# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_4Br2MA_35DNBA_22
_database_code_depnum_ccdc_archive 'CCDC 1556544'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-bromo-2-methylanilinium 3,5-dinitrobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7N1Br1H9 1+, C7N2O6H3 1-'
_chemical_formula_sum            'C14 H12 Br N3 O6'
_chemical_formula_weight         398.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.4081(4)
_cell_length_b                   5.8338(2)
_cell_length_c                   13.2672(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.035(4)
_cell_angle_gamma                90
_cell_volume                     770.23(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.2(3)
_cell_measurement_reflns_used    3371
_cell_measurement_theta_min      3.8350
_cell_measurement_theta_max      28.1620

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    2.706
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150.2(3)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7649
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.949
_diffrn_reflns_theta_max         29.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3622
_reflns_number_gt                3192
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_max     0.755
_reflns_Friedel_fraction_full    0.976

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogen atoms were refined anisotropically. Aromatic 
hydrogen atoms were placed in calculated positions and 
refined as riding on the atoms to which they were bonded. The 
hydrogen atoms of the NH3+ group were identified using Fourier 
difference maps, and the positions and isotropic displacement 
parameters allowed to freely refine. The methyl group H-atoms 
were located initially using Fourier difference maps and the bond 
distances and angles constrained to take standard values; the Uiso 
of the H-atoms was constrained to 1.5Ueq of the C-atom to which 
they are bonded. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0175P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1096 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3622
_refine_ls_number_parameters     230
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0613
_refine_ls_wR_factor_gt          0.0565
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.21146(4) 0.76590(9) 0.80023(3) 0.03070(12) Uani 1 1 d . . . . .
C1 C 0.2115(4) 1.0926(6) 0.9076(3) 0.0171(9) Uani 1 1 d . . . . .
C2 C 0.1888(4) 0.8967(6) 0.9591(3) 0.0182(8) Uani 1 1 d . . . . .
C3 C 0.0602(4) 0.8033(8) 0.9270(3) 0.0215(10) Uani 1 1 d . . . . .
H3 H 0.0412 0.6710 0.9590 0.026 Uiso 1 1 calc R U . . .
C4 C -0.0394(4) 0.9064(7) 0.8477(3) 0.0209(9) Uani 1 1 d . . . . .
C5 C -0.0173(4) 1.1056(7) 0.8012(3) 0.0257(10) Uani 1 1 d . . . . .
H5 H -0.0871 1.1775 0.7509 0.031 Uiso 1 1 calc R U . . .
C6 C 0.1109(4) 1.1989(7) 0.8302(3) 0.0245(10) Uani 1 1 d . . . . .
H6 H 0.1288 1.3315 0.7979 0.029 Uiso 1 1 calc R U . . .
C7 C 0.2982(4) 0.7815(10) 1.0442(3) 0.0282(9) Uani 1 1 d . . . . .
H7A H 0.3565 0.6989 1.0128 0.042 Uiso 1 1 calc R U . . .
H7B H 0.2588 0.6769 1.0825 0.042 Uiso 1 1 calc R U . . .
H7C H 0.3492 0.8953 1.0915 0.042 Uiso 1 1 calc R U . . .
N1 N 0.3485(4) 1.1826(7) 0.9309(3) 0.0186(8) Uani 1 1 d . . . . .
C8 C 0.4023(4) 0.7253(7) 0.7976(3) 0.0192(10) Uani 1 1 d . . . . .
O1 O 0.4845(3) 0.8173(4) 0.8771(2) 0.0219(7) Uani 1 1 d . . . . .
O2 O 0.3555(3) 0.5273(5) 0.7934(2) 0.0267(7) Uani 1 1 d . . . . .
C9 C 0.3570(4) 0.8709(6) 0.6989(3) 0.0157(8) Uani 1 1 d . . . . .
C10 C 0.2439(4) 0.8098(7) 0.6177(3) 0.0194(10) Uani 1 1 d . . . . .
H10 H 0.1949 0.6791 0.6225 0.023 Uiso 1 1 calc R U . . .
C11 C 0.2062(4) 0.9490(6) 0.5294(3) 0.0178(9) Uani 1 1 d . . . . .
C12 C 0.2744(4) 1.1427(6) 0.5171(3) 0.0191(9) Uani 1 1 d . . . . .
H12 H 0.2463 1.2334 0.4570 0.023 Uiso 1 1 calc R U . . .
C13 C 0.3877(4) 1.1959(6) 0.5992(3) 0.0176(9) Uani 1 1 d . . . . .
C14 C 0.4299(4) 1.0633(6) 0.6889(3) 0.0180(9) Uani 1 1 d . . . . .
H14 H 0.5068 1.1030 0.7423 0.022 Uiso 1 1 calc R U . . .
N2 N 0.0869(4) 0.8852(7) 0.4425(3) 0.0265(9) Uani 1 1 d . . . . .
O3 O 0.0381(4) 0.6959(7) 0.4451(3) 0.0468(12) Uani 1 1 d . . . . .
O4 O 0.0444(3) 1.0238(5) 0.3708(2) 0.0334(8) Uani 1 1 d . . . . .
N3 N 0.4647(4) 1.3995(6) 0.5883(3) 0.0238(8) Uani 1 1 d . . . . .
O5 O 0.4179(3) 1.5254(5) 0.5129(2) 0.0307(7) Uani 1 1 d . . . . .
O6 O 0.5724(3) 1.4331(5) 0.6556(2) 0.0379(8) Uani 1 1 d . . . . .
H1B H 0.352(5) 1.298(10) 0.896(4) 0.039(16) Uiso 1 1 d . . . . .
H1A H 0.406(5) 1.070(8) 0.912(4) 0.051(16) Uiso 1 1 d . . . . .
H1C H 0.388(5) 1.219(10) 0.999(4) 0.058(16) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.901(4) . ?
C1 C6 1.381(5) . ?
C1 C2 1.387(5) . ?
C1 N1 1.464(5) . ?
C2 C3 1.392(5) . ?
C2 C7 1.507(5) . ?
C3 C4 1.380(5) . ?
C4 C5 1.366(6) . ?
C5 C6 1.387(6) . ?
C8 O2 1.249(5) . ?
C8 O1 1.267(4) . ?
C8 C9 1.515(5) . ?
C9 C14 1.383(5) . ?
C9 C10 1.390(5) . ?
C10 C11 1.384(5) . ?
C11 C12 1.370(5) . ?
C11 N2 1.474(5) . ?
C12 C13 1.386(5) . ?
C13 C14 1.379(5) . ?
C13 N3 1.464(5) . ?
N2 O3 1.220(5) . ?
N2 O4 1.228(5) . ?
N3 O5 1.221(4) . ?
N3 O6 1.227(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.3(4) . . ?
C6 C1 N1 118.4(4) . . ?
C2 C1 N1 119.2(3) . . ?
C1 C2 C3 117.4(3) . . ?
C1 C2 C7 122.4(4) . . ?
C3 C2 C7 120.2(4) . . ?
C4 C3 C2 120.2(4) . . ?
C5 C4 C3 121.8(4) . . ?
C5 C4 Br1 119.0(3) . . ?
C3 C4 Br1 119.3(3) . . ?
C4 C5 C6 119.0(4) . . ?
C1 C6 C5 119.3(4) . . ?
O2 C8 O1 126.0(4) . . ?
O2 C8 C9 117.5(3) . . ?
O1 C8 C9 116.5(4) . . ?
C14 C9 C10 119.9(3) . . ?
C14 C9 C8 119.8(3) . . ?
C10 C9 C8 120.3(3) . . ?
C11 C10 C9 118.1(4) . . ?
C12 C11 C10 123.8(3) . . ?
C12 C11 N2 117.5(3) . . ?
C10 C11 N2 118.6(4) . . ?
C11 C12 C13 116.2(3) . . ?
C14 C13 C12 122.4(4) . . ?
C14 C13 N3 119.7(3) . . ?
C12 C13 N3 117.9(3) . . ?
C13 C14 C9 119.6(3) . . ?
O3 N2 O4 124.0(4) . . ?
O3 N2 C11 117.9(4) . . ?
O4 N2 C11 118.0(4) . . ?
O5 N3 O6 124.1(4) . . ?
O5 N3 C13 118.1(3) . . ?
O6 N3 C13 117.9(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
C6 H6 O2 0.93 2.64 3.335(5) 132.3 1_565
N1 H1B O2 0.83(6) 1.92(6) 2.731(5) 169(4) 1_565
N1 H1A O1 0.97(5) 1.81(5) 2.766(5) 167(4) .
N1 H1C O1 0.91(5) 1.87(5) 2.744(4) 161(5) 2_657

