 C5 C6 -179.4(3) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C2 C1 C6 C5 1.8(5) . . . . ?
C7 C1 C6 C5 -177.3(3) . . . . ?
C6 C1 C7 O2 150.4(4) . . . . ?
C2 C1 C7 O2 -28.7(5) . . . . ?
C6 C1 C7 O1 -27.1(4) . . . . ?
C2 C1 C7 O1 153.8(3) . . . . ?
C3 C4 N1 O3 -172.3(4) . . . . ?
C5 C4 N1 O3 6.1(5) . . . . ?
C3 C4 N1 O4 7.2(5) . . . . ?
C5 C4 N1 O4 -174.4(3) . . . . ?
N2 C8 C9 C10 0.8(6) . . . . ?
Br1 C8 C9 C10 -178.7(3) . . . . ?
C8 C9 C10 C11 -1.1(6) . . . . ?
C9 C10 C11 C12 1.1(6) . . . . ?
C10 C11 C12 N2 -0.7(6) . . . . ?
C9 C8 N2 C12 -0.4(5) . . . . ?
Br1 C8 N2 C12 179.1(3) . . . . ?
C11 C12 N2 C8 0.4(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N2 0.95(5) 1.74(5) 2.686(4) 176(4) .
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1034735'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_date             2012-11-02T07:15:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 (2-chloro-4-nitrobenzoic acid)(3-amino-2-bromopyridine)  
;
_chemical_formula_moiety         'C7 H4 Cl N O4, C5 H5 Br N2'
_chemical_formula_sum            'C12 H9 Br Cl N3 O4'
_chemical_formula_weight         374.58

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8994(3)
_cell_length_b                   11.9370(4)
_cell_length_c                   13.4905(6)
_cell_angle_alpha                110.222(2)
_cell_angle_beta                 96.641(2)
_cell_angle_gamma                107.0590(10)
_cell_volume                     1387.59(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8172
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.01

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.676
_exptl_crystal_size_mid          0.383
_exptl_crystal_size_min          0.122
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.151
-2 1 0 0.074
2 0 -1 0.06
-2 0 1 0.061
0 2 -1 0.105
0 -1 1 0.236
0 1 -1 0.148
0 0 1 0.293
0 1 1 0.246
0 -1 -1 0.179

_exptl_special_details           
;
 Numerical integration absorption corrections based on indexed crystal faces
were applied using the XPREP routine (Bruker, 2004)
;

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

_exptl_absorpt_coefficient_mu    3.174
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 2004)'
_exptl_absorpt_correction_T_min  0.2945
_exptl_absorpt_correction_T_max  0.7011

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_number            25750
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             6697
_reflns_number_gt                5150
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX3 (Bruker, 2007)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0688P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6697
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.009
_refine_diff_density_min         -0.881
_refine_diff_density_rms         0.117

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9496(3) 0.9131(2) 0.27432(19) 0.0253(5) Uani 1 1 d . . .
C2 C 0.9692(3) 0.9592(2) 0.1928(2) 0.0253(5) Uani 1 1 d . . .
C3 C 0.8512(3) 0.9363(2) 0.1129(2) 0.0271(5) Uani 1 1 d . . .
H3 H 0.8643 0.9668 0.0571 0.032 Uiso 1 1 calc R . .
C4 C 0.7141(3) 0.8679(2) 0.1165(2) 0.0270(5) Uani 1 1 d . . .
C5 C 0.6898(3) 0.8186(2) 0.1939(2) 0.0304(6) Uani 1 1 d . . .
H5A H 0.5942 0.7703 0.1933 0.036 Uiso 1 1 calc R . .
C6 C 0.8092(3) 0.8418(2) 0.2727(2) 0.0292(5) Uani 1 1 d . . .
H6 H 0.795 0.8085 0.3268 0.035 Uiso 1 1 calc R . .
C7 C 1.0726(3) 0.9395(3) 0.3660(2) 0.0299(6) Uani 1 1 d . . .
N1 N 0.5886(3) 0.8507(2) 0.03444(19) 0.0381(6) Uani 1 1 d . . .
O1 O 1.1824(2) 1.0337(2) 0.40213(17) 0.0450(5) Uani 1 1 d . . .
O2 O 1.0428(3) 0.8482(2) 0.4025(2) 0.0432(5) Uani 1 1 d . . .
H2 H 1.088(5) 0.873(4) 0.453(4) 0.076(16) Uiso 1 1 d . . .
O3 O 0.6131(3) 0.8953(3) -0.0328(2) 0.0621(7) Uani 1 1 d . . .
O4 O 0.4663(2) 0.7926(2) 0.03944(17) 0.0480(6) Uani 1 1 d . . .
Cl1 Cl 1.13777(7) 1.04400(7) 0.18320(5) 0.03501(16) Uani 1 1 d . . .
C8 C 0.5027(3) 0.3843(2) 0.35590(18) 0.0257(5) Uani 1 1 d . . .
C9 C 0.6518(3) 0.4427(2) 0.40368(19) 0.0259(5) Uani 1 1 d . . .
C10 C 0.7109(3) 0.4275(2) 0.49443(19) 0.0281(5) Uani 1 1 d . . .
H10 H 0.8124 0.4665 0.5271 0.034 Uiso 1 1 calc R . .
C11 C 0.6179(3) 0.3540(2) 0.53618(19) 0.0294(6) Uani 1 1 d . . .
C12 C 0.4710(3) 0.2965(2) 0.4924(2) 0.0310(6) Uani 1 1 d . . .
H12 H 0.4101 0.247 0.5231 0.037 Uiso 1 1 calc R . .
C13 C 0.4138(3) 0.3127(2) 0.4019(2) 0.0299(6) Uani 1 1 d . . .
H13 H 0.3119 0.2743 0.3706 0.036 Uiso 1 1 calc R . .
C14 C 0.4361(3) 0.3912(3) 0.2521(2) 0.0307(6) Uani 1 1 d . . .
N2 N 0.6827(3) 0.3391(2) 0.63286(19) 0.0409(6) Uani 1 1 d . . .
O5 O 0.3058(2) 0.3961(2) 0.25026(16) 0.0350(5) Uani 1 1 d . . .
H5 H 0.285(5) 0.400(4) 0.203(3) 0.065(14) Uiso 1 1 d . . .
O6 O 0.4965(3) 0.3869(3) 0.17919(17) 0.0578(7) Uani 1 1 d . . .
O7 O 0.6007(3) 0.2906(2) 0.67903(19) 0.0617(7) Uani 1 1 d . . .
O8 O 0.8154(3) 0.3786(3) 0.66229(18) 0.0573(7) Uani 1 1 d . . .
Cl2 Cl 0.76851(8) 0.54213(7) 0.35862(6) 0.04406(19) Uani 1 1 d . . .
C15 C 1.2330(3) 0.8437(2) 0.64455(19) 0.0241(5) Uani 1 1 d . . .
C16 C 1.3412(3) 0.8598(2) 0.73025(19) 0.0244(5) Uani 1 1 d . . .
C17 C 1.4807(3) 0.9437(3) 0.7407(2) 0.0289(5) Uani 1 1 d . . .
H17 H 1.5601 0.9596 0.7968 0.035 Uiso 1 1 calc R . .
C18 C 1.5023(3) 1.0026(3) 0.6695(2) 0.0337(6) Uani 1 1 d . . .
H18 H 1.5967 1.0589 0.6762 0.04 Uiso 1 1 calc R . .
C19 C 1.3869(3) 0.9802(3) 0.5882(2) 0.0333(6) Uani 1 1 d . . .
H19 H 1.4024 1.0226 0.5402 0.04 Uiso 1 1 calc R . .
N3 N 1.2532(2) 0.8994(2) 0.57589(16) 0.0274(4) Uani 1 1 d . . .
N4 N 1.3134(3) 0.8029(3) 0.80149(19) 0.0340(5) Uani 1 1 d . . .
H4A H 1.245(4) 0.737(3) 0.783(3) 0.037(9) Uiso 1 1 d . . .
H4B H 1.387(4) 0.806(3) 0.849(3) 0.039(8) Uiso 1 1 d . . .
Br1 Br 1.04031(3) 0.73450(3) 0.62512(2) 0.03658(10) Uani 1 1 d . . .
C20 C 0.0636(3) 0.3471(2) 0.0110(2) 0.0282(5) Uani 1 1 d . . .
C21 C 0.0045(3) 0.3520(2) -0.0863(2) 0.0289(5) Uani 1 1 d . . .
C22 C 0.1004(3) 0.4245(3) -0.1279(2) 0.0344(6) Uani 1 1 d . . .
H22 H 0.0664 0.4314 -0.1935 0.041 Uiso 1 1 calc R . .
C23 C 0.2455(3) 0.4863(3) -0.0726(2) 0.0385(7) Uani 1 1 d . . .
H23 H 0.3085 0.5341 -0.1034 0.046 Uiso 1 1 calc R . .
C24 C 0.3075(4) 0.4840(3) 0.0264(2) 0.0350(7) Uani 1 1 d . . .
H24 H 0.4071 0.5285 0.064 0.042 Uiso 1 1 calc R . .
N5 N 0.2015(3) 0.4058(2) 0.06354(18) 0.0331(5) Uani 1 1 d . . .
N6 N -0.1395(3) 0.2838(3) -0.1406(2) 0.0415(6) Uani 1 1 d . . .
H6A H -0.199(5) 0.257(4) -0.100(4) 0.082(14) Uiso 1 1 d . . .
H6B H -0.166(5) 0.310(4) -0.183(4) 0.085(16) Uiso 1 1 d . . .