_refine_diff_density_max         0.405
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.078


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_4Cl2MA_35DNBA_24
_database_code_depnum_ccdc_archive 'CCDC 1556548'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'4-chloro-2-methylanilinium 3,5-dinitrobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7N1Cl1H9 1+, C7N2O6H3 1-'
_chemical_formula_sum            'C14 H12 Cl N3 O6'
_chemical_formula_weight         353.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.2583(6)
_cell_length_b                   5.8537(3)
_cell_length_c                   13.2818(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.933(7)
_cell_angle_gamma                90
_cell_volume                     762.98(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    2233
_cell_measurement_theta_min      3.8150
_cell_measurement_theta_max      26.9500

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.288
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98549
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5839
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.969
_diffrn_reflns_theta_max         27.461
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.914
_reflns_number_total             3155
_reflns_number_gt                2630
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.643
_reflns_Friedel_fraction_max     0.784
_reflns_Friedel_fraction_full    0.809

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogen atoms were refined anisotropically. Aromatic 
hydrogen atoms were placed in calculated positions and 
refined as riding on the atoms to which they were bonded. The hydrogen 
atoms of the NH3+ group were identified using Fourier difference maps,
and the positions and isotropic displacement parameters allowed to freely 
refine. The methyl group H-atoms were located initially using Fourier 
difference maps and the bond distances and angles constrained to take 
standard values; the Uiso of the H-atoms was constrained to 1.5Ueq of the 
C-atom to which they are bonded.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0257P)²+0.0244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 821 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3155
_refine_ls_number_parameters     230
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.0785
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.29139(8) 0.66594(18) 0.30588(8) 0.0374(3) Uani 1 1 d . . . . .
N1 N 0.8458(3) 1.0743(5) 0.4301(3) 0.0197(6) Uani 1 1 d . . . . .
H1A H 0.902(4) 0.964(7) 0.408(3) 0.040(11) Uiso 1 1 d . . . . .
H1B H 0.846(4) 1.199(8) 0.389(4) 0.057(14) Uiso 1 1 d . . . . .
H1C H 0.892(4) 1.116(7) 0.502(3) 0.048(12) Uiso 1 1 d . . . . .
C1 C 0.7065(3) 0.9832(5) 0.4063(3) 0.0194(7) Uani 1 1 d . . . . .
C2 C 0.6837(3) 0.7880(6) 0.4589(3) 0.0211(7) Uani 1 1 d . . . . .
C3 C 0.5525(3) 0.6929(7) 0.4268(3) 0.0239(8) Uani 1 1 d . . . . .
H3 H 0.5335 0.5614 0.4591 0.029 Uiso 1 1 calc R U . . .
C4 C 0.4515(3) 0.7946(6) 0.3470(3) 0.0237(8) Uani 1 1 d . . . . .
C5 C 0.4740(3) 0.9912(6) 0.2983(3) 0.0275(8) Uani 1 1 d . . . . .
H5 H 0.4037 1.0603 0.2468 0.033 Uiso 1 1 calc R U . . .
C6 C 0.6049(3) 1.0853(6) 0.3278(3) 0.0254(8) Uani 1 1 d . . . . .
H6 H 0.6232 1.2162 0.2947 0.031 Uiso 1 1 calc R U . . .
C7 C 0.7938(3) 0.6784(7) 0.5458(3) 0.0299(8) Uani 1 1 d . . . . .
H7A H 0.8584 0.6054 0.5167 0.045 Uiso 1 1 calc R U . . .
H7B H 0.7540 0.5666 0.5809 0.045 Uiso 1 1 calc R U . . .
H7C H 0.8391 0.7930 0.5953 0.045 Uiso 1 1 calc R U . . .
C8 C -0.0976(3) 0.6153(6) 0.2982(3) 0.0202(7) Uani 1 1 d . . . . .
C9 C -0.1408(3) 0.7633(5) 0.2003(3) 0.0181(7) Uani 1 1 d . . . . .
C10 C -0.2554(3) 0.7056(6) 0.1181(3) 0.0198(7) Uani 1 1 d . . . . .
H10 H -0.3062 0.5762 0.1222 0.024 Uiso 1 1 calc R U . . .
C11 C -0.2918(3) 0.8441(6) 0.0306(3) 0.0203(7) Uani 1 1 d . . . . .
C12 C -0.2212(3) 1.0380(6) 0.0196(3) 0.0203(7) Uani 1 1 d . . . . .
H12 H -0.2485 1.1297 -0.0401 0.024 Uiso 1 1 calc R U . . .
C13 C -0.1074(3) 1.0886(5) 0.1022(3) 0.0192(7) Uani 1 1 d . . . . .
C14 C -0.0659(3) 0.9556(5) 0.1916(3) 0.0201(7) Uani 1 1 d . . . . .
H14 H 0.0116 0.9946 0.2455 0.024 Uiso 1 1 calc R U . . .
O1 O -0.0156(2) 0.7070(4) 0.37853(18) 0.0230(5) Uani 1 1 d . . . . .
O2 O -0.1451(2) 0.4187(4) 0.29294(19) 0.0286(6) Uani 1 1 d . . . . .
N2 N -0.4119(3) 0.7835(6) -0.0579(2) 0.0283(7) Uani 1 1 d . . . . .
O3 O -0.4647(3) 0.5981(6) -0.0549(2) 0.0517(9) Uani 1 1 d . . . . .
O4 O -0.4509(2) 0.9204(5) -0.13039(19) 0.0380(7) Uani 1 1 d . . . . .
N3 N -0.0272(3) 1.2914(5) 0.0928(2) 0.0280(7) Uani 1 1 d . . . . .
O5 O -0.0756(2) 1.4229(4) 0.0198(2) 0.0351(6) Uani 1 1 d . . . . .
O6 O 0.0831(3) 1.3197(5) 0.1590(2) 0.0428(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.744(3) . ?
N1 C1 1.470(4) . ?
C1 C6 1.377(4) . ?
C1 C2 1.395(5) . ?
C2 C3 1.403(4) . ?
C2 C7 1.503(5) . ?
C3 C4 1.382(5) . ?
C4 C5 1.372(5) . ?
C5 C6 1.397(4) . ?
C8 O2 1.244(4) . ?
C8 O1 1.269(4) . ?
C8 C9 1.517(4) . ?
C9 C14 1.387(4) . ?
C9 C10 1.393(4) . ?
C10 C11 1.376(4) . ?
C11 C12 1.377(4) . ?
C11 N2 1.477(4) . ?
C12 C13 1.381(4) . ?
C13 C14 1.379(4) . ?
C13 N3 1.471(4) . ?
N2 O3 1.219(4) . ?
N2 O4 1.227(4) . ?
N3 O5 1.224(4) . ?
N3 O6 1.225(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.3(3) . . ?
C6 C1 N1 118.7(3) . . ?
C2 C1 N1 118.9(3) . . ?
C1 C2 C3 117.3(3) . . ?
C1 C2 C7 122.4(3) . . ?
C3 C2 C7 120.3(3) . . ?
C4 C3 C2 120.1(3) . . ?
C5 C4 C3 122.1(3) . . ?
C5 C4 Cl1 119.1(3) . . ?
C3 C4 Cl1 118.8(3) . . ?
C4 C5 C6 118.5(3) . . ?
C1 C6 C5 119.7(3) . . ?
O2 C8 O1 126.2(3) . . ?
O2 C8 C9 117.9(3) . . ?
O1 C8 C9 115.8(3) . . ?
C14 C9 C10 119.5(3) . . ?
C14 C9 C8 120.3(3) . . ?
C10 C9 C8 120.2(3) . . ?
C11 C10 C9 118.6(3) . . ?
C10 C11 C12 123.6(3) . . ?
C10 C11 N2 119.2(3) . . ?
C12 C11 N2 117.1(3) . . ?
C11 C12 C13 116.2(3) . . ?
C14 C13 C12 122.7(3) . . ?
C14 C13 N3 119.2(3) . . ?
C12 C13 N3 118.0(3) . . ?
C13 C14 C9 119.4(3) . . ?
O3 N2 O4 124.1(3) . . ?
O3 N2 C11 117.6(3) . . ?
O4 N2 C11 118.3(3) . . ?
O5 N3 O6 124.1(3) . . ?
O5 N3 C13 117.8(3) . . ?
O6 N3 C13 118.1(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
N1 H1A O1 0.97(4) 1.82(4) 2.771(4) 166(3) 1_655
N1 H1B O2 0.91(5) 1.83(5) 2.737(4) 171(4) 1_665
N1 H1C O1 0.96(4) 1.80(4) 2.742(4) 165(3) 2_656
C6 H6 O4 0.93 2.66 3.288(4) 125.5 2

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_4IA_35DNBA_16
_database_code_depnum_ccdc_archive 'CCDC 1556545'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-iodoaniline 3,5-dinitrobenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6N1I1H6, C7N2O6H4'
_chemical_formula_sum            'C13 H10 I N3 O6'
_chemical_formula_weight         431.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2766(3)
_cell_length_b                   7.3862(3)
_cell_length_c                   14.2883(5)
_cell_angle_alpha                99.348(3)
_cell_angle_beta                 103.715(4)
_cell_angle_gamma                90.271(3)
_cell_volume                     735.39(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    4413
_cell_measurement_theta_min      3.5490
_cell_measurement_theta_max      28.7910

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    2.214
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84943
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10639
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.798
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3391
_reflns_number_gt                2740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogen atoms were refined anisotropically. Aromatic hydrogen 
atoms were placed in calculated positions and 
refined as riding on the atoms to which they were bonded. The 
hydrogen atoms of the NH2 group were identified using Fourier 
difference maps; the positions were allowed to freely refine, but 
the Uiso of the H-atoms was constrained to 1.5Ueq of the N-atom 
to which they are bonded. The hydrogen atom of the carboxylic 
acid group was located using Fourier difference maps and the 
position refined using a distance restraint (0.9 A); the 
Uiso of the H-atom was constrained to 1.5Ueq of the O-atom to 
which it is bonded.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+0.8439P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3391
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      6.278
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.39186(5) 0.19717(5) 0.12800(3) 0.03712(14) Uani 1 1 d . . . . .
N1 N -0.5218(8) -0.3666(8) 0.3918(4) 0.0513(14) Uani 1 1 d . . . . .
H1B H -0.476(11) -0.337(11) 0.450(6) 0.077 Uiso 1 1 d . U . . .
H1A H -0.573(11) -0.473(11) 0.365(6) 0.077 Uiso 1 1 d . U . . .
C1 C -0.4918(7) -0.2451(7) 0.3322(4) 0.0312(11) Uani 1 1 d . . . . .
C2 C -0.4117(7) -0.0715(7) 0.3728(4) 0.0345(12) Uani 1 1 d . . . . .
H2 H -0.3763 -0.0388 0.4405 0.041 Uiso 1 1 calc R U . . .
C3 C -0.3830(7) 0.0536(7) 0.3160(4) 0.0313(11) Uani 1 1 d . . . . .
H3 H -0.3289 0.1696 0.3449 0.038 Uiso 1 1 calc R U . . .
C4 C -0.4353(7) 0.0060(6) 0.2152(4) 0.0280(10) Uani 1 1 d . . . . .
C5 C -0.5155(7) -0.1676(7) 0.1729(4) 0.0312(11) Uani 1 1 d . . . . .
H5 H -0.5528 -0.2004 0.1053 0.037 Uiso 1 1 calc R U . . .
C6 C -0.5392(7) -0.2901(7) 0.2320(4) 0.0344(12) Uani 1 1 d . . . . .
H6 H -0.5889 -0.4078 0.2033 0.041 Uiso 1 1 calc DR U . . .
C7 C -0.0067(7) -0.3612(7) 0.3989(3) 0.0269(10) Uani 1 1 d . . . . .
C8 C 0.0052(6) -0.2515(6) 0.3213(3) 0.0236(9) Uani 1 1 d . . . . .
C9 C -0.0598(6) -0.3284(6) 0.2230(3) 0.0253(10) Uani 1 1 d . . . . .
H9 H -0.1148 -0.4467 0.2048 0.030 Uiso 1 1 calc R U . . .
C10 C -0.0408(7) -0.2254(7) 0.1536(3) 0.0269(10) Uani 1 1 d . . . . .
C11 C 0.0443(6) -0.0496(6) 0.1776(3) 0.0249(10) Uani 1 1 d . . . . .
H11 H 0.0605 0.0162 0.1297 0.030 Uiso 1 1 calc R U . . .
C12 C 0.1029(6) 0.0217(6) 0.2742(4) 0.0268(10) Uani 1 1 d . . . . .
C13 C 0.0864(7) -0.0753(6) 0.3466(3) 0.0264(10) Uani 1 1 d . . . . .
H13 H 0.1296 -0.0228 0.4120 0.032 Uiso 1 1 calc R U . . .
O1 O 0.0559(6) -0.2809(5) 0.4865(3) 0.0435(10) Uani 1 1 d . . . . .
H1 H 0.046(10) -0.346(9) 0.530(5) 0.065 Uiso 1 1 d . U . . .
O2 O -0.0729(5) -0.5220(5) 0.3745(2) 0.0354(8) Uani 1 1 d . . . . .
O3 O -0.2066(6) -0.4496(5) 0.0293(3) 0.0435(10) Uani 1 1 d . . . . .
O4 O -0.0667(7) -0.2249(6) -0.0104(3) 0.0503(11) Uani 1 1 d . . . . .
O5 O 0.1953(6) 0.2955(5) 0.2400(3) 0.0404(9) Uani 1 1 d D . . . .
O6 O 0.2665(5) 0.2592(5) 0.3908(3) 0.0399(9) Uani 1 1 d . . . . .
N2 N -0.1098(6) -0.3060(6) 0.0496(3) 0.0353(10) Uani 1 1 d . . . . .
N3 N 0.1958(6) 0.2054(5) 0.3038(3) 0.0300(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C4 2.098(5) . ?
N1 C1 1.383(7) . ?
C1 C6 1.375(7) . ?
C1 C2 1.382(7) . ?
C2 C3 1.371(7) . ?
C3 C4 1.384(7) . ?
C4 C5 1.387(7) . ?
C5 C6 1.370(7) . ?
C7 O2 1.243(6) . ?
C7 O1 1.269(6) . ?
C7 C8 1.494(6) . ?
C8 C13 1.383(6) . ?
C8 C9 1.393(7) . ?
C9 C10 1.375(6) . ?
C10 C11 1.391(7) . ?
C10 N2 1.474(6) . ?
C11 C12 1.359(7) . ?
C12 C13 1.378(6) . ?
C12 N3 1.465(6) . ?
O3 N2 1.225(5) . ?
O4 N2 1.219(5) . ?
O5 N3 1.213(5) . ?
O6 N3 1.226(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 117.6(5) . . ?
C6 C1 N1 122.2(5) . . ?
C2 C1 N1 120.2(5) . . ?
C3 C2 C1 121.7(5) . . ?
C2 C3 C4 119.5(5) . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 I1 119.6(3) . . ?
C5 C4 I1 120.7(4) . . ?
C6 C5 C4 119.2(5) . . ?
C5 C6 C1 122.2(5) . . ?
O2 C7 O1 124.8(4) . . ?
O2 C7 C8 119.1(4) . . ?
O1 C7 C8 116.1(4) . . ?
C13 C8 C9 119.7(4) . . ?
C13 C8 C7 120.1(4) . . ?
C9 C8 C7 120.2(4) . . ?
C10 C9 C8 118.5(4) . . ?
C9 C10 C11 122.7(4) . . ?
C9 C10 N2 118.6(4) . . ?
C11 C10 N2 118.7(4) . . ?
C12 C11 C10 117.0(4) . . ?
C11 C12 C13 122.6(4) . . ?
C11 C12 N3 119.4(4) . . ?
C13 C12 N3 117.9(4) . . ?
C12 C13 C8 119.5(4) . . ?
O4 N2 O3 124.4(4) . . ?
O4 N2 C10 117.6(4) . . ?
O3 N2 C10 117.9(4) . . ?
O5 N3 O6 124.2(4) . . ?
O5 N3 C12 117.3(4) . . ?
O6 N3 C12 118.5(4) . . ?