Br2 Br -0.05895(3) 0.25242(3) 0.07389(2) 0.04053(10) 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 C6 1.394(4) . ?
C1 C2 1.399(4) . ?
C1 C7 1.507(3) . ?
C2 C3 1.385(3) . ?
C2 Cl1 1.725(3) . ?
C3 C4 1.379(4) . ?
C3 H3 0.95 . ?
C4 C5 1.376(4) . ?
C4 N1 1.479(3) . ?
C5 C6 1.384(4) . ?
C5 H5A 0.95 . ?
C6 H6 0.95 . ?
C7 O1 1.210(3) . ?
C7 O2 1.316(3) . ?
N1 O3 1.215(3) . ?
N1 O4 1.228(3) . ?
O2 H2 0.68(5) . ?
C8 C13 1.393(4) . ?
C8 C9 1.395(4) . ?
C8 C14 1.516(3) . ?
C9 C10 1.387(3) . ?
C9 Cl2 1.723(3) . ?
C10 C11 1.387(4) . ?
C10 H10 0.95 . ?
C11 C12 1.368(4) . ?
C11 N2 1.476(3) . ?
C12 C13 1.385(4) . ?
C12 H12 0.95 . ?
C13 H13 0.95 . ?
C14 O6 1.203(3) . ?
C14 O5 1.306(3) . ?
N2 O7 1.214(4) . ?
N2 O8 1.222(4) . ?
O5 H5 0.67(4) . ?
C15 N3 1.316(3) . ?
C15 C16 1.400(3) . ?
C15 Br1 1.896(2) . ?
C16 N4 1.365(3) . ?
C16 C17 1.406(4) . ?
C17 C18 1.375(4) . ?
C17 H17 0.95 . ?
C18 C19 1.381(4) . ?
C18 H18 0.95 . ?
C19 N3 1.341(3) . ?
C19 H19 0.95 . ?
N4 H4A 0.81(3) . ?
N4 H4B 0.90(3) . ?
C20 N5 1.315(3) . ?
C20 C21 1.402(3) . ?
C20 Br2 1.888(3) . ?
C21 N6 1.377(4) . ?
C21 C22 1.392(4) . ?
C22 C23 1.384(4) . ?
C22 H22 0.95 . ?
C23 C24 1.417(4) . ?
C23 H23 0.95 . ?
C24 N5 1.447(4) . ?
C24 H24 0.95 . ?
N6 H6A 0.91(5) . ?
N6 H6B 0.79(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.7(2) . . ?
C6 C1 C7 118.1(2) . . ?
C2 C1 C7 123.2(2) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 Cl1 116.1(2) . . ?
C1 C2 Cl1 123.20(19) . . ?
C4 C3 C2 118.3(2) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 123.0(2) . . ?
C5 C4 N1 119.3(2) . . ?
C3 C4 N1 117.6(2) . . ?
C4 C5 C6 117.8(2) . . ?
C4 C5 H5A 121.1 . . ?
C6 C5 H5A 121.1 . . ?
C5 C6 C1 121.4(2) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O1 C7 O2 125.1(2) . . ?
O1 C7 C1 124.0(2) . . ?
O2 C7 C1 110.9(2) . . ?
O3 N1 O4 124.5(2) . . ?
O3 N1 C4 118.0(2) . . ?
O4 N1 C4 117.5(2) . . ?
C7 O2 H2 107(4) . . ?
C13 C8 C9 119.1(2) . . ?
C13 C8 C14 119.2(2) . . ?
C9 C8 C14 121.7(2) . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 Cl2 117.1(2) . . ?
C8 C9 Cl2 122.46(19) . . ?
C11 C10 C9 118.3(2) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C12 C11 C10 123.1(2) . . ?
C12 C11 N2 119.4(3) . . ?
C10 C11 N2 117.5(3) . . ?
C11 C12 C13 117.9(3) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C12 C13 C8 121.3(3) . . ?
C12 C13 H13 119.3 . . ?
C8 C13 H13 119.3 . . ?
O6 C14 O5 125.1(2) . . ?
O6 C14 C8 122.5(2) . . ?
O5 C14 C8 112.3(2) . . ?
O7 N2 O8 124.4(3) . . ?
O7 N2 C11 117.9(3) . . ?
O8 N2 C11 117.8(3) . . ?
C14 O5 H5 105(4) . . ?
N3 C15 C16 125.3(2) . . ?
N3 C15 Br1 116.48(17) . . ?
C16 C15 Br1 118.19(19) . . ?
N4 C16 C15 123.0(2) . . ?
N4 C16 C17 122.0(2) . . ?
C15 C16 C17 115.0(2) . . ?
C18 C17 C16 119.9(2) . . ?
C18 C17 H17 120 . . ?
C16 C17 H17 120 . . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18 120 . . ?
C19 C18 H18 120 . . ?
N3 C19 C18 121.0(2) . . ?
N3 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C15 N3 C19 118.7(2) . . ?
C16 N4 H4A 120(2) . . ?
C16 N4 H4B 120(2) . . ?
H4A N4 H4B 111(3) . . ?
N5 C20 C21 124.1(3) . . ?
N5 C20 Br2 116.48(18) . . ?
C21 C20 Br2 119.4(2) . . ?
N6 C21 C22 121.8(2) . . ?
N6 C21 C20 121.6(3) . . ?
C22 C21 C20 116.6(3) . . ?
C23 C22 C21 119.4(2) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 125.1(3) . . ?
C22 C23 H23 117.4 . . ?
C24 C23 H23 117.4 . . ?
C23 C24 N5 112.1(3) . . ?
C23 C24 H24 123.9 . . ?
N5 C24 H24 123.9 . . ?
C20 N5 C24 122.7(2) . . ?
C21 N6 H6A 115(3) . . ?
C21 N6 H6B 112(3) . . ?
H6A N6 H6B 121(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
C6 C1 C2 C3 1.0(4) . . . . ?
C7 C1 C2 C3 -177.4(2) . . . . ?
C6 C1 C2 Cl1 -177.83(19) . . . . ?
C7 C1 C2 Cl1 3.8(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
Cl1 C2 C3 C4 179.47(19) . . . . ?
C2 C3 C4 C5 -1.8(4) . . . . ?
C2 C3 C4 N1 176.5(2) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
N1 C4 C5 C6 -176.9(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C2 C1 C6 C5 -1.4(4) . . . . ?
C7 C1 C6 C5 177.0(2) . . . . ?
C6 C1 C7 O1 -150.2(3) . . . . ?
C2 C1 C7 O1 28.1(4) . . . . ?
C6 C1 C7 O2 28.3(3) . . . . ?
C2 C1 C7 O2 -153.3(2) . . . . ?
C5 C4 N1 O3 179.9(3) . . . . ?
C3 C4 N1 O3 1.5(4) . . . . ?
C5 C4 N1 O4 0.2(4) . . . . ?
C3 C4 N1 O4 -178.2(2) . . . . ?
C13 C8 C9 C10 1.3(4) . . . . ?
C14 C8 C9 C10 -175.7(2) . . . . ?
C13 C8 C9 Cl2 -175.32(19) . . . . ?
C14 C8 C9 Cl2 7.8(3) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
Cl2 C9 C10 C11 176.32(19) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C9 C10 C11 N2 -179.9(2) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
N2 C11 C12 C13 179.8(2) . . . . ?
C11 C12 C13 C8 0.6(4) . . . . ?
C9 C8 C13 C12 -1.3(4) . . . . ?
C14 C8 C13 C12 175.7(2) . . . . ?
C13 C8 C14 O6 -139.6(3) . . . . ?
C9 C8 C14 O6 37.3(4) . . . . ?
C13 C8 C14 O5 37.4(3) . . . . ?
C9 C8 C14 O5 -145.7(2) . . . . ?
C12 C11 N2 O7 -9.8(4) . . . . ?
C10 C11 N2 O7 169.8(2) . . . . ?
C12 C11 N2 O8 171.6(2) . . . . ?
C10 C11 N2 O8 -8.9(4) . . . . ?
N3 C15 C16 N4 177.8(2) . . . . ?
Br1 C15 C16 N4 -1.5(3) . . . . ?
N3 C15 C16 C17 0.3(4) . . . . ?
Br1 C15 C16 C17 -179.01(17) . . . . ?
N4 C16 C17 C18 -177.4(2) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C17 C18 C19 N3 -1.2(4) . . . . ?
C16 C15 N3 C19 -1.1(4) . . . . ?
Br1 C15 N3 C19 178.24(18) . . . . ?
C18 C19 N3 C15 1.5(4) . . . . ?
N5 C20 C21 N6 177.0(3) . . . . ?
Br2 C20 C21 N6 -3.6(4) . . . . ?
N5 C20 C21 C22 -0.1(4) . . . . ?
Br2 C20 C21 C22 179.37(19) . . . . ?
N6 C21 C22 C23 -177.0(3) . . . . ?
C20 C21 C22 C23 0.1(4) . . . . ?
C21 C22 C23 C24 -0.8(4) . . . . ?
C22 C23 C24 N5 1.4(4) . . . . ?
C21 C20 N5 C24 0.8(4) . . . . ?
Br2 C20 N5 C24 -178.68(18) . . . . ?
C23 C24 N5 C20 -1.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N3 0.68(5) 2.06(5) 2.706(3) 159(5) .
O5 H5 N5 0.67(4) 2.00(4) 2.664(3) 174(5) .
N4 H4A Br2 0.81(3) 2.81(3) 3.221(2) 113(3) 2_666
N4 H4B O3 0.90(3) 2.30(3) 3.139(3) 156(3) 1_656
N6 H6A Br2 0.91(5) 2.61(4) 3.089(3) 113(3) .
N6 H6B O7 0.79(5) 2.69(5) 3.370(4) 144(4) 1_454
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1034737'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_date             2012-11-02T13:38:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 (2-chloro-4-nitrobenzoic acid)(3-amino-2-chloropyridine) 
;
_chemical_formula_moiety         'C7 H4 Cl N O4, C5 H5 Cl N2'
_chemical_formula_sum            'C12 H9 Cl2 N3 O4'
_chemical_formula_weight         330.12