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
N1 H1B O6 0.82(8) 2.39(8) 3.191(7) 165(7) 2_556
N1 H1A O5 0.86(8) 2.55(8) 3.353(7) 156(7) 1_445
N1 H1A O6 0.86(8) 2.41(8) 3.154(6) 145(7) 1_445
C5 H5 I1 0.93 3.27 4.160(5) 162.1 2_455
C9 H9 I1 0.93 3.19 4.096(5) 166.6 1_545
C11 H11 O4 0.93 2.48 3.405(5) 171.0 2
O1 H1 O2 0.86(7) 1.78(7) 2.627(5) 169(7) 2_546

_refine_diff_density_max         0.876
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.147


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
####################################################################### 
# 
# 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_4IA_35DNBA_14
_database_code_depnum_ccdc_archive 'CCDC 1556547'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-iodoanilinium 3,5-dinitrobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6N1I1H7 1+, C7N2O6H3 1-'
_chemical_formula_sum            'C13 H10 I N3 O6'
_chemical_formula_weight         431.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.75880(10)
_cell_length_b                   12.0929(2)
_cell_length_c                   36.4619(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2980.16(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11815
_cell_measurement_theta_min      3.4910
_cell_measurement_theta_max      32.6580
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_F_000             1680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.185
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15628
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         3.065
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6082
_reflns_number_gt                5960
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.997

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogen atoms were refined anisotropically. Aromatic hydrogen 
atoms were placed in calculated positions and refined as riding on the 
atoms to which they were bonded. The hydrogen atoms of the two NH3+ groups 
were located using Fourier difference maps; H-atom positions were allowed 
to freely refine, but the Uiso of the H-atoms was constrained to 1.5Ueq 
of the N-atom to which they are bonded.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0179P)²+3.2869P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2475 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6082
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0476
_refine_ls_wR_factor_gt          0.0472
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.72077(4) 0.82438(2) -0.02451(2) 0.02046(7) Uani 1 1 d . . . . .
N1 N 1.7996(5) 1.0295(3) 0.13375(8) 0.0138(6) Uani 1 1 d . . . . .
H1A H 1.840(7) 1.102(4) 0.1336(13) 0.021 Uiso 1 1 d . U . . .
H1B H 1.686(8) 1.017(4) 0.1462(13) 0.021 Uiso 1 1 d . U . . .
H1C H 1.904(7) 0.998(4) 0.1447(14) 0.021 Uiso 1 1 d . U . . .
C1 C 1.7756(5) 0.9833(3) 0.09697(9) 0.0122(7) Uani 1 1 d . . . . .
C2 C 1.7908(5) 1.0511(3) 0.06655(10) 0.0144(7) Uani 1 1 d . . . . .
H2 H 1.8124 1.1266 0.0694 0.017 Uiso 1 1 calc R U . . .
C3 C 1.7733(6) 1.0054(3) 0.03178(9) 0.0151(7) Uani 1 1 d . . . . .
H3 H 1.7835 1.0500 0.0111 0.018 Uiso 1 1 calc R U . . .
C4 C 1.7406(5) 0.8931(3) 0.02826(9) 0.0131(6) Uani 1 1 d . . . . .
C5 C 1.7239(6) 0.8251(3) 0.05847(10) 0.0172(7) Uani 1 1 d . . . . .
H5 H 1.7020 0.7497 0.0556 0.021 Uiso 1 1 calc R U . . .
C6 C 1.7402(6) 0.8709(3) 0.09325(9) 0.0162(7) Uani 1 1 d . . . . .
H6 H 1.7275 0.8265 0.1139 0.019 Uiso 1 1 calc R U . . .
I2 I 1.24648(5) 1.04531(2) -0.04373(2) 0.03130(8) Uani 1 1 d . . . . .
N2 N 1.3145(5) 1.1810(3) 0.12224(9) 0.0144(6) Uani 1 1 d . . . . .
H2A H 1.425(7) 1.229(4) 0.1257(13) 0.022 Uiso 1 1 d . U . . .
H2B H 1.202(8) 1.208(4) 0.1290(13) 0.022 Uiso 1 1 d . U . . .
H2C H 1.346(7) 1.121(4) 0.1377(13) 0.022 Uiso 1 1 d . U . . .
C7 C 1.3098(5) 1.1486(3) 0.08395(10) 0.0140(7) Uani 1 1 d . . . . .
C8 C 1.3265(6) 1.2286(3) 0.05726(12) 0.0220(9) Uani 1 1 d . . . . .
H8 H 1.3454 1.3021 0.0638 0.026 Uiso 1 1 calc R U . . .
C9 C 1.3151(7) 1.1989(3) 0.02046(12) 0.0268(10) Uani 1 1 d . . . . .
H9 H 1.3281 1.2523 0.0022 0.032 Uiso 1 1 calc R U . . .
C10 C 1.2842(6) 1.0892(3) 0.01126(10) 0.0172(8) Uani 1 1 d . . . . .
C11 C 1.2703(6) 1.0087(3) 0.03803(10) 0.0167(7) Uani 1 1 d . . . . .
H11 H 1.2524 0.9351 0.0315 0.020 Uiso 1 1 calc R U . . .
C12 C 1.2834(6) 1.0382(3) 0.07481(10) 0.0156(7) Uani 1 1 d . . . . .
H12 H 1.2745 0.9846 0.0930 0.019 Uiso 1 1 calc R U . . .
C13 C 1.1882(5) 0.8180(3) 0.36470(10) 0.0136(7) Uani 1 1 d . . . . .
C14 C 1.1112(6) 0.9345(3) 0.35830(10) 0.0139(8) Uani 1 1 d . . . . .
C15 C 1.2296(6) 1.0091(3) 0.33988(9) 0.0135(7) Uani 1 1 d . . . . .
H15 H 1.3505 0.9868 0.3302 0.016 Uiso 1 1 calc R U . . .
C16 C 1.1671(5) 1.1169(3) 0.33594(10) 0.0134(8) Uani 1 1 d . . . . .
C17 C 0.9878(5) 1.1550(3) 0.34948(10) 0.0135(7) Uani 1 1 d . . . . .
H17 H 0.9488 1.2284 0.3471 0.016 Uiso 1 1 calc R U . . .
C18 C 0.8712(5) 1.0771(3) 0.36667(10) 0.0130(8) Uani 1 1 d . . . . .
C19 C 0.9276(5) 0.9680(3) 0.37123(10) 0.0122(7) Uani 1 1 d . . . . .
H19 H 0.8438 0.9179 0.3828 0.015 Uiso 1 1 calc R U . . .
O1 O 1.0688(4) 0.7453(2) 0.37497(8) 0.0185(6) Uani 1 1 d . . . . .
O2 O 1.3694(4) 0.8050(3) 0.35919(8) 0.0206(7) Uani 1 1 d . . . . .
O3 O 1.4478(4) 1.1584(2) 0.30256(8) 0.0240(7) Uani 1 1 d . . . . .
O4 O 1.2544(4) 1.29375(19) 0.31823(7) 0.0185(5) Uani 1 1 d . . . . .
O5 O 0.6371(5) 1.2106(3) 0.38041(10) 0.0308(8) Uani 1 1 d . . . . .
O6 O 0.5655(4) 1.0404(3) 0.39225(8) 0.0225(6) Uani 1 1 d . . . . .
N3 N 1.2992(5) 1.1951(3) 0.31728(8) 0.0160(6) Uani 1 1 d . . . . .
N4 N 0.6768(5) 1.1116(3) 0.38084(9) 0.0172(7) Uani 1 1 d . . . . .
C20 C 1.2913(5) 0.9566(3) 0.17837(9) 0.0130(7) Uani 1 1 d . . . . .
C21 C 1.3216(5) 0.8965(3) 0.21449(10) 0.0131(7) Uani 1 1 d . . . . .
C22 C 1.4930(5) 0.9148(3) 0.23473(10) 0.0140(7) Uani 1 1 d . . . . .
H22 H 1.5823 0.9698 0.2280 0.017 Uiso 1 1 calc R U . . .
C23 C 1.5268(5) 0.8491(3) 0.26503(10) 0.0143(8) Uani 1 1 d . . . . .
C24 C 1.4021(6) 0.7654(3) 0.27619(11) 0.0163(8) Uani 1 1 d . . . . .
H24 H 1.4322 0.7196 0.2959 0.020 Uiso 1 1 calc R U . . .
C25 C 1.2286(6) 0.7538(3) 0.25613(9) 0.0142(7) Uani 1 1 d . . . . .
C26 C 1.1855(5) 0.8181(3) 0.22567(10) 0.0137(7) Uani 1 1 d . . . . .
H26 H 1.0673 0.8086 0.2130 0.016 Uiso 1 1 calc R U . . .
O7 O 1.1386(4) 0.9350(2) 0.16044(7) 0.0163(6) Uani 1 1 d . . . . .
O8 O 1.4266(4) 1.0229(2) 0.16882(7) 0.0166(6) Uani 1 1 d . . . . .
O9 O 1.8092(5) 0.9487(3) 0.27909(9) 0.0367(8) Uani 1 1 d . . . . .
O10 O 1.7557(5) 0.7987(2) 0.30954(7) 0.0257(6) Uani 1 1 d . . . . .
O11 O 1.1282(5) 0.6101(3) 0.29377(8) 0.0269(7) Uani 1 1 d . . . . .
O12 O 0.9342(4) 0.6578(3) 0.24927(8) 0.0236(6) Uani 1 1 d . . . . .
N5 N 1.7113(5) 0.8669(3) 0.28615(9) 0.0203(7) Uani 1 1 d . . . . .
N6 N 1.0870(5) 0.6675(3) 0.26727(9) 0.0190(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C4 2.100(3) . ?
N1 C1 1.462(4) . ?
C1 C2 1.383(5) . ?
C1 C6 1.387(5) . ?
C2 C3 1.388(5) . ?
C3 C4 1.382(5) . ?
C4 C5 1.379(5) . ?
C5 C6 1.388(5) . ?
I2 C10 2.090(4) . ?
N2 C7 1.451(5) . ?
C7 C8 1.377(5) . ?
C7 C12 1.388(5) . ?
C8 C9 1.391(6) . ?
C9 C10 1.384(6) . ?
C10 C11 1.382(5) . ?
C11 C12 1.390(5) . ?
C13 O2 1.251(4) . ?
C13 O1 1.251(5) . ?
C13 C14 1.520(5) . ?
C14 C15 1.380(5) . ?
C14 C19 1.388(5) . ?
C15 C16 1.378(5) . ?
C16 C17 1.387(5) . ?
C16 N3 1.468(5) . ?
C17 C18 1.379(5) . ?
C18 C19 1.384(5) . ?
C18 N4 1.472(5) . ?
O3 N3 1.222(4) . ?
O4 N3 1.231(4) . ?
O5 N4 1.228(4) . ?
O6 N4 1.217(4) . ?
C20 O7 1.249(4) . ?
C20 O8 1.265(5) . ?
C20 C21 1.518(5) . ?
C21 C26 1.383(5) . ?
C21 C22 1.391(5) . ?
C22 C23 1.380(5) . ?
C23 C24 1.379(6) . ?
C23 N5 1.481(5) . ?
C24 C25 1.389(5) . ?
C25 C26 1.387(5) . ?
C25 N6 1.473(5) . ?
O9 N5 1.218(4) . ?
O10 N5 1.224(4) . ?
O11 N6 1.222(4) . ?
O12 N6 1.230(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.0(3) . . ?
C2 C1 N1 120.1(3) . . ?
C6 C1 N1 118.9(3) . . ?
C1 C2 C3 119.4(3) . . ?
C4 C3 C2 119.3(3) . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 I1 119.4(2) . . ?
C3 C4 I1 119.0(2) . . ?
C4 C5 C6 119.0(3) . . ?
C1 C6 C5 119.6(3) . . ?
C8 C7 C12 121.1(4) . . ?
C8 C7 N2 119.2(3) . . ?
C12 C7 N2 119.6(3) . . ?
C7 C8 C9 119.8(4) . . ?
C10 C9 C8 119.3(4) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 I2 119.4(3) . . ?
C9 C10 I2 119.6(3) . . ?
C10 C11 C12 119.8(3) . . ?
C7 C12 C11 119.1(3) . . ?
O2 C13 O1 126.2(4) . . ?
O2 C13 C14 115.3(4) . . ?
O1 C13 C14 118.4(3) . . ?
C15 C14 C19 119.5(3) . . ?
C15 C14 C13 118.8(3) . . ?
C19 C14 C13 121.6(3) . . ?
C16 C15 C14 119.4(3) . . ?
C15 C16 C17 123.0(4) . . ?
C15 C16 N3 118.1(3) . . ?
C17 C16 N3 118.8(3) . . ?
C18 C17 C16 115.7(3) . . ?
C17 C18 C19 123.3(3) . . ?
C17 C18 N4 118.5(3) . . ?
C19 C18 N4 118.3(3) . . ?
C18 C19 C14 118.9(3) . . ?
O3 N3 O4 124.5(3) . . ?
O3 N3 C16 118.0(3) . . ?
O4 N3 C16 117.5(3) . . ?
O6 N4 O5 124.0(3) . . ?
O6 N4 C18 118.1(3) . . ?
O5 N4 C18 117.8(3) . . ?
O7 C20 O8 125.9(3) . . ?
O7 C20 C21 117.7(3) . . ?
O8 C20 C21 116.4(3) . . ?
C26 C21 C22 120.4(3) . . ?
C26 C21 C20 119.6(3) . . ?
C22 C21 C20 119.8(3) . . ?
C23 C22 C21 118.1(4) . . ?
C24 C23 C22 123.9(3) . . ?
C24 C23 N5 117.9(3) . . ?
C22 C23 N5 118.2(3) . . ?
C23 C24 C25 115.8(3) . . ?
C26 C25 C24 122.8(3) . . ?
C26 C25 N6 118.8(3) . . ?
C24 C25 N6 118.4(3) . . ?
C21 C26 C25 118.8(3) . . ?
O9 N5 O10 124.2(3) . . ?
O9 N5 C23 117.7(3) . . ?
O10 N5 C23 118.1(3) . . ?
O11 N6 O12 124.0(3) . . ?
O11 N6 C25 118.2(3) . . ?
O12 N6 C25 117.8(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
N1 H1A O1 0.92(5) 1.87(5) 2.776(4) 171(4) 4_855
N1 H1B O8 0.90(5) 1.94(5) 2.828(4) 167(4) .
N1 H1C O7 0.90(5) 1.85(5) 2.739(4) 171(5) 1_655
C2 H2 O1 0.93 2.61 3.311(5) 132.3 4_855
C6 H6 O4 0.93 2.51 3.360(4) 152.4 4_845
N2 H2A O2 0.95(5) 1.76(5) 2.696(4) 169(5) 4_855
N2 H2B O1 0.86(5) 1.89(5) 2.706(4) 157(4) 4_755
N2 H2C O8 0.95(5) 1.73(5) 2.668(4) 172(4) .
C11 H11 I1 0.93 3.16 4.072(4) 169.0 3_465
C17 H17 O7 0.93 2.58 3.510(5) 176.7 4_755
C24 H24 O2 0.93 2.56 3.072(5) 114.8 .
C26 H26 O4 0.93 2.46 3.390(4) 176.3 4_745