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'
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                   7.0984(2)
_cell_length_b                   24.0534(7)
_cell_length_c                   15.7748(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.424(2)
_cell_angle_gamma                90
_cell_volume                     2688.59(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      28.08

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

_exptl_crystal_description       needles
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.761
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.076
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 0 1 0.367
2 0 -1 0.268
0 -2 -1 0.038
0 2 1 0.026
0 -1 1 0.045
0 1 -1 0.037

_exptl_special_details           
;
 Numerical integration absorption corrections based on indexed crystal faces
were applied using the XPREP routine (Bruker, 2004)
;

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

_exptl_absorpt_coefficient_mu    0.502
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 2004)'
_exptl_absorpt_correction_T_min  0.8326
_exptl_absorpt_correction_T_max  0.9791

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_number            44874
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             6484
_reflns_number_gt                4799
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX3 (Bruker, 2007)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0436P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6484
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.29
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4273(2) 0.23070(6) 0.93206(10) 0.0225(3) Uani 1 1 d . . .
C2 C 0.4589(2) 0.19119(6) 0.99609(10) 0.0225(3) Uani 1 1 d . . .
C3 C 0.4641(2) 0.20615(6) 1.08083(10) 0.0248(3) Uani 1 1 d . . .
H3 H 0.4875 0.1793 1.1243 0.03 Uiso 1 1 calc R . .
C4 C 0.4344(2) 0.26132(7) 1.10044(10) 0.0247(3) Uani 1 1 d . . .
C5 C 0.4024(2) 0.30193(7) 1.03959(10) 0.0269(4) Uani 1 1 d . . .
H5A H 0.3826 0.3396 1.055 0.032 Uiso 1 1 calc R . .
C6 C 0.4001(2) 0.28600(6) 0.95553(10) 0.0266(4) Uani 1 1 d . . .
H6 H 0.3795 0.3133 0.9125 0.032 Uiso 1 1 calc R . .
C7 C 0.4161(2) 0.21613(7) 0.83937(10) 0.0274(4) Uani 1 1 d . . .
N1 N 0.4398(2) 0.27703(6) 1.19073(9) 0.0337(3) Uani 1 1 d . . .
O1 O 0.47903(19) 0.25670(5) 0.79244(8) 0.0396(3) Uani 1 1 d . . .
O2 O 0.35331(19) 0.17299(5) 0.81168(8) 0.0437(3) Uani 1 1 d . . .
H1 H 0.467(4) 0.2472(11) 0.7340(17) 0.093(9) Uiso 1 1 d . . .
O3 O 0.4150(2) 0.32550(5) 1.20873(8) 0.0512(4) Uani 1 1 d . . .
O4 O 0.4704(2) 0.24056(6) 1.24412(8) 0.0550(4) Uani 1 1 d . . .
Cl1 Cl 0.50556(7) 0.122130(16) 0.97490(3) 0.03508(12) Uani 1 1 d . . .
C8 C 0.7292(2) 0.51244(6) 0.16573(9) 0.0205(3) Uani 1 1 d . . .
C9 C 0.7681(2) 0.55070(6) 0.23141(9) 0.0198(3) Uani 1 1 d . . .
C10 C 0.7497(2) 0.53609(6) 0.31550(10) 0.0222(3) Uani 1 1 d . . .
H10 H 0.7795 0.5617 0.3601 0.027 Uiso 1 1 calc R . .
C11 C 0.6869(2) 0.48316(6) 0.33254(9) 0.0222(3) Uani 1 1 d . . .
C12 C 0.6455(2) 0.44407(6) 0.27053(10) 0.0241(3) Uani 1 1 d . . .
H12 H 0.6019 0.408 0.2844 0.029 Uiso 1 1 calc R . .
C13 C 0.6696(2) 0.45914(6) 0.18744(10) 0.0237(3) Uani 1 1 d . . .
H13 H 0.645 0.4325 0.1437 0.028 Uiso 1 1 calc R . .
C14 C 0.7438(2) 0.52613(6) 0.07317(10) 0.0249(4) Uani 1 1 d . . .
N2 N 0.6642(2) 0.46832(6) 0.42168(9) 0.0302(3) Uani 1 1 d . . .
O5 O 0.75431(19) 0.48088(5) 0.02681(8) 0.0361(3) Uani 1 1 d . . .
H5 H 0.761(3) 0.4902(9) -0.0284(15) 0.063(7) Uiso 1 1 d . . .
O6 O 0.7422(2) 0.57256(5) 0.04506(7) 0.0454(3) Uani 1 1 d . . .
O7 O 0.56276(19) 0.42909(5) 0.43708(8) 0.0436(3) Uani 1 1 d . . .
O8 O 0.7498(2) 0.49620(5) 0.47676(8) 0.0466(4) Uani 1 1 d . . .
Cl2 Cl 0.84425(6) 0.617806(15) 0.21428(3) 0.02827(11) Uani 1 1 d . . .
C15 C 0.4346(2) 0.26906(6) 0.56648(10) 0.0236(3) Uani 1 1 d . . .
C16 C 0.4231(2) 0.25824(6) 0.47929(10) 0.0239(3) Uani 1 1 d . . .
C17 C 0.4049(2) 0.20252(7) 0.45681(11) 0.0295(4) Uani 1 1 d . . .
H17 H 0.3977 0.1921 0.3986 0.035 Uiso 1 1 calc R . .
C18 C 0.3971(2) 0.16218(7) 0.51915(11) 0.0316(4) Uani 1 1 d . . .
H18 H 0.3843 0.1241 0.5037 0.038 Uiso 1 1 calc R . .
C19 C 0.4079(2) 0.17718(7) 0.60281(11) 0.0305(4) Uani 1 1 d . . .
H19 H 0.4011 0.1493 0.6451 0.037 Uiso 1 1 calc R . .
N3 N 0.42798(19) 0.23108(5) 0.62666(8) 0.0273(3) Uani 1 1 d . . .
N4 N 0.4239(3) 0.29973(7) 0.42026(10) 0.0388(4) Uani 1 1 d . . .
H4A H 0.459(3) 0.3307(9) 0.4368(14) 0.052(7) Uiso 1 1 d . . .
H4B H 0.436(3) 0.2899(9) 0.3669(17) 0.075(8) Uiso 1 1 d . . .
Cl3 Cl 0.45593(7) 0.337412(17) 0.60068(3) 0.03707(12) Uani 1 1 d . . .
C20 C 0.7465(2) 0.46547(6) -0.19998(10) 0.0207(3) Uani 1 1 d . . .
C21 C 0.7724(2) 0.47574(6) -0.28586(9) 0.0215(3) Uani 1 1 d . . .
C22 C 0.8240(2) 0.52984(7) -0.30568(10) 0.0256(4) Uani 1 1 d . . .
H22 H 0.8425 0.5396 -0.3629 0.031 Uiso 1 1 calc R . .
C23 C 0.8482(2) 0.56915(7) -0.24267(11) 0.0284(4) Uani 1 1 d . . .
H23 H 0.8823 0.6062 -0.2562 0.034 Uiso 1 1 calc R . .
C24 C 0.8225(2) 0.55438(7) -0.15968(10) 0.0272(4) Uani 1 1 d . . .
H24 H 0.8411 0.5815 -0.1162 0.033 Uiso 1 1 calc R . .
N5 N 0.77182(18) 0.50256(5) -0.13882(8) 0.0244(3) Uani 1 1 d . . .
N6 N 0.7496(2) 0.43509(7) -0.34584(10) 0.0375(4) Uani 1 1 d . . .
H6A H 0.715(3) 0.4028(10) -0.3289(14) 0.061(7) Uiso 1 1 d . . .
H6B H 0.755(3) 0.4436(8) -0.3961(14) 0.049(6) Uiso 1 1 d . . .
Cl4 Cl 0.67158(6) 0.399824(16) -0.17057(3) 0.02975(11) 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 1.395(2) . ?
C1 C6 1.397(2) . ?
C1 C7 1.501(2) . ?
C2 C3 1.383(2) . ?
C2 Cl1 1.7302(15) . ?
C3 C4 1.382(2) . ?
C3 H3 0.95 . ?
C4 C5 1.379(2) . ?
C4 N1 1.472(2) . ?
C5 C6 1.379(2) . ?
C5 H5A 0.95 . ?
C6 H6 0.95 . ?
C7 O2 1.2010(19) . ?
C7 O1 1.3189(19) . ?
N1 O3 1.2153(17) . ?
N1 O4 1.2264(18) . ?
O1 H1 0.95(3) . ?
C8 C13 1.399(2) . ?
C8 C9 1.401(2) . ?
C8 C14 1.506(2) . ?
C9 C10 1.386(2) . ?
C9 Cl2 1.7285(15) . ?
C10 C11 1.381(2) . ?
C10 H10 0.95 . ?
C11 C12 1.376(2) . ?
C11 N2 1.469(2) . ?
C12 C13 1.381(2) . ?
C12 H12 0.95 . ?
C13 H13 0.95 . ?
C14 O6 1.2015(18) . ?
C14 O5 1.3161(18) . ?
N2 O7 1.2203(17) . ?
N2 O8 1.2291(18) . ?
O5 H5 0.90(2) . ?
C15 N3 1.320(2) . ?
C15 C16 1.397(2) . ?
C15 Cl3 1.7343(15) . ?
C16 N4 1.365(2) . ?
C16 C17 1.390(2) . ?
C17 C18 1.385(2) . ?
C17 H17 0.95 . ?
C18 C19 1.366(2) . ?
C18 H18 0.95 . ?
C19 N3 1.355(2) . ?
C19 H19 0.95 . ?
N4 H4A 0.82(2) . ?
N4 H4B 0.88(3) . ?
C20 N5 1.3185(19) . ?
C20 C21 1.400(2) . ?
C20 Cl4 1.7380(15) . ?
C21 N6 1.364(2) . ?
C21 C22 1.392(2) . ?
C22 C23 1.375(2) . ?
C22 H22 0.95 . ?
C23 C24 1.379(2) . ?
C23 H23 0.95 . ?
C24 N5 1.344(2) . ?
C24 H24 0.95 . ?
N6 H6A 0.86(2) . ?
N6 H6B 0.82(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
C2 C1 C6 118.38(14) . . ?
C2 C1 C7 122.89(14) . . ?
C6 C1 C7 118.70(14) . . ?
C3 C2 C1 121.09(14) . . ?
C3 C2 Cl1 116.25(12) . . ?
C1 C2 Cl1 122.57(12) . . ?
C4 C3 C2 118.09(14) . . ?
C4 C3 H3 121 . . ?
C2 C3 H3 121 . . ?
C5 C4 C3 123.06(14) . . ?
C5 C4 N1 119.05(14) . . ?
C3 C4 N1 117.88(14) . . ?
C4 C5 C6 117.68(14) . . ?
C4 C5 H5A 121.2 . . ?
C6 C5 H5A 121.2 . . ?
C5 C6 C1 121.69(15) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
O2 C7 O1 124.46(15) . . ?
O2 C7 C1 123.57(15) . . ?
O1 C7 C1 111.95(14) . . ?
O3 N1 O4 123.22(14) . . ?
O3 N1 C4 118.46(14) . . ?
O4 N1 C4 118.32(14) . . ?
C7 O1 H1 110.7(17) . . ?
C13 C8 C9 118.04(13) . . ?
C13 C8 C14 118.49(13) . . ?
C9 C8 C14 123.46(13) . . ?
C10 C9 C8 121.04(13) . . ?
C10 C9 Cl2 115.76(11) . . ?
C8 C9 Cl2 123.20(11) . . ?
C11 C10 C9 118.04(14) . . ?
C11 C10 H10 121 . . ?
C9 C10 H10 121 . . ?
C12 C11 C10 123.33(14) . . ?
C12 C11 N2 118.93(14) . . ?
C10 C11 N2 117.74(14) . . ?
C11 C12 C13 117.53(14) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
C12 C13 C8 121.99(14) . . ?
C12 C13 H13 119 . . ?
C8 C13 H13 119 . . ?
O6 C14 O5 124.28(15) . . ?
O6 C14 C8 124.16(14) . . ?
O5 C14 C8 111.55(13) . . ?
O7 N2 O8 123.63(14) . . ?
O7 N2 C11 118.55(14) . . ?
O8 N2 C11 117.81(14) . . ?
C14 O5 H5 109.8(14) . . ?
N3 C15 C16 125.19(14) . . ?
N3 C15 Cl3 116.01(12) . . ?
C16 C15 Cl3 118.79(12) . . ?
N4 C16 C17 122.33(15) . . ?
N4 C16 C15 122.20(15) . . ?
C17 C16 C15 115.45(14) . . ?
C18 C17 C16 120.08(15) . . ?
C18 C17 H17 120 . . ?
C16 C17 H17 120 . . ?
C19 C18 C17 119.91(15) . . ?
C19 C18 H18 120 . . ?
C17 C18 H18 120 . . ?
N3 C19 C18 121.33(15) . . ?
N3 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C15 N3 C19 118.03(14) . . ?
C16 N4 H4A 117.3(15) . . ?
C16 N4 H4B 117.3(15) . . ?
H4A N4 H4B 120(2) . . ?
N5 C20 C21 124.65(14) . . ?
N5 C20 Cl4 116.74(11) . . ?
C21 C20 Cl4 118.61(12) . . ?
N6 C21 C22 122.43(15) . . ?
N6 C21 C20 121.85(15) . . ?
C22 C21 C20 115.71(14) . . ?
C23 C22 C21 120.22(15) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.42(15) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
N5 C24 C23 121.60(15) . . ?
N5 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C20 N5 C24 118.38(13) . . ?
C21 N6 H6A 117.1(15) . . ?
C21 N6 H6B 118.8(14) . . ?
H6A N6 H6B 124(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(2) . . . . ?
C7 C1 C2 C3 -178.53(15) . . . . ?
C6 C1 C2 Cl1 -176.86(12) . . . . ?
C7 C1 C2 Cl1 4.9(2) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
Cl1 C2 C3 C4 177.72(12) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C2 C3 C4 N1 179.93(14) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
N1 C4 C5 C6 179.32(14) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C7 C1 C6 C5 177.83(15) . . . . ?
C2 C1 C7 O2 33.2(3) . . . . ?
C6 C1 C7 O2 -145.04(18) . . . . ?
C2 C1 C7 O1 -148.23(15) . . . . ?
C6 C1 C7 O1 33.5(2) . . . . ?
C5 C4 N1 O3 0.3(2) . . . . ?
C3 C4 N1 O3 179.55(15) . . . . ?
C5 C4 N1 O4 -179.20(16) . . . . ?
C3 C4 N1 O4 0.0(2) . . . . ?
C13 C8 C9 C10 0.6(2) . . . . ?
C14 C8 C9 C10 179.05(14) . . . . ?
C13 C8 C9 Cl2 179.58(11) . . . . ?
C14 C8 C9 Cl2 -1.9(2) . . . . ?
C8 C9 C10 C11 -1.8(2) . . . . ?
Cl2 C9 C10 C11 179.13(11) . . . . ?
C9 C10 C11 C12 1.4(2) . . . . ?
C9 C10 C11 N2 -178.84(13) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
N2 C11 C12 C13 -179.50(13) . . . . ?
C11 C12 C13 C8 -1.6(2) . . . . ?
C9 C8 C13 C12 1.2(2) . . . . ?
C14 C8 C13 C12 -177.39(14) . . . . ?
C13 C8 C14 O6 158.81(16) . . . . ?
C9 C8 C14 O6 -19.7(2) . . . . ?
C13 C8 C14 O5 -19.8(2) . . . . ?
C9 C8 C14 O5 161.70(14) . . . . ?
C12 C11 N2 O7 -20.2(2) . . . . ?
C10 C11 N2 O7 160.04(15) . . . . ?
C12 C11 N2 O8 159.55(15) . . . . ?
C10 C11 N2 O8 -20.3(2) . . . . ?
N3 C15 C16 N4 177.51(16) . . . . ?
Cl3 C15 C16 N4 -1.5(2) . . . . ?
N3 C15 C16 C17 -0.5(2) . . . . ?
Cl3 C15 C16 C17 -179.54(12) . . . . ?
N4 C16 C17 C18 -177.34(16) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 N3 -0.6(3) . . . . ?
C16 C15 N3 C19 -0.2(2) . . . . ?
Cl3 C15 N3 C19 178.81(12) . . . . ?
C18 C19 N3 C15 0.8(2) . . . . ?
N5 C20 C21 N6 177.94(16) . . . . ?
Cl4 C20 C21 N6 -3.3(2) . . . . ?
N5 C20 C21 C22 -1.7(2) . . . . ?
Cl4 C20 C21 C22 177.11(11) . . . . ?
N6 C21 C22 C23 -178.97(16) . . . . ?
C20 C21 C22 C23 0.7(2) . . . . ?
C21 C22 C23 C24 0.5(2) . . . . ?
C22 C23 C24 N5 -0.9(2) . . . . ?
C21 C20 N5 C24 1.4(2) . . . . ?
Cl4 C20 N5 C24 -177.43(11) . . . . ?
C23 C24 N5 C20 0.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N3 0.95(3) 1.74(3) 2.690(2) 176(2) .
C19 H19 O2 0.95 2.73 3.342(2) 123 .
O5 H5 N5 0.90(2) 1.77(2) 2.674(2) 175(2) .
C24 H24 O6 0.95 2.69 3.342(2) 127 .
N4 H4A O7 0.82(2) 2.48(2) 3.270(2) 162(2) .
N4 H4A Cl3 0.82(2) 2.59(2) 2.983(2) 111(2) .
N4 H4B O4 0.88(3) 2.30(3) 3.157(2) 164(2) 1_554
N4 H4B O3 0.88(3) 2.63(3) 3.391(2) 144(2) 1_554
N6 H6A Cl4 0.86(2) 2.54(2) 2.976(2) 113(2) .
N6 H6A Cl3 0.86(2) 2.62(2) 3.220(2) 128(2) 1_554
N6 H6B O8 0.82(2) 2.37(2) 3.161(2) 162(2) 1_554
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1034739'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_date             2012-11-02T09:10:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 (2-chloro-4-nitrobenzoic acid)(2-amino-5-nitropyridine)
;
_chemical_formula_moiety         'C7 H4 Cl N O4, C5 H5 N3 O2'
_chemical_formula_sum            'C12 H9 Cl N4 O6'
_chemical_formula_weight         340.68
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.7370(3)
_cell_length_b                   12.6714(11)
_cell_length_c                   14.3717(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.984(2)
_cell_angle_gamma                90
_cell_volume                     677.97(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3817
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      28.23