_refine_diff_density_max         1.172
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.069


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_4Br2MA_35DNBA_23
_database_code_depnum_ccdc_archive 'CCDC 1556546'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'4-bromo-2-methylaniline 3,5-dinitrobenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7N1Br1H8, C7N2O6H4'
_chemical_formula_sum            'C14 H12 Br N3 O6'
_chemical_formula_weight         398.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1802(4)
_cell_length_b                   7.2420(4)
_cell_length_c                   14.7292(6)
_cell_angle_alpha                87.048(4)
_cell_angle_beta                 88.078(4)
_cell_angle_gamma                89.926(5)
_cell_volume                     764.46(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.05(10)
_cell_measurement_reflns_used    3677
_cell_measurement_theta_min      3.0680
_cell_measurement_theta_max      26.6220

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    2.727
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90875
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150.05(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11434
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.816
_diffrn_reflns_theta_max         30.410
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4107
_reflns_number_gt                3061
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogen atoms were refined anisotropically. Aromatic 
hydrogen atoms were placed in calculated positions and 
refined as riding on the atoms to which they were bonded. The hydrogen 
atoms of the NH2 group were located using Fourier difference maps and 
the positions and isotropic displacement parameters allowed to freely 
refine. The hydrogen atom of the carboxylic acid group was located using 
Fourier difference maps; the position was refined using a distance restraint 
(DFIX 0.9 Å) and the isotropic thermal parameters allowed to freely refine. 
The methyl group H-atoms were located initially using Fourier difference maps 
and the bond distances and angles constrained to take standard values; the 
Uiso of the H-atoms was constrained to 1.5Ueq of the C-atom to which they are 
bonded.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+0.0840P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4107
_refine_ls_number_parameters     230
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0926
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.25277(5) 0.63043(4) 0.45892(2) 0.03263(13) Uani 1 1 d . . . . .
C1 C 0.1504(4) 0.8071(4) 0.1555(2) 0.0205(6) Uani 1 1 d . . . . .
C2 C 0.0051(4) 0.8274(4) 0.2205(2) 0.0181(6) Uani 1 1 d . . . . .
C3 C 0.0387(4) 0.7755(4) 0.3116(2) 0.0210(6) Uani 1 1 d . . . . .
H3 H -0.0554 0.7875 0.3558 0.025 Uiso 1 1 calc R U . . .
C4 C 0.2105(5) 0.7066(4) 0.33599(19) 0.0206(6) Uani 1 1 d . . . . .
C5 C 0.3533(4) 0.6884(4) 0.2715(2) 0.0228(7) Uani 1 1 d . . . . .
H5 H 0.4687 0.6424 0.2885 0.027 Uiso 1 1 calc R U . . .
C6 C 0.3222(4) 0.7395(4) 0.1816(2) 0.0224(7) Uani 1 1 d . . . . .
H6 H 0.4177 0.7283 0.1380 0.027 Uiso 1 1 calc R U . . .
C7 C -0.1813(4) 0.9013(4) 0.1918(2) 0.0298(8) Uani 1 1 d . . . . .
H7B H -0.1637 1.0151 0.1562 0.045 Uiso 1 1 calc R U . . .
H7A H -0.2581 0.9230 0.2447 0.045 Uiso 1 1 calc R U . . .
H7C H -0.2408 0.8127 0.1560 0.045 Uiso 1 1 calc R U . . .
N1 N 0.1215(5) 0.8662(4) 0.06484(19) 0.0309(7) Uani 1 1 d . . . . .
H1A H 0.003(6) 0.855(5) 0.049(3) 0.057(13) Uiso 1 1 d . . . . .
H1B H 0.210(5) 0.831(4) 0.030(2) 0.022(9) Uiso 1 1 d . . . . .
H1 H 1.349(5) 0.068(5) 0.519(2) 0.055(13) Uiso 1 1 d D . . . .
C8 C 1.3764(4) 0.1079(4) 0.39859(19) 0.0170(6) Uani 1 1 d . . . . .
C9 C 1.2773(4) 0.1878(4) 0.31785(18) 0.0162(6) Uani 1 1 d . . . . .
C10 C 1.3693(4) 0.1864(4) 0.23303(19) 0.0170(6) Uani 1 1 d . . . . .
H10 H 1.4886 0.1372 0.2272 0.020 Uiso 1 1 calc R U . . .
C11 C 1.2801(4) 0.2593(4) 0.15800(19) 0.0189(6) Uani 1 1 d . . . . .
C12 C 1.1026(4) 0.3325(4) 0.16293(19) 0.0181(6) Uani 1 1 d . . . . .
H12 H 1.0450 0.3821 0.1115 0.022 Uiso 1 1 calc R U . . .
C13 C 1.0150(4) 0.3287(4) 0.24743(19) 0.0173(6) Uani 1 1 d . . . . .
C14 C 1.0984(4) 0.2586(4) 0.32583(19) 0.0179(6) Uani 1 1 d . . . . .
H14 H 1.0358 0.2592 0.3821 0.021 Uiso 1 1 calc R U . . .
O2 O 1.5337(3) 0.0444(3) 0.38969(13) 0.0227(5) Uani 1 1 d . . . . .
O1 O 1.2803(3) 0.1116(3) 0.47496(14) 0.0251(5) Uani 1 1 d D . . . .
N2 N 1.3781(4) 0.2612(4) 0.06866(17) 0.0270(6) Uani 1 1 d . . . . .
O3 O 1.5258(3) 0.1771(3) 0.06382(15) 0.0367(6) Uani 1 1 d . . . . .
O4 O 1.3067(4) 0.3441(4) 0.00436(15) 0.0427(7) Uani 1 1 d . . . . .
N3 N 0.8232(4) 0.4009(3) 0.25418(17) 0.0206(5) Uani 1 1 d . . . . .
O5 O 0.7460(3) 0.4425(3) 0.18296(15) 0.0296(5) Uani 1 1 d . . . . .
O6 O 0.7514(3) 0.4155(3) 0.32926(15) 0.0338(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.900(3) . ?
C1 C6 1.386(4) . ?
C1 N1 1.404(4) . ?
C1 C2 1.404(4) . ?
C2 C3 1.403(4) . ?
C2 C7 1.507(4) . ?
C3 C4 1.382(4) . ?
C4 C5 1.385(4) . ?
C5 C6 1.382(4) . ?
C8 O2 1.225(3) . ?
C8 O1 1.301(3) . ?
C8 C9 1.496(4) . ?
C9 C14 1.386(4) . ?
C9 C10 1.394(4) . ?
C10 C11 1.377(4) . ?
C11 C12 1.381(4) . ?
C11 N2 1.471(4) . ?
C12 C13 1.375(4) . ?
C13 C14 1.391(4) . ?
C13 N3 1.474(4) . ?
N2 O4 1.222(3) . ?
N2 O3 1.224(3) . ?
N3 O6 1.214(3) . ?
N3 O5 1.227(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 N1 120.7(3) . . ?
C6 C1 C2 120.4(3) . . ?
N1 C1 C2 118.8(3) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 C7 121.6(3) . . ?
C1 C2 C7 120.2(3) . . ?
C4 C3 C2 120.5(3) . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 Br1 120.2(2) . . ?
C5 C4 Br1 118.9(2) . . ?
C6 C5 C4 119.2(3) . . ?
C5 C6 C1 120.8(3) . . ?
O2 C8 O1 125.3(3) . . ?
O2 C8 C9 120.5(3) . . ?
O1 C8 C9 114.2(3) . . ?
C14 C9 C10 120.4(3) . . ?
C14 C9 C8 121.7(3) . . ?
C10 C9 C8 118.0(3) . . ?
C11 C10 C9 118.7(3) . . ?
C10 C11 C12 122.9(3) . . ?
C10 C11 N2 118.8(3) . . ?
C12 C11 N2 118.3(3) . . ?
C13 C12 C11 116.8(3) . . ?
C12 C13 C14 123.0(3) . . ?
C12 C13 N3 117.9(3) . . ?
C14 C13 N3 119.1(3) . . ?
C9 C14 C13 118.3(3) . . ?
O4 N2 O3 124.4(3) . . ?
O4 N2 C11 118.3(3) . . ?
O3 N2 C11 117.2(3) . . ?
O6 N3 O5 124.0(3) . . ?
O6 N3 C13 118.4(2) . . ?
O5 N3 C13 117.5(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
N1 H1B O3 0.85(3) 2.31(3) 3.136(4) 164(3) 2_765
O1 H1 O2 0.872(19) 1.77(2) 2.641(3) 172(4) 2_856

_refine_diff_density_max         1.339
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.099


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_4BrA_35DNBA_18
_database_code_depnum_ccdc_archive 'CCDC 1556550'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-bromoanilinium 3,5-dinitrobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6N1Br1H7 1+, C7N2O6H3 1-'
_chemical_formula_sum            'C13 H10 Br N3 O6'
_chemical_formula_weight         384.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.79370(10)
_cell_length_b                   11.95740(10)
_cell_length_c                   35.8729(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2914.13(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150
_cell_measurement_reflns_used    11361
_cell_measurement_theta_min      3.8840
_cell_measurement_theta_max      71.8380

_exptl_crystal_description       needle
_exptl_crystal_colour            colourles
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    4.205
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.44877
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14999
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         4.444
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_full        66.600
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5107
_reflns_number_gt                4983
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.982

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogen atoms were refined anisotropically. Aromatic 
hydrogen atoms were placed in calculated positions and 
refined as riding on the atoms to which they were bonded. The hydrogen 
atoms of the two NH3+ groups were located using Fourier difference 
maps; H-atom positions were allowed to freely refine, but the Uiso 
of the H-atoms was constrained to 1.5Ueq of the N-atom to which they 
are bound.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0746P)²+1.4793P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2035 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.028(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5107
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.30746(9) 0.67590(4) 0.47726(2) 0.03575(18) Uani 1 1 d . . . . .
N1 N 1.1962(6) 0.4667(3) 0.63086(11) 0.0187(7) Uani 1 1 d . . . . .
H1A H 1.168(9) 0.407(6) 0.6304(17) 0.028 Uiso 1 1 d . U . . .
H1B H 1.301(10) 0.476(5) 0.6452(17) 0.028 Uiso 1 1 d . U . . .
H1C H 1.107(10) 0.497(5) 0.6417(17) 0.028 Uiso 1 1 d . U . . .
C1 C 1.2242(6) 0.5159(3) 0.59399(12) 0.0167(8) Uani 1 1 d . . . . .
C2 C 1.2100(7) 0.4495(3) 0.56257(13) 0.0205(9) Uani 1 1 d . . . . .
H2 H 1.1849 0.3734 0.5649 0.025 Uiso 1 1 calc R U . . .
C3 C 1.2332(7) 0.4971(4) 0.52766(13) 0.0233(9) Uani 1 1 d . . . . .
H3 H 1.2221 0.4539 0.5062 0.028 Uiso 1 1 calc R U . . .
C4 C 1.2737(6) 0.6109(4) 0.52534(13) 0.0207(9) Uani 1 1 d . . . . .
C5 C 1.2914(7) 0.6769(4) 0.55642(14) 0.0267(10) Uani 1 1 d . . . . .
H5 H 1.3192 0.7528 0.5542 0.032 Uiso 1 1 calc R U . . .
C6 C 1.2673(7) 0.6290(4) 0.59100(13) 0.0248(10) Uani 1 1 d . . . . .
H6 H 1.2799 0.6724 0.6124 0.030 Uiso 1 1 calc R U . . .
Br2 Br 0.76096(12) 0.46677(6) 0.45692(2) 0.0504(2) Uani 1 1 d . . . . .
N2 N 0.6797(7) 0.3140(4) 0.61794(12) 0.0220(8) Uani 1 1 d . . . . .
H2A H 0.591(11) 0.273(6) 0.6210(19) 0.033 Uiso 1 1 d . U . . .
H2B H 0.779(11) 0.284(5) 0.6219(19) 0.033 Uiso 1 1 d . U . . .
H2C H 0.662(10) 0.362(6) 0.6310(19) 0.033 Uiso 1 1 d . U . . .
C7 C 0.6858(6) 0.3514(4) 0.57947(13) 0.0198(9) Uani 1 1 d . . . . .
C8 C 0.6654(8) 0.2743(4) 0.55118(15) 0.0309(11) Uani 1 1 d . . . . .
H8 H 0.6413 0.1995 0.5567 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6813(9) 0.3093(4) 0.51444(15) 0.0361(12) Uani 1 1 d . . . . .
H9 H 0.6660 0.2586 0.4950 0.043 Uiso 1 1 calc R U . . .
C10 C 0.7198(8) 0.4193(4) 0.50725(14) 0.0294(10) Uani 1 1 d . . . . .
C11 C 0.7362(7) 0.4987(4) 0.53518(14) 0.0250(10) Uani 1 1 d . . . . .
H11 H 0.7591 0.5735 0.5294 0.030 Uiso 1 1 calc R U . . .
C12 C 0.7178(7) 0.4643(4) 0.57177(13) 0.0211(9) Uani 1 1 d . . . . .
H12 H 0.7267 0.5159 0.5911 0.025 Uiso 1 1 calc R U . . .
C13 C 0.1809(7) 0.1771(4) 0.63026(13) 0.0213(9) Uani 1 1 d . . . . .
C14 C 0.1061(7) 0.0597(4) 0.63749(13) 0.0197(9) Uani 1 1 d . . . . .
C15 C 0.2269(6) -0.0135(4) 0.65711(13) 0.0202(9) Uani 1 1 d . . . . .
H15 H 0.3471 0.0105 0.6666 0.024 Uiso 1 1 calc R U . . .
C16 C 0.1648(6) -0.1227(3) 0.66226(12) 0.0177(8) Uani 1 1 d . . . . .
C17 C -0.0129(7) -0.1631(4) 0.64901(12) 0.0196(9) Uani 1 1 d . . . . .
H17 H -0.0516 -0.2371 0.6524 0.024 Uiso 1 1 calc R U . . .
C18 C -0.1291(6) -0.0862(4) 0.63049(12) 0.0182(9) Uani 1 1 d . . . . .
C19 C -0.0740(7) 0.0240(4) 0.62463(12) 0.0194(9) Uani 1 1 d . . . . .
H19 H -0.1575 0.0731 0.6122 0.023 Uiso 1 1 calc R U . . .
O1 O 0.0588(5) 0.2497(3) 0.61918(10) 0.0272(8) Uani 1 1 d . . . . .
O2 O 0.3594(5) 0.1931(3) 0.63566(11) 0.0329(8) Uani 1 1 d . . . . .
O3 O 0.4428(5) -0.1603(3) 0.69763(12) 0.0364(9) Uani 1 1 d . . . . .
O4 O 0.2541(5) -0.2990(3) 0.68205(10) 0.0277(7) Uani 1 1 d . . . . .
O5 O -0.3606(7) -0.2234(3) 0.61887(15) 0.0516(13) Uani 1 1 d . . . . .
O6 O -0.4328(5) -0.0548(3) 0.60351(11) 0.0349(9) Uani 1 1 d . . . . .
N3 N 0.2966(6) -0.1994(3) 0.68220(11) 0.0219(8) Uani 1 1 d . . . . .
N4 N -0.3216(6) -0.1235(3) 0.61634(12) 0.0262(9) Uani 1 1 d . . . . .
C20 C 0.7054(6) 0.5365(3) 0.67712(12) 0.0179(8) Uani 1 1 d . . . . .
C21 C 0.6753(6) 0.5943(3) 0.71393(13) 0.0180(8) Uani 1 1 d . . . . .
C22 C 0.5059(6) 0.5761(4) 0.73481(13) 0.0192(9) Uani 1 1 d . . . . .
H22 H 0.4163 0.5212 0.7278 0.023 Uiso 1 1 calc R U . . .
C23 C 0.4723(7) 0.6407(4) 0.76615(13) 0.0216(9) Uani 1 1 d . . . . .
C24 C 0.5998(7) 0.7238(4) 0.77780(13) 0.0241(10) Uani 1 1 d . . . . .
H24 H 0.5715 0.7690 0.7982 0.029 Uiso 1 1 calc R U . . .
C25 C 0.7712(7) 0.7364(4) 0.75759(13) 0.0208(9) Uani 1 1 d . . . . .
C26 C 0.8132(6) 0.6733(4) 0.72621(12) 0.0196(8) Uani 1 1 d . . . . .
H26 H 0.9312 0.6832 0.7135 0.023 Uiso 1 1 calc R U . . .
O7 O 0.8576(5) 0.5582(3) 0.65908(9) 0.0218(7) Uani 1 1 d . . . . .
O8 O 0.5688(5) 0.4706(3) 0.66681(9) 0.0235(7) Uani 1 1 d . . . . .
O9 O 0.1879(6) 0.5430(4) 0.77921(13) 0.0488(11) Uani 1 1 d . . . . .
O10 O 0.2525(6) 0.6880(4) 0.81282(11) 0.0410(9) Uani 1 1 d . . . . .
O11 O 0.8744(6) 0.8786(4) 0.79649(11) 0.0416(10) Uani 1 1 d . . . . .
O12 O 1.0656(5) 0.8322(3) 0.75110(11) 0.0360(9) Uani 1 1 d . . . . .
N5 N 0.2916(6) 0.6225(4) 0.78775(11) 0.0280(9) Uani 1 1 d . . . . .
N6 N 0.9148(6) 0.8227(4) 0.76932(12) 0.0269(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.906(4) . ?
N1 C1 1.460(6) . ?
N1 H1A 0.74(7) . ?
N1 H1B 0.88(7) . ?
N1 H1C 0.81(7) . ?
C1 C2 1.382(6) . ?
C1 C6 1.387(6) . ?
C2 C3 1.385(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(7) . ?
C5 C6 1.377(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
Br2 C10 1.913(5) . ?
N2 C7 1.451(6) . ?
N2 H2A 0.79(8) . ?
N2 H2B 0.77(8) . ?
N2 H2C 0.75(7) . ?
C7 C8 1.379(7) . ?
C7 C12 1.395(6) . ?
C8 C9 1.387(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.366(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(7) . ?
C11 C12 1.381(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O2 1.243(6) . ?
C13 O1 1.265(6) . ?
C13 C14 1.515(6) . ?
C14 C19 1.375(7) . ?
C14 C15 1.391(7) . ?
C15 C16 1.385(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(6) . ?
C16 N3 1.468(5) . ?
C17 C18 1.382(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(6) . ?
C18 N4 1.472(6) . ?
C19 H19 0.9300 . ?
O3 N3 1.229(5) . ?
O4 N3 1.226(5) . ?
O5 N4 1.226(6) . ?
O6 N4 1.207(6) . ?
C20 O7 1.247(5) . ?
C20 O8 1.273(5) . ?
C20 C21 1.504(6) . ?
C21 C22 1.390(6) . ?
C21 C26 1.401(7) . ?
C22 C23 1.383(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(7) . ?
C23 N5 1.468(6) . ?
C24 C25 1.380(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(6) . ?
C25 N6 1.482(6) . ?
C26 H26 0.9300 . ?
O9 N5 1.222(6) . ?
O10 N5 1.222(6) . ?
O11 N6 1.213(6) . ?
O12 N6 1.221(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1A 114(5) . . ?
C1 N1 H1B 112(4) . . ?
H1A N1 H1B 110(6) . . ?
C1 N1 H1C 111(4) . . ?
H1A N1 H1C 105(7) . . ?
H1B N1 H1C 106(5) . . ?
C2 C1 C6 120.8(4) . . ?
C2 C1 N1 119.8(4) . . ?
C6 C1 N1 119.4(4) . . ?
C1 C2 C3 119.6(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 118.6(4) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 122.2(4) . . ?
C5 C4 Br1 119.4(3) . . ?
C3 C4 Br1 118.5(4) . . ?
C4 C5 C6 118.8(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C7 N2 H2A 110(5) . . ?
C7 N2 H2B 107(5) . . ?
H2A N2 H2B 111(6) . . ?
C7 N2 H2C 111(5) . . ?
H2A N2 H2C 106(7) . . ?
H2B N2 H2C 112(7) . . ?
C8 C7 C12 121.2(4) . . ?
C8 C7 N2 119.4(4) . . ?
C12 C7 N2 119.4(4) . . ?
C7 C8 C9 119.3(5) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 119.0(5) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 122.6(5) . . ?
C9 C10 Br2 119.5(4) . . ?
C11 C10 Br2 117.8(4) . . ?
C12 C11 C10 118.4(4) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C7 119.4(4) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
O2 C13 O1 125.7(5) . . ?
O2 C13 C14 116.3(4) . . ?
O1 C13 C14 118.0(4) . . ?
C19 C14 C15 120.0(4) . . ?
C19 C14 C13 121.9(4) . . ?
C15 C14 C13 118.1(4) . . ?
C16 C15 C14 118.8(4) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 123.3(4) . . ?
C15 C16 N3 117.9(4) . . ?
C17 C16 N3 118.8(4) . . ?
C18 C17 C16 115.5(4) . . ?
C18 C17 H17 122.3 . . ?
C16 C17 H17 122.3 . . ?
C17 C18 C19 123.5(4) . . ?
C17 C18 N4 118.1(4) . . ?
C19 C18 N4 118.4(4) . . ?
C14 C19 C18 119.0(4) . . ?
C14 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
O4 N3 O3 124.2(4) . . ?
O4 N3 C16 117.4(4) . . ?
O3 N3 C16 118.3(4) . . ?
O6 N4 O5 123.7(4) . . ?
O6 N4 C18 118.8(4) . . ?
O5 N4 C18 117.5(4) . . ?
O7 C20 O8 125.6(4) . . ?
O7 C20 C21 118.2(4) . . ?
O8 C20 C21 116.1(4) . . ?
C22 C21 C26 119.3(4) . . ?
C22 C21 C20 120.9(4) . . ?
C26 C21 C20 119.6(4) . . ?
C23 C22 C21 119.2(4) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 122.9(4) . . ?
C22 C23 N5 119.0(4) . . ?
C24 C23 N5 118.1(4) . . ?
C25 C24 C23 116.6(4) . . ?
C25 C24 H24 121.7 . . ?
C23 C24 H24 121.7 . . ?
C24 C25 C26 122.8(4) . . ?
C24 C25 N6 118.8(4) . . ?
C26 C25 N6 118.4(4) . . ?
C25 C26 C21 119.0(4) . . ?
C25 C26 H26 120.5 . . ?
C21 C26 H26 120.5 . . ?
O10 N5 O9 123.9(4) . . ?
O10 N5 C23 118.4(4) . . ?
O9 N5 C23 117.7(4) . . ?
O11 N6 O12 124.7(4) . . ?
O11 N6 C25 117.6(4) . . ?
O12 N6 C25 117.7(4) . . ?