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

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.169
1 0 -1 0.226
0 0 -1 0.04
0 0 1 0.04
0 -1 0 0.172
0 1 0 0.019

_exptl_special_details           
;
  Absorption corrections were made using the program SADABS 
(Sheldrick, 1996)
;

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

_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_T_max  0.9746

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0964
_diffrn_reflns_number            5599
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             3133
_reflns_number_gt                2923
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX3 (Bruker, 2007)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1607P)²+1.5117P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3133
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.1033
_refine_ls_wR_factor_ref         0.2908
_refine_ls_wR_factor_gt          0.2886
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.176
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.29(17)
_refine_diff_density_max         1.762
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.173

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2471(14) 0.2844(5) 0.4734(4) 0.0193(11) Uani 1 1 d . . .
C2 C 0.2122(16) 0.3563(4) 0.3991(4) 0.0203(11) Uani 1 1 d . . .
C3 C 0.0589(17) 0.3270(5) 0.3115(4) 0.0231(12) Uani 1 1 d . . .
H3 H 0.0384 0.3756 0.261 0.028 Uiso 1 1 calc R . .
C4 C -0.0642(16) 0.2232(5) 0.3007(4) 0.0211(11) Uani 1 1 d . . .
C5 C -0.0400(17) 0.1495(5) 0.3732(5) 0.0250(12) Uani 1 1 d . . .
H5 H -0.1321 0.08 0.3644 0.03 Uiso 1 1 calc R . .
C6 C 0.1227(16) 0.1818(5) 0.4576(4) 0.0229(12) Uani 1 1 d . . .
H6 H 0.1517 0.1322 0.5073 0.027 Uiso 1 1 calc R . .
C7 C 0.4172(17) 0.3121(5) 0.5698(4) 0.0250(12) Uani 1 1 d . . .
N1 N -0.2256(17) 0.1916(5) 0.2080(4) 0.0301(12) Uani 1 1 d . . .
O1 O 0.5807(14) 0.2297(4) 0.6085(3) 0.0301(10) Uani 1 1 d . . .
H1 H 0.6557 0.2441 0.6638 0.045 Uiso 1 1 calc R . .
O2 O 0.3954(15) 0.3980(4) 0.6063(4) 0.0360(12) Uani 1 1 d . . .
O3 O -0.4081(17) 0.1117(5) 0.2032(4) 0.0440(14) Uani 1 1 d . . .
O4 O -0.1801(18) 0.2475(5) 0.1423(4) 0.0438(14) Uani 1 1 d . . .
Cl1 Cl 0.3559(4) 0.48618(11) 0.41020(10) 0.0270(4) Uani 1 1 d . . .
C9 C 0.8923(18) 0.3172(5) 0.8398(4) 0.0248(12) Uani 1 1 d . . .
C10 C 1.0275(19) 0.2989(5) 0.9340(5) 0.0270(13) Uani 1 1 d . . .
H10 H 0.999 0.3508 0.9805 0.032 Uiso 1 1 calc R . .
C11 C 1.1976(18) 0.2067(6) 0.9568(4) 0.0271(13) Uani 1 1 d . . .
H11 H 1.2917 0.1931 1.0192 0.032 Uiso 1 1 calc R . .
C12 C 1.2314(16) 0.1320(4) 0.8864(4) 0.0217(12) Uani 1 1 d . . .
C13 C 1.0970(18) 0.1535(5) 0.7952(4) 0.0256(12) Uani 1 1 d . . .
H13 H 1.128 0.1033 0.7475 0.031 Uiso 1 1 calc R . .
N2 N 0.9247(15) 0.2438(5) 0.7736(4) 0.0253(11) Uani 1 1 d . . .
N3 N 0.7270(19) 0.4075(5) 0.8136(5) 0.0345(14) Uani 1 1 d . . .
H3A H 0.67(3) 0.416(9) 0.763(8) 0.04(3) Uiso 1 1 d . . .
H3B H 0.72(3) 0.453(9) 0.854(7) 0.04(3) Uiso 1 1 d . . .
N4 N 1.4177(15) 0.0333(5) 0.9065(4) 0.0286(12) Uani 1 1 d . . .
O5 O 1.4989(17) 0.0112(5) 0.9886(4) 0.0448(14) Uani 1 1 d . . .
O6 O 1.4818(16) -0.0241(5) 0.8410(4) 0.0416(13) 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 C6 1.393(8) . ?
C1 C2 1.400(8) . ?
C1 C7 1.514(8) . ?
C2 C3 1.387(9) . ?
C2 Cl1 1.735(6) . ?
C3 C4 1.397(9) . ?
C3 H3 0.95 . ?
C4 C5 1.397(9) . ?
C4 N1 1.469(7) . ?
C5 C6 1.372(9) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 O2 1.214(9) . ?
C7 O1 1.309(8) . ?
N1 O4 1.203(8) . ?
N1 O3 1.220(8) . ?
O1 H1 0.84 . ?
C9 N3 1.339(9) . ?
C9 N2 1.344(8) . ?
C9 C10 1.423(9) . ?
C10 C11 1.357(10) . ?
C10 H10 0.95 . ?
C11 C12 1.399(9) . ?
C11 H11 0.95 . ?
C12 C13 1.389(9) . ?
C12 N4 1.448(8) . ?
C13 N2 1.336(9) . ?
C13 H13 0.95 . ?
N3 H3A 0.74(11) . ?
N3 H3B 0.82(11) . ?
N4 O5 1.225(8) . ?
N4 O6 1.230(8) . ?

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
C6 C1 C2 118.4(5) . . ?
C6 C1 C7 118.2(5) . . ?
C2 C1 C7 123.4(5) . . ?
C3 C2 C1 121.5(5) . . ?
C3 C2 Cl1 115.9(5) . . ?
C1 C2 Cl1 122.6(5) . . ?
C2 C3 C4 117.3(5) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C5 C4 C3 123.2(6) . . ?
C5 C4 N1 119.2(6) . . ?
C3 C4 N1 117.6(5) . . ?
C6 C5 C4 117.1(6) . . ?
C6 C5 H5 121.5 . . ?
C4 C5 H5 121.5 . . ?
C5 C6 C1 122.6(6) . . ?
C5 C6 H6 118.7 . . ?
C1 C6 H6 118.7 . . ?
O2 C7 O1 125.3(6) . . ?
O2 C7 C1 124.4(6) . . ?
O1 C7 C1 110.3(5) . . ?
O4 N1 O3 124.2(6) . . ?
O4 N1 C4 118.4(6) . . ?
O3 N1 C4 117.4(6) . . ?
C7 O1 H1 109.5 . . ?
N3 C9 N2 117.4(6) . . ?
N3 C9 C10 121.6(6) . . ?
N2 C9 C10 121.0(6) . . ?
C11 C10 C9 119.3(6) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 118.5(5) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C13 C12 C11 120.1(6) . . ?
C13 C12 N4 119.1(6) . . ?
C11 C12 N4 120.8(5) . . ?
N2 C13 C12 121.0(6) . . ?
N2 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 N2 C9 120.0(5) . . ?
C9 N3 H3A 119(8) . . ?
C9 N3 H3B 116(7) . . ?
H3A N3 H3B 124(10) . . ?
O5 N4 O6 123.6(6) . . ?
O5 N4 C12 117.7(6) . . ?
O6 N4 C12 118.7(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
C6 C1 C2 C3 -0.1(8) . . . . ?
C7 C1 C2 C3 179.1(6) . . . . ?
C6 C1 C2 Cl1 179.9(4) . . . . ?
C7 C1 C2 Cl1 -0.9(8) . . . . ?
C1 C2 C3 C4 0.9(9) . . . . ?
Cl1 C2 C3 C4 -179.2(5) . . . . ?
C2 C3 C4 C5 0.2(9) . . . . ?
C2 C3 C4 N1 -179.8(5) . . . . ?
C3 C4 C5 C6 -1.9(9) . . . . ?
N1 C4 C5 C6 178.1(5) . . . . ?
C4 C5 C6 C1 2.6(9) . . . . ?
C2 C1 C6 C5 -1.7(8) . . . . ?
C7 C1 C6 C5 179.0(6) . . . . ?
C6 C1 C7 O2 -146.5(7) . . . . ?
C2 C1 C7 O2 34.3(10) . . . . ?
C6 C1 C7 O1 31.7(8) . . . . ?
C2 C1 C7 O1 -147.5(6) . . . . ?
C5 C4 N1 O4 -165.1(6) . . . . ?
C3 C4 N1 O4 14.8(9) . . . . ?
C5 C4 N1 O3 17.3(9) . . . . ?
C3 C4 N1 O3 -162.8(6) . . . . ?
N3 C9 C10 C11 -179.1(7) . . . . ?
N2 C9 C10 C11 1.3(10) . . . . ?
C9 C10 C11 C12 -0.5(10) . . . . ?
C10 C11 C12 C13 0.9(9) . . . . ?
C10 C11 C12 N4 178.6(6) . . . . ?
C11 C12 C13 N2 -2.0(9) . . . . ?
N4 C12 C13 N2 -179.7(5) . . . . ?
C12 C13 N2 C9 2.7(9) . . . . ?
N3 C9 N2 C13 178.0(6) . . . . ?
C10 C9 N2 C13 -2.4(10) . . . . ?
C13 C12 N4 O5 -172.2(6) . . . . ?
C11 C12 N4 O5 10.1(9) . . . . ?
C13 C12 N4 O6 6.9(9) . . . . ?
C11 C12 N4 O6 -170.8(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N2 0.84 1.8 2.605(7) 161 .
N3 H3A O2 0.74(11) 2.41(11) 3.127(9) 164(11) .
N3 H3B O5 0.82(11) 2.58(11) 3.307(10) 149(9) 2_757
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1034741'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_date             2012-11-02T08:38:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 (2-chloro-4-nitrobenzoate)(2-amino-3-bromopyridinium)
;
_chemical_formula_moiety         'C7 H3 Cl N O4, C5 H6 Br N2'
_chemical_formula_sum            'C12 H9 Br Cl N3 O4'
_chemical_formula_weight         374.58

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4350(2)
_cell_length_b                   10.3354(3)
_cell_length_c                   11.2546(4)
_cell_angle_alpha                98.577(2)
_cell_angle_beta                 105.0740(10)
_cell_angle_gamma                98.022(2)
_cell_volume                     702.11(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8156
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      28.36

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -2 1 0.144
0 1 0 0.053
0 -1 0 0.044
-2 1 1 0.129
2 -1 -1 0.203
1 0 -2 0.196
0 1 -2 0.184
1 -1 2 0.146
0 0 1 0.148
-1 1 -2 0.132

_exptl_special_details           
;
 Numerical integration absorption corrections based on indexed crystal faces
were applied using the XPREP routine (Bruker, 2004)
;

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

_exptl_absorpt_coefficient_mu    3.136
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 2004)'
_exptl_absorpt_correction_T_min  0.3596
_exptl_absorpt_correction_T_max  0.7242

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_number            16110
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             3389
_reflns_number_gt                2950
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX3 (Bruker, 2007)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0389P)²+0.3660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3389
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0709
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.063

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6183(3) 0.71139(17) 0.20034(15) 0.0239(3) Uani 1 1 d . . .
C2 C 0.6652(3) 0.84180(18) 0.26517(17) 0.0267(4) Uani 1 1 d . . .
C3 C 0.8259(3) 0.93669(18) 0.24964(18) 0.0293(4) Uani 1 1 d . . .
H3 H 0.8568 1.0257 0.2949 0.035 Uiso 1 1 calc R . .
C4 C 0.9391(3) 0.89751(18) 0.16630(17) 0.0264(4) Uani 1 1 d . . .
C5 C 0.8958(3) 0.7703(2) 0.09766(18) 0.0303(4) Uani 1 1 d . . .
H5 H 0.9755 0.7462 0.0402 0.036 Uiso 1 1 calc R . .
C6 C 0.7328(3) 0.67781(19) 0.11437(17) 0.0290(4) Uani 1 1 d . . .
H6 H 0.6987 0.5899 0.0663 0.035 Uiso 1 1 calc R . .
C7 C 0.4591(3) 0.60395(17) 0.22618(16) 0.0259(4) Uani 1 1 d . . .
N1 N 1.1120(3) 0.99729(18) 0.15070(17) 0.0346(4) Uani 1 1 d . . .
O1 O 0.5205(2) 0.57150(15) 0.33022(13) 0.0404(4) Uani 1 1 d . . .
O2 O 0.2845(2) 0.55416(14) 0.14195(12) 0.0323(3) Uani 1 1 d . . .
O3 O 1.1406(3) 1.11131(16) 0.20832(18) 0.0493(4) Uani 1 1 d . . .
O4 O 1.2185(3) 0.96137(18) 0.08073(16) 0.0478(4) Uani 1 1 d . . .
Cl1 Cl 0.52379(10) 0.89101(6) 0.37043(6) 0.04732(15) Uani 1 1 d . . .
C8 C 0.0354(3) 0.36877(17) 0.33914(16) 0.0248(3) Uani 1 1 d . . .
C9 C -0.1395(3) 0.29647(18) 0.37164(17) 0.0268(4) Uani 1 1 d . . .
C10 C -0.3384(3) 0.2513(2) 0.2861(2) 0.0339(4) Uani 1 1 d . . .
H10 H -0.4543 0.2038 0.3093 0.041 Uiso 1 1 calc R . .
C11 C -0.3730(3) 0.2748(2) 0.1631(2) 0.0375(5) Uani 1 1 d . . .
H11 H -0.5101 0.2409 0.1017 0.045 Uiso 1 1 calc R . .
C12 C -0.2067(3) 0.34685(19) 0.13399(17) 0.0303(4) Uani 1 1 d . . .
H12 H -0.2281 0.3647 0.0517 0.036 Uiso 1 1 calc R . .
N2 N -0.0100(3) 0.39376(15) 0.22144(14) 0.0259(3) Uani 1 1 d . . .
H2 H 0.083(4) 0.442(3) 0.202(2) 0.046(7) Uiso 1 1 d . . .
N3 N 0.2346(3) 0.41177(18) 0.41611(16) 0.0355(4) Uani 1 1 d . . .
H3A H 0.328(4) 0.459(2) 0.393(2) 0.035(6) Uiso 1 1 d . . .
H3B H 0.268(4) 0.396(2) 0.492(3) 0.043(7) Uiso 1 1 d . . .
Br1 Br -0.08488(3) 0.26143(2) 0.534354(18) 0.04094(9) 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 1.385(3) . ?
C1 C6 1.394(3) . ?
C1 C7 1.517(2) . ?
C2 C3 1.387(2) . ?
C2 Cl1 1.7322(18) . ?
C3 C4 1.378(3) . ?
C3 H3 0.95 . ?
C4 C5 1.373(3) . ?
C4 N1 1.473(2) . ?
C5 C6 1.388(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 O1 1.246(2) . ?
C7 O2 1.251(2) . ?
N1 O4 1.222(2) . ?
N1 O3 1.222(2) . ?
C8 N3 1.319(2) . ?
C8 N2 1.352(2) . ?
C8 C9 1.421(2) . ?
C9 C10 1.357(3) . ?
C9 Br1 1.8727(18) . ?
C10 C11 1.407(3) . ?
C10 H10 0.95 . ?
C11 C12 1.356(3) . ?
C11 H11 0.95 . ?
C12 N2 1.358(2) . ?
C12 H12 0.95 . ?
N2 H2 0.82(3) . ?
N3 H3A 0.84(3) . ?
N3 H3B 0.87(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 C6 118.01(16) . . ?
C2 C1 C7 122.24(16) . . ?
C6 C1 C7 119.62(16) . . ?
C1 C2 C3 121.97(17) . . ?
C1 C2 Cl1 120.30(14) . . ?
C3 C2 Cl1 117.73(14) . . ?
C4 C3 C2 117.77(17) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C5 C4 C3 122.62(17) . . ?
C5 C4 N1 119.33(17) . . ?
C3 C4 N1 118.05(17) . . ?
C4 C5 C6 118.30(17) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C5 C6 C1 121.28(17) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
O1 C7 O2 126.32(16) . . ?
O1 C7 C1 115.44(15) . . ?
O2 C7 C1 118.21(15) . . ?
O4 N1 O3 123.74(17) . . ?
O4 N1 C4 118.12(17) . . ?
O3 N1 C4 118.13(17) . . ?
N3 C8 N2 119.31(17) . . ?
N3 C8 C9 124.09(16) . . ?
N2 C8 C9 116.61(16) . . ?
C10 C9 C8 120.86(17) . . ?
C10 C9 Br1 121.08(14) . . ?
C8 C9 Br1 118.05(13) . . ?
C9 C10 C11 120.00(18) . . ?
C9 C10 H10 120 . . ?
C11 C10 H10 120 . . ?
C12 C11 C10 118.65(18) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 N2 120.60(17) . . ?
C11 C12 H12 119.7 . . ?
N2 C12 H12 119.7 . . ?
C8 N2 C12 123.18(16) . . ?
C8 N2 H2 119.1(19) . . ?
C12 N2 H2 117.6(18) . . ?
C8 N3 H3A 119.4(16) . . ?
C8 N3 H3B 121.1(17) . . ?
H3A N3 H3B 119(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -2.1(3) . . . . ?
C7 C1 C2 C3 173.79(17) . . . . ?
C6 C1 C2 Cl1 178.36(14) . . . . ?
C7 C1 C2 Cl1 -5.7(2) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
Cl1 C2 C3 C4 179.75(14) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C2 C3 C4 N1 -179.14(17) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
N1 C4 C5 C6 179.70(17) . . . . ?
C4 C5 C6 C1 -1.4(3) . . . . ?
C2 C1 C6 C5 2.7(3) . . . . ?
C7 C1 C6 C5 -173.33(17) . . . . ?
C2 C1 C7 O1 -68.1(2) . . . . ?
C6 C1 C7 O1 107.7(2) . . . . ?
C2 C1 C7 O2 113.8(2) . . . . ?
C6 C1 C7 O2 -70.4(2) . . . . ?
C5 C4 N1 O4 -3.3(3) . . . . ?
C3 C4 N1 O4 177.07(18) . . . . ?
C5 C4 N1 O3 176.63(18) . . . . ?
C3 C4 N1 O3 -3.0(3) . . . . ?
N3 C8 C9 C10 -177.7(2) . . . . ?
N2 C8 C9 C10 2.4(3) . . . . ?
N3 C8 C9 Br1 0.6(3) . . . . ?
N2 C8 C9 Br1 -179.27(13) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
Br1 C9 C10 C11 -177.69(16) . . . . ?
C9 C10 C11 C12 -2.3(3) . . . . ?
C10 C11 C12 N2 0.9(3) . . . . ?
N3 C8 N2 C12 176.18(19) . . . . ?
C9 C8 N2 C12 -3.9(3) . . . . ?
C11 C12 N2 C8 2.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.82(3) 1.93(3) 2.754(2) 175(3) .
N3 H3A O1 0.84(3) 1.92(3) 2.757(2) 175(2) .
N3 H3B O1 0.87(3) 2.05(3) 2.846(2) 151(2) 2_666
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1034743'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_date             2012-11-02T13:30:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 (2-chloro-4-nitrobenzoic acid)(2-chloro-3-hydroxypyridine) 
;
_chemical_formula_moiety         'C7 H4 Cl N O4, C5 H4 Cl N O'
_chemical_formula_sum            'C12 H8 Cl2 N2 O5'
_chemical_formula_weight         331.1

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1583(2)
_cell_length_b                   9.9176(2)
_cell_length_c                   11.1477(3)
_cell_angle_alpha                83.332(2)
_cell_angle_beta                 76.2620(10)
_cell_angle_gamma                77.0530(10)
_cell_volume                     643.14(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4342
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      28.23

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.71
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.055
0 0 1 0.094
0 1 -2 0.071
0 -1 2 0.122
2 1 0 0.091
0 -1 -2 0.087
-1 2 0 0.137
1 -2 0 0.16
-1 -1 0 0.08
0 1 1 0.088

_exptl_special_details           
;
 Numerical integration absorption corrections based on indexed crystal faces
were applied using the XPREP routine (Bruker, 2004)
;

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

_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 2004)'
_exptl_absorpt_correction_T_min  0.8896
_exptl_absorpt_correction_T_max  0.9399

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_number            8899
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3089
_reflns_number_gt                2461
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX3 (Bruker, 2007)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0432P)²+0.0434P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3089
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5217(2) 0.49556(13) 0.78574(12) 0.0207(3) Uani 1 1 d . . .
C2 C 0.7013(2) 0.49662(13) 0.84156(12) 0.0214(3) Uani 1 1 d . . .
C3 C 0.7776(2) 0.38515(13) 0.91896(12) 0.0235(3) Uani 1 1 d . . .
H3 H 0.9019 0.3848 0.9558 0.028 Uiso 1 1 calc R . .
C4 C 0.6681(2) 0.27493(13) 0.94084(12) 0.0235(3) Uani 1 1 d . . .
C5 C 0.4892(2) 0.26935(13) 0.88852(12) 0.0250(3) Uani 1 1 d . . .
H5A H 0.4155 0.1925 0.9067 0.03 Uiso 1 1 calc R . .
C6 C 0.4204(2) 0.37982(13) 0.80836(12) 0.0240(3) Uani 1 1 d . . .
H6 H 0.3021 0.3767 0.7681 0.029 Uiso 1 1 calc R . .
C7 C 0.4279(2) 0.61627(13) 0.70430(12) 0.0219(3) Uani 1 1 d . . .
O1 O 0.37258(17) 0.57454(10) 0.61069(9) 0.0285(2) Uani 1 1 d . . .
O2 O 0.40321(18) 0.73544(10) 0.72711(10) 0.0339(3) Uani 1 1 d . . .
O3 O 0.6273(2) 0.07517(10) 1.06597(10) 0.0405(3) Uani 1 1 d . . .
O4 O 0.93890(19) 0.14901(11) 1.04553(10) 0.0405(3) Uani 1 1 d . . .
N1 N 0.7499(2) 0.15794(11) 1.02362(11) 0.0300(3) Uani 1 1 d . . .
Cl1 Cl -0.08522(6) 0.65678(4) 0.42878(3) 0.03338(11) Uani 1 1 d . . .
C8 C 0.0596(2) 0.79162(13) 0.39733(12) 0.0228(3) Uani 1 1 d . . .
C9 C 0.0009(2) 0.89931(14) 0.31134(13) 0.0252(3) Uani 1 1 d . . .
C10 C 0.1162(2) 1.00714(14) 0.29199(13) 0.0296(3) Uani 1 1 d . . .
H10 H 0.0798 1.0836 0.2354 0.036 Uiso 1 1 calc R . .
C11 C 0.2851(3) 1.00278(15) 0.35571(14) 0.0321(3) Uani 1 1 d . . .
H11 H 0.367 1.0756 0.3433 0.039 Uiso 1 1 calc R . .
C12 C 0.3325(3) 0.89051(14) 0.43764(14) 0.0314(3) Uani 1 1 d . . .
H12 H 0.4493 0.8872 0.4809 0.038 Uiso 1 1 calc R . .
N2 N 0.22045(19) 0.78619(11) 0.45856(11) 0.0254(2) Uani 1 1 d . . .
O5 O -0.16349(19) 0.89057(12) 0.25222(11) 0.0384(3) Uani 1 1 d . . .
Cl2 Cl 0.84494(6) 0.63208(3) 0.81417(3) 0.03149(11) Uani 1 1 d . . .
H5 H -0.185(3) 0.958(2) 0.211(2) 0.061(7) Uiso 1 1 d . . .
H1 H 0.323(3) 0.642(2) 0.568(2) 0.061(6) Uiso 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 1.3943(18) . ?
C1 C6 1.3962(18) . ?
C1 C7 1.5093(17) . ?
C2 C3 1.3877(18) . ?
C2 Cl2 1.7289(13) . ?
C3 C4 1.3784(18) . ?
C3 H3 0.95 . ?
C4 C5 1.3771(19) . ?
C4 N1 1.4704(16) . ?
C5 C6 1.3866(18) . ?
C5 H5A 0.95 . ?
C6 H6 0.95 . ?
C7 O2 1.2064(16) . ?
C7 O1 1.3072(16) . ?
O1 H1 0.82(2) . ?
O3 N1 1.2183(16) . ?
O4 N1 1.2274(16) . ?
Cl1 C8 1.7272(13) . ?
C8 N2 1.3188(17) . ?
C8 C9 1.3943(18) . ?
C9 O5 1.3548(17) . ?
C9 C10 1.3815(19) . ?
C10 C11 1.383(2) . ?
C10 H10 0.95 . ?
C11 C12 1.380(2) . ?
C11 H11 0.95 . ?
C12 N2 1.3371(18) . ?
C12 H12 0.95 . ?
O5 H5 0.77(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
C2 C1 C6 118.86(11) . . ?
C2 C1 C7 122.62(11) . . ?
C6 C1 C7 118.50(11) . . ?
C3 C2 C1 120.75(12) . . ?
C3 C2 Cl2 117.02(10) . . ?
C1 C2 Cl2 122.19(10) . . ?
C4 C3 C2 118.13(12) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C5 C4 C3 123.29(12) . . ?
C5 C4 N1 119.19(12) . . ?
C3 C4 N1 117.53(12) . . ?
C4 C5 C6 117.64(12) . . ?
C4 C5 H5A 121.2 . . ?
C6 C5 H5A 121.2 . . ?
C5 C6 C1 121.26(12) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
O2 C7 O1 125.56(12) . . ?
O2 C7 C1 122.82(12) . . ?
O1 C7 C1 111.59(11) . . ?
C7 O1 H1 109.5(15) . . ?
O3 N1 O4 123.76(12) . . ?
O3 N1 C4 118.36(12) . . ?
O4 N1 C4 117.88(12) . . ?
N2 C8 C9 123.77(12) . . ?
N2 C8 Cl1 116.84(10) . . ?
C9 C8 Cl1 119.39(10) . . ?
O5 C9 C10 124.67(12) . . ?
O5 C9 C8 117.93(12) . . ?
C10 C9 C8 117.40(12) . . ?
C9 C10 C11 119.39(13) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 118.69(13) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
N2 C12 C11 122.64(13) . . ?
N2 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C8 N2 C12 118.09(11) . . ?
C9 O5 H5 107.3(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 -0.4(2) . . . . ?
C7 C1 C2 C3 177.94(12) . . . . ?
C6 C1 C2 Cl2 177.32(10) . . . . ?
C7 C1 C2 Cl2 -4.34(18) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
Cl2 C2 C3 C4 -179.08(10) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C2 C3 C4 N1 -179.64(12) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
N1 C4 C5 C6 -178.33(12) . . . . ?
C4 C5 C6 C1 -2.9(2) . . . . ?
C2 C1 C6 C5 2.5(2) . . . . ?
C7 C1 C6 C5 -175.89(12) . . . . ?
C2 C1 C7 O2 -39.7(2) . . . . ?
C6 C1 C7 O2 138.66(14) . . . . ?
C2 C1 C7 O1 142.22(13) . . . . ?
C6 C1 C7 O1 -39.44(16) . . . . ?
C5 C4 N1 O3 -16.58(19) . . . . ?
C3 C4 N1 O3 163.91(12) . . . . ?
C5 C4 N1 O4 163.04(13) . . . . ?
C3 C4 N1 O4 -16.47(18) . . . . ?
N2 C8 C9 O5 178.23(13) . . . . ?
Cl1 C8 C9 O5 -2.43(19) . . . . ?
N2 C8 C9 C10 -1.3(2) . . . . ?
Cl1 C8 C9 C10 177.99(10) . . . . ?
O5 C9 C10 C11 -178.33(14) . . . . ?
C8 C9 C10 C11 1.2(2) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 N2 -0.5(2) . . . . ?
C9 C8 N2 C12 0.5(2) . . . . ?
Cl1 C8 N2 C12 -178.82(10) . . . . ?
C11 C12 N2 C8 0.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O3 0.77(2) 2.27(2) 2.9415(15) 146(2) 1_464
O5 H5 O4 0.77(2) 2.59(2) 3.3074(16) 154(2) 1_464
O1 H1 N2 0.82(2) 1.86(2) 2.6846(14) 175(2) .
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1034745'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_date             2012-11-02T05:50:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 (2-chloro-4-nitrobenzoate)(2-amino-5-bromopyridinium)
;
_chemical_formula_moiety         'C7 H3 Cl N O4, C5 H6 Br N2'
_chemical_formula_sum            'C12 H9 Br Cl N3 O4'
_chemical_formula_weight         374.58

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

_symmetry_space_group_crystal_system Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9305(2)
_cell_length_b                   12.4261(6)
_cell_length_c                   13.8457(7)
_cell_angle_alpha                94.312(2)
_cell_angle_beta                 91.431(2)
_cell_angle_gamma                96.374(2)
_cell_volume                     669.77(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4824
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      28.19

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

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.043
0 -1 0 0.011
-1 0 1 0.284
0 0 -1 0.022
1 0 -1 0.12
0 0 1 0.07

_exptl_special_details           
;
 Numerical integration absorption corrections based on indexed crystal faces
were applied using the XPREP routine (Bruker, 2004)
;

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

_exptl_absorpt_coefficient_mu    3.288
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 2004)'
_exptl_absorpt_correction_T_min  0.2386
_exptl_absorpt_correction_T_max  0.7652

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_number            9646
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3229
_reflns_number_gt                2709
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX3 (Bruker, 2007)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0366P)²+0.1929P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3229
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.029
_refine_ls_wR_factor_ref         0.0689
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      0.907
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.082

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3113(5) 0.28415(16) 0.21076(14) 0.0203(4) Uani 1 1 d . . .
C2 C 0.2766(5) 0.35860(16) 0.14155(14) 0.0212(4) Uani 1 1 d . . .
C3 C 0.0995(5) 0.32779(17) 0.05357(14) 0.0236(4) Uani 1 1 d . . .
H3 H 0.0781 0.3787 0.0065 0.028 Uiso 1 1 calc R . .
C4 C -0.0434(5) 0.22177(17) 0.03674(14) 0.0233(4) Uani 1 1 d . . .
C5 C -0.0135(5) 0.14431(17) 0.10205(15) 0.0257(4) Uani 1 1 d . . .
H5 H -0.1123 0.0713 0.0883 0.031 Uiso 1 1 calc R . .
C6 C 0.1665(5) 0.17740(17) 0.18841(15) 0.0244(4) Uani 1 1 d . . .
H6 H 0.1922 0.1253 0.2341 0.029 Uiso 1 1 calc R . .
C7 C 0.4903(5) 0.31060(17) 0.31020(14) 0.0236(4) Uani 1 1 d . . .
C8 C 0.9082(5) 0.33012(16) 0.57734(14) 0.0201(4) Uani 1 1 d . . .
C9 C 1.0268(5) 0.32301(17) 0.67415(15) 0.0248(4) Uani 1 1 d . . .
H9 H 1.0037 0.3803 0.7222 0.03 Uiso 1 1 calc R . .
C10 C 1.1735(5) 0.23412(17) 0.69790(15) 0.0248(4) Uani 1 1 d . . .
H10 H 1.25 0.2285 0.7628 0.03 Uiso 1 1 calc R . .
C11 C 1.2114(5) 0.15069(16) 0.62632(15) 0.0214(4) Uani 1 1 d . . .
C12 C 1.1043(5) 0.16026(16) 0.53375(14) 0.0222(4) Uani 1 1 d . . .
H12 H 1.1332 0.1046 0.4847 0.027 Uiso 1 1 calc R . .
N1 N -0.2415(5) 0.19061(16) -0.05491(13) 0.0305(4) Uani 1 1 d . . .
N2 N 0.9563(4) 0.24880(13) 0.51107(12) 0.0205(3) Uani 1 1 d . . .
H2 H 0.848(6) 0.253(2) 0.4520(19) 0.036(7) Uiso 1 1 d . . .
N3 N 0.7501(5) 0.41165(15) 0.54975(15) 0.0263(4) Uani 1 1 d . . .
H3A H 0.690(7) 0.409(2) 0.492(2) 0.037(7) Uiso 1 1 d . . .
H3B H 0.713(7) 0.461(2) 0.5904(19) 0.037(8) Uiso 1 1 d . . .
O1 O 0.6194(4) 0.23258(12) 0.34397(10) 0.0296(3) Uani 1 1 d . . .
O2 O 0.4893(5) 0.40274(13) 0.35144(11) 0.0368(4) Uani 1 1 d . . .
O3 O -0.3586(6) 0.09579(16) -0.07178(14) 0.0596(6) Uani 1 1 d . . .
O4 O -0.2842(5) 0.26120(15) -0.10855(12) 0.0464(5) Uani 1 1 d . . .
Cl1 Cl 0.45864(15) 0.49270(4) 0.15697(4) 0.03238(13) Uani 1 1 d . . .
Br1 Br 1.37685(5) 0.020609(17) 0.659135(16) 0.02898(8) 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 C6 1.393(3) . ?
C1 C2 1.396(3) . ?
C1 C7 1.527(3) . ?
C2 C3 1.394(3) . ?
C2 Cl1 1.735(2) . ?
C3 C4 1.374(3) . ?
C3 H3 0.95 . ?
C4 C5 1.382(3) . ?
C4 N1 1.475(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 O2 1.241(3) . ?
C7 O1 1.258(2) . ?
C8 N3 1.321(3) . ?
C8 N2 1.346(3) . ?
C8 C9 1.420(3) . ?
C9 C10 1.359(3) . ?
C9 H9 0.95 . ?
C10 C11 1.402(3) . ?
C10 H10 0.95 . ?
C11 C12 1.357(3) . ?
C11 Br1 1.890(2) . ?
C12 N2 1.354(3) . ?
C12 H12 0.95 . ?
N1 O4 1.214(2) . ?
N1 O3 1.220(3) . ?
N2 H2 0.92(3) . ?
N3 H3A 0.83(3) . ?
N3 H3B 0.82(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
C6 C1 C2 117.68(18) . . ?
C6 C1 C7 117.08(17) . . ?
C2 C1 C7 125.23(18) . . ?
C3 C2 C1 121.28(19) . . ?
C3 C2 Cl1 115.81(15) . . ?
C1 C2 Cl1 122.88(15) . . ?
C4 C3 C2 118.19(18) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 123.02(19) . . ?
C3 C4 N1 117.95(18) . . ?
C5 C4 N1 119.02(19) . . ?
C4 C5 C6 117.3(2) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C5 C6 C1 122.49(19) . . ?
C5 C6 H6 118.8 . . ?
C1 C6 H6 118.8 . . ?
O2 C7 O1 125.94(19) . . ?
O2 C7 C1 119.32(18) . . ?
O1 C7 C1 114.70(18) . . ?
N3 C8 N2 118.69(19) . . ?
N3 C8 C9 123.27(19) . . ?
N2 C8 C9 118.03(18) . . ?
C10 C9 C8 119.83(19) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 119.77(19) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 119.50(19) . . ?
C12 C11 Br1 119.61(16) . . ?
C10 C11 Br1 120.71(15) . . ?
N2 C12 C11 120.22(19) . . ?
N2 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
O4 N1 O3 123.63(19) . . ?
O4 N1 C4 118.13(19) . . ?
O3 N1 C4 118.22(19) . . ?
C8 N2 C12 122.62(17) . . ?
C8 N2 H2 114.0(16) . . ?
C12 N2 H2 122.7(16) . . ?
C8 N3 H3A 116.8(19) . . ?
C8 N3 H3B 119.2(19) . . ?
H3A N3 H3B 124(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
C6 C1 C2 C3 0.8(3) . . . . ?
C7 C1 C2 C3 -178.03(19) . . . . ?
C6 C1 C2 Cl1 -177.17(15) . . . . ?
C7 C1 C2 Cl1 4.0(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
Cl1 C2 C3 C4 178.59(16) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C2 C3 C4 N1 177.74(19) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
N1 C4 C5 C6 -178.26(19) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
C7 C1 C6 C5 177.57(19) . . . . ?
C6 C1 C7 O2 -148.5(2) . . . . ?
C2 C1 C7 O2 30.4(3) . . . . ?
C6 C1 C7 O1 29.5(3) . . . . ?
C2 C1 C7 O1 -151.7(2) . . . . ?
N3 C8 C9 C10 177.0(2) . . . . ?
N2 C8 C9 C10 -2.1(3) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C9 C10 C11 Br1 -174.37(16) . . . . ?
C10 C11 C12 N2 -1.2(3) . . . . ?
Br1 C11 C12 N2 173.94(14) . . . . ?
C3 C4 N1 O4 -3.9(3) . . . . ?
C5 C4 N1 O4 175.2(2) . . . . ?
C3 C4 N1 O3 177.4(2) . . . . ?
C5 C4 N1 O3 -3.5(3) . . . . ?
N3 C8 N2 C12 -177.50(19) . . . . ?
C9 C8 N2 C12 1.7(3) . . . . ?
C11 C12 N2 C8 0.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.92(3) 1.71(3) 2.620(2) 168(2) .
N3 H3A O2 0.83(3) 2.07(3) 2.897(3) 174(3) .
N3 H3B O2 0.82(3) 2.07(3) 2.854(2) 158(3) 2_666
####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1034747'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_date             2012-11-02T08:30:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 (2-chloro-4-nitrobenzoate)(2-amino-5-chloropyridinium)
;
_chemical_formula_moiety         'C7 H3 Cl N O4, C5 H6 Cl N2'
_chemical_formula_sum            'C12 H9 Cl2 N3 O4'
_chemical_formula_weight         330.12

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8601(2)
_cell_length_b                   12.3629(6)
_cell_length_c                   13.9025(7)
_cell_angle_alpha                93.742(2)
_cell_angle_beta                 91.893(2)
_cell_angle_gamma                96.066(2)
_cell_volume                     657.80(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2692
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.4

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

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.802
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.032
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 1 0.355
1 1 -1 0.168
0 -1 0 0.016
0 1 0 0.012
0 0 1 0.025
0 0 -1 0.012

_exptl_special_details           
;
 Numerical integration absorption corrections based on indexed crystal faces
were applied using the XPREP routine (Bruker, 2004)
;

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

_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 2004)'
_exptl_absorpt_correction_T_min  0.8542
_exptl_absorpt_correction_T_max  0.9864

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.1084
_diffrn_reflns_av_unetI/netI     0.0914
_diffrn_reflns_number            7798
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             3158
_reflns_number_gt                2221
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX3 (Bruker, 2007)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0294P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3158
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   0.92
_refine_ls_restrained_S_all      0.92
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.068

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3117(5) 0.28411(16) 0.21251(13) 0.0216(4) Uani 1 1 d . . .
C2 C 0.2761(5) 0.35914(16) 0.14324(13) 0.0230(4) Uani 1 1 d . . .
C3 C 0.1002(5) 0.32879(16) 0.05505(13) 0.0240(4) Uani 1 1 d . . .
H3 H 0.0773 0.3802 0.008 0.029 Uiso 1 1 calc R . .
C4 C -0.0395(5) 0.22202(17) 0.03812(13) 0.0236(4) Uani 1 1 d . . .
C5 C -0.0100(5) 0.14463(17) 0.10342(14) 0.0273(5) Uani 1 1 d . . .
H5 H -0.1089 0.0714 0.0895 0.033 Uiso 1 1 calc R . .
C6 C 0.1679(5) 0.17659(17) 0.18993(13) 0.0258(4) Uani 1 1 d . . .
H6 H 0.1935 0.1238 0.2356 0.031 Uiso 1 1 calc R . .
C7 C 0.4892(5) 0.31060(17) 0.31191(13) 0.0242(4) Uani 1 1 d . . .
N1 N -0.2354(5) 0.19117(16) -0.05458(12) 0.0317(4) Uani 1 1 d . . .
O1 O 0.6270(4) 0.23242(12) 0.34558(9) 0.0310(4) Uani 1 1 d . . .
O2 O 0.4855(4) 0.40286(13) 0.35290(10) 0.0384(4) Uani 1 1 d . . .
O3 O -0.3546(5) 0.09608(15) -0.07120(12) 0.0583(5) Uani 1 1 d . . .
O4 O -0.2772(5) 0.26229(15) -0.10876(11) 0.0489(5) Uani 1 1 d . . .
Cl1 Cl 1.37114(14) 0.02173(5) 0.65463(4) 0.03368(15) Uani 1 1 d . . .
C8 C 0.9126(5) 0.32588(16) 0.57845(13) 0.0219(4) Uani 1 1 d . . .
C9 C 1.0285(5) 0.31503(17) 0.67469(13) 0.0261(4) Uani 1 1 d . . .
H9 H 1.005 0.3714 0.7231 0.031 Uiso 1 1 calc R . .
C10 C 1.1735(5) 0.22412(18) 0.69790(14) 0.0272(4) Uani 1 1 d . . .
H10 H 1.2487 0.2163 0.7626 0.033 Uiso 1 1 calc R . .
C11 C 1.2113(5) 0.14173(17) 0.62548(14) 0.0238(4) Uani 1 1 d . . .
C12 C 1.1055(5) 0.15496(16) 0.53356(14) 0.0243(4) Uani 1 1 d . . .
H12 H 1.1352 0.1003 0.4842 0.029 Uiso 1 1 calc R . .
N2 N 0.9575(4) 0.24548(13) 0.51112(11) 0.0222(4) Uani 1 1 d . . .
H2 H 0.838(6) 0.2490(19) 0.4418(18) 0.049(7) Uiso 1 1 d . . .
N3 N 0.7566(5) 0.40968(15) 0.55124(14) 0.0279(4) Uani 1 1 d . . .
H3A H 0.677(6) 0.4124(19) 0.4883(18) 0.043(7) Uiso 1 1 d . . .
H3B H 0.725(6) 0.459(2) 0.5897(18) 0.041(7) Uiso 1 1 d . . .
Cl2 Cl 0.45659(14) 0.49418(4) 0.15882(4) 0.03372(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 1.393(3) . ?
C1 C6 1.397(3) . ?
C1 C7 1.522(3) . ?
C2 C3 1.392(3) . ?
C2 Cl2 1.737(2) . ?
C3 C4 1.374(3) . ?
C3 H3 0.95 . ?
C4 C5 1.372(3) . ?
C4 N1 1.479(2) . ?
C5 C6 1.378(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 O2 1.243(2) . ?
C7 O1 1.260(2) . ?
N1 O4 1.214(2) . ?
N1 O3 1.221(2) . ?
Cl1 C11 1.733(2) . ?
C8 N3 1.322(3) . ?
C8 N2 1.349(2) . ?
C8 C9 1.416(3) . ?
C9 C10 1.360(3) . ?
C9 H9 0.95 . ?
C10 C11 1.407(3) . ?
C10 H10 0.95 . ?
C11 C12 1.354(3) . ?
C12 N2 1.358(2) . ?
C12 H12 0.95 . ?
N2 H2 1.06(3) . ?
N3 H3A 0.92(2) . ?
N3 H3B 0.80(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
C2 C1 C6 117.64(17) . . ?
C2 C1 C7 125.06(18) . . ?
C6 C1 C7 117.29(18) . . ?
C3 C2 C1 121.41(19) . . ?
C3 C2 Cl2 115.63(16) . . ?
C1 C2 Cl2 122.93(14) . . ?
C4 C3 C2 117.91(19) . . ?
C4 C3 H3 121 . . ?
C2 C3 H3 121 . . ?
C5 C4 C3 123.10(17) . . ?
C5 C4 N1 119.31(19) . . ?
C3 C4 N1 117.58(19) . . ?
C4 C5 C6 117.84(19) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C5 C6 C1 122.08(19) . . ?
C5 C6 H6 119 . . ?
C1 C6 H6 119 . . ?
O2 C7 O1 125.86(17) . . ?
O2 C7 C1 119.86(17) . . ?
O1 C7 C1 114.27(16) . . ?
O4 N1 O3 123.57(18) . . ?
O4 N1 C4 118.26(19) . . ?
O3 N1 C4 118.13(19) . . ?
N3 C8 N2 118.11(18) . . ?
N3 C8 C9 123.52(18) . . ?
N2 C8 C9 118.35(17) . . ?
C10 C9 C8 120.10(17) . . ?
C10 C9 H9 120 . . ?
C8 C9 H9 120 . . ?
C9 C10 C11 119.55(18) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 119.30(19) . . ?
C12 C11 Cl1 120.30(15) . . ?
C10 C11 Cl1 120.32(15) . . ?
C11 C12 N2 120.79(17) . . ?
C11 C12 H12 119.6 . . ?
N2 C12 H12 119.6 . . ?
C8 N2 C12 121.88(17) . . ?
C8 N2 H2 117.5(12) . . ?
C12 N2 H2 120.0(12) . . ?
C8 N3 H3A 120.9(14) . . ?
C8 N3 H3B 120.5(18) . . ?
H3A N3 H3B 119(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.8(3) . . . . ?
C7 C1 C2 C3 -177.96(17) . . . . ?
C6 C1 C2 Cl2 -177.21(14) . . . . ?
C7 C1 C2 Cl2 4.0(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
Cl2 C2 C3 C4 178.31(14) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C2 C3 C4 N1 178.18(16) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
N1 C4 C5 C6 -178.65(17) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
C7 C1 C6 C5 177.54(17) . . . . ?
C2 C1 C7 O2 30.1(3) . . . . ?
C6 C1 C7 O2 -148.6(2) . . . . ?
C2 C1 C7 O1 -150.65(19) . . . . ?
C6 C1 C7 O1 30.6(3) . . . . ?
C5 C4 N1 O4 175.45(18) . . . . ?
C3 C4 N1 O4 -3.5(3) . . . . ?
C5 C4 N1 O3 -2.5(3) . . . . ?
C3 C4 N1 O3 178.55(19) . . . . ?
N3 C8 C9 C10 177.2(2) . . . . ?
N2 C8 C9 C10 -1.5(3) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C9 C10 C11 Cl1 -176.14(15) . . . . ?
C10 C11 C12 N2 -1.4(3) . . . . ?
Cl1 C11 C12 N2 175.43(15) . . . . ?
N3 C8 N2 C12 -177.93(18) . . . . ?
C9 C8 N2 C12 0.9(3) . . . . ?
C11 C12 N2 C8 0.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 1.06(3) 1.53(2) 2.5817(19) 169(2) .
N3 H3A O2 0.92(2) 1.99(2) 2.910(2) 174(2) .
N3 H3B O2 0.80(2) 2.09(2) 2.856(2) 158(2) 2_666
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1034749'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;

_audit_creation_date             2012-11-07T12:48:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 
;
_chemical_formula_sum            'C14 H13 Cl N2 O4'
_chemical_formula_weight         308.71

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.5907(12)
_cell_length_b                   25.242(2)
_cell_length_c                   7.1987(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.654(5)
_cell_angle_gamma                90
_cell_volume                     2784.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2290
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      27.79

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.124
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.016
0 1 0 0.062
1 1 1 0.14
0 1 2 0.179
-1 -1 0 0.078
2 -1 0 0.086
0 2 -1 0.199
1 -1 -1 0.161
-2 -2 -1 0.148

_exptl_special_details           
;
 Numerical integration absorption corrections based on indexed crystal faces
were applied using the XPREP routine (Bruker, 2004)
;

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

_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 2004)'
_exptl_absorpt_correction_T_min  0.9157
_exptl_absorpt_correction_T_max  0.9794

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_number            8530
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             3366
_reflns_number_gt                2395
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX3 (Bruker, 2007)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0499P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3366
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.75434(9) 0.56848(6) 0.6387(2) 0.0233(3) Uani 1 1 d . . .
C2 C 0.71287(10) 0.52028(6) 0.6560(2) 0.0245(3) Uani 1 1 d . . .
C3 C 0.75580(10) 0.47260(6) 0.6528(2) 0.0259(4) Uani 1 1 d . . .
H3 H 0.7276 0.44 0.6689 0.031 Uiso 1 1 calc R . .
C4 C 0.84119(10) 0.47376(6) 0.6255(2) 0.0262(4) Uani 1 1 d . . .
C5 C 0.88493(10) 0.52020(6) 0.6069(2) 0.0277(4) Uani 1 1 d . . .
H5 H 0.9436 0.5198 0.5878 0.033 Uiso 1 1 calc R . .
C6 C 0.84128(10) 0.56750(6) 0.6168(2) 0.0268(4) Uani 1 1 d . . .
H6 H 0.8711 0.6 0.6085 0.032 Uiso 1 1 calc R . .
C7 C 0.70884(10) 0.62144(6) 0.6442(2) 0.0273(4) Uani 1 1 d . . .
N1 N 0.88685(9) 0.42330(6) 0.6190(2) 0.0322(3) Uani 1 1 d . . .
O1 O 0.65026(8) 0.63102(5) 0.50296(19) 0.0424(3) Uani 1 1 d . . .
O2 O 0.73338(8) 0.65032(5) 0.7798(2) 0.0465(4) Uani 1 1 d . . .
O3 O 0.85689(8) 0.38403(5) 0.6823(2) 0.0426(3) Uani 1 1 d . . .
O4 O 0.95374(8) 0.42323(5) 0.5511(2) 0.0433(4) Uani 1 1 d . . .
Cl1 Cl 0.60537(3) 0.519010(17) 0.68724(7) 0.03515(14) Uani 1 1 d . . .
C8 C 0.44953(11) 0.68385(7) 0.4727(2) 0.0304(4) Uani 1 1 d . . .
C9 C 0.38137(11) 0.71949(8) 0.4521(3) 0.0382(4) Uani 1 1 d . . .
H9 H 0.3228 0.7072 0.429 0.046 Uiso 1 1 calc R . .
C10 C 0.39872(12) 0.77284(8) 0.4653(3) 0.0405(5) Uani 1 1 d . . .
H10 H 0.3521 0.7976 0.4489 0.049 Uiso 1 1 calc R . .
C11 C 0.48387(12) 0.79044(7) 0.5021(3) 0.0374(4) Uani 1 1 d . . .
H11 H 0.4959 0.8273 0.5141 0.045 Uiso 1 1 calc R . .
C12 C 0.55141(11) 0.75456(6) 0.5215(2) 0.0286(4) Uani 1 1 d . . .
C13 C 0.43719(12) 0.62532(7) 0.4602(3) 0.0427(5) Uani 1 1 d . . .
H13A H 0.415 0.6153 0.3286 0.064 Uiso 1 1 calc R . .
H13B H 0.3953 0.6145 0.5389 0.064 Uiso 1 1 calc R . .
H13C H 0.4932 0.6077 0.5048 0.064 Uiso 1 1 calc R . .
C14 C 0.64582(11) 0.76943(7) 0.5585(3) 0.0376(4) Uani 1 1 d . . .
H14A H 0.6802 0.7409 0.6283 0.056 Uiso 1 1 calc R . .
H14B H 0.654 0.8021 0.6334 0.056 Uiso 1 1 calc R . .
H14C H 0.6652 0.7751 0.438 0.056 Uiso 1 1 calc R . .
N2 N 0.53189(9) 0.70245(5) 0.50518(19) 0.0267(3) Uani 1 1 d . . .
H2 H 0.5794(13) 0.6768(8) 0.513(3) 0.050(6) Uiso 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 C6 1.393(2) . ?
C1 C2 1.394(2) . ?
C1 C7 1.517(2) . ?
C2 C3 1.379(2) . ?
C2 Cl1 1.7320(16) . ?
C3 C4 1.382(2) . ?
C3 H3 0.95 . ?
C4 C5 1.375(2) . ?
C4 N1 1.464(2) . ?
C5 C6 1.383(2) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 O2 1.222(2) . ?
C7 O1 1.258(2) . ?
N1 O3 1.2196(18) . ?
N1 O4 1.2310(19) . ?
C8 N2 1.346(2) . ?
C8 C9 1.379(2) . ?
C8 C13 1.490(2) . ?
C9 C10 1.373(3) . ?
C9 H9 0.95 . ?
C10 C11 1.378(3) . ?
C10 H10 0.95 . ?
C11 C12 1.376(2) . ?
C11 H11 0.95 . ?
C12 N2 1.350(2) . ?
C12 C14 1.495(2) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
N2 H2 0.98(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
C6 C1 C2 118.12(14) . . ?
C6 C1 C7 119.21(13) . . ?
C2 C1 C7 122.67(14) . . ?
C3 C2 C1 121.70(15) . . ?
C3 C2 Cl1 118.05(12) . . ?
C1 C2 Cl1 120.23(12) . . ?
C2 C3 C4 117.86(15) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C5 C4 C3 122.70(14) . . ?
C5 C4 N1 119.06(15) . . ?
C3 C4 N1 118.24(14) . . ?
C4 C5 C6 118.25(15) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C5 C6 C1 121.32(15) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O2 C7 O1 127.17(16) . . ?
O2 C7 C1 117.88(15) . . ?
O1 C7 C1 114.92(14) . . ?
O3 N1 O4 123.94(14) . . ?
O3 N1 C4 118.25(14) . . ?
O4 N1 C4 117.81(14) . . ?
N2 C8 C9 118.83(16) . . ?
N2 C8 C13 117.67(15) . . ?
C9 C8 C13 123.50(16) . . ?
C10 C9 C8 119.61(17) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 119.99(16) . . ?
C9 C10 H10 120 . . ?
C11 C10 H10 120 . . ?
C12 C11 C10 119.94(17) . . ?
C12 C11 H11 120 . . ?
C10 C11 H11 120 . . ?
N2 C12 C11 118.44(16) . . ?
N2 C12 C14 117.32(14) . . ?
C11 C12 C14 124.23(15) . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 N2 C12 123.17(14) . . ?
C8 N2 H2 117.9(11) . . ?
C12 N2 H2 118.9(11) . . ?

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 0.3(2) . . . . ?
C7 C1 C2 C3 -179.24(15) . . . . ?
C6 C1 C2 Cl1 179.01(12) . . . . ?
C7 C1 C2 Cl1 -0.6(2) . . . . ?
C1 C2 C3 C4 -2.1(2) . . . . ?
Cl1 C2 C3 C4 179.20(12) . . . . ?
C2 C3 C4 C5 1.8(3) . . . . ?
C2 C3 C4 N1 -179.09(14) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
N1 C4 C5 C6 -178.84(14) . . . . ?
C4 C5 C6 C1 -2.1(3) . . . . ?
C2 C1 C6 C5 1.8(2) . . . . ?
C7 C1 C6 C5 -178.58(15) . . . . ?
C6 C1 C7 O2 -67.6(2) . . . . ?
C2 C1 C7 O2 112.02(19) . . . . ?
C6 C1 C7 O1 110.88(18) . . . . ?
C2 C1 C7 O1 -69.5(2) . . . . ?
C5 C4 N1 O3 161.57(16) . . . . ?
C3 C4 N1 O3 -17.5(2) . . . . ?
C5 C4 N1 O4 -17.9(2) . . . . ?
C3 C4 N1 O4 163.01(15) . . . . ?
N2 C8 C9 C10 -0.1(3) . . . . ?
C13 C8 C9 C10 -179.81(18) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C12 1.4(3) . . . . ?
C10 C11 C12 N2 -0.5(3) . . . . ?
C10 C11 C12 C14 179.01(18) . . . . ?
C9 C8 N2 C12 1.0(3) . . . . ?
C13 C8 N2 C12 -179.23(16) . . . . ?
C11 C12 N2 C8 -0.7(3) . . . . ?
C14 C12 N2 C8 179.72(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.98(2) 1.61(2) 2.5822(17) 173(2) .