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
N1 H1A O1 0.74(7) 2.06(7) 2.789(5) 168(7) 1_655
N1 H1B O8 0.88(7) 1.98(7) 2.841(5) 165(6) 1_655
N1 H1C O7 0.81(7) 1.94(7) 2.741(5) 167(6) .
C2 H2 O1 0.93 2.59 3.300(5) 133.3 1_655
C6 H6 O4 0.93 2.53 3.379(6) 152.1 1_665
N2 H2A O2 0.79(8) 1.91(8) 2.689(6) 169(7) .
N2 H2B O1 0.77(8) 1.95(8) 2.689(6) 159(7) 1_655
N2 H2C O8 0.75(7) 1.93(7) 2.673(5) 168(7) .
C11 H11 Br1 0.93 3.02 3.946(5) 171.0 4_466
C12 H12 O7 0.93 2.64 3.460(6) 146.7 .
C17 H17 O7 0.93 2.54 3.465(5) 176.9 1_445
C24 H24 O2 0.93 2.58 3.138(6) 118.8 3_656
C26 H26 O4 0.93 2.48 3.404(6) 176.6 1_665

_refine_diff_density_max         1.205
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.087


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_4BrA_35DNBA_19
_database_code_depnum_ccdc_archive 'CCDC 1556549'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2019-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-bromoaniline 3,5-dinitrobenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6N1Br1H6, C7N2O6H4'
_chemical_formula_sum            'C13 H10 Br N3 O6'
_chemical_formula_weight         384.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3332(10)
_cell_length_b                   13.937(2)
_cell_length_c                   15.611(2)
_cell_angle_alpha                65.133(5)
_cell_angle_beta                 82.758(6)
_cell_angle_gamma                83.330(6)
_cell_volume                     1432.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    22003
_cell_measurement_theta_min      6.09
_cell_measurement_theta_max      55.22

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    2.907
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6416
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, Rigaku 1995'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
'Rigaku R-AXIS RAPID IP Image Plate diffractometer'
;
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34237
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.045
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6545
_reflns_number_gt                5473
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogen atoms were refined anisotropically. Aromatic 
hydrogen atoms were placed in calculated positions and 
refined as riding on the atoms to which they were bonded. The 
hydrogen atoms of the NH2 group were identified using Fourier 
difference maps; the positions were allowed to freely refine, 
but the Uiso of the H-atoms was constrained to 1.5Ueq of the 
N-atom to which they are bonded. The hydrogen atoms of the 
carboxylic acid groups were located using Fourier difference 
maps and the positions refined using a distance restraint 
(DFIX 0.9 A); the Uiso of the H-atom was constrained to 
1.5Ueq of the O-atom to which it is bonded.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.0449P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6545
_refine_ls_number_parameters     433
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.14412(3) -0.12195(2) 0.35275(2) 0.03224(8) Uani 1 1 d . . . . .
N1 N 0.5661(3) 0.15330(18) 0.09188(16) 0.0350(5) Uani 1 1 d . . . . .
H1B H 0.629(4) 0.193(2) 0.035(2) 0.053 Uiso 1 1 d . U . . .
H1A H 0.479(4) 0.163(2) 0.113(2) 0.053 Uiso 1 1 d . U . . .
C1 C 0.6989(3) 0.09325(17) 0.15220(15) 0.0257(5) Uani 1 1 d . . . . .
C2 C 0.6496(3) 0.03234(17) 0.24798(15) 0.0257(4) Uani 1 1 d . . . . .
H2 H 0.5271 0.0342 0.2718 0.031 Uiso 1 1 calc R U . . .
C3 C 0.7814(3) -0.03067(17) 0.30765(15) 0.0250(4) Uani 1 1 d . . . . .
H3 H 0.7482 -0.0705 0.3714 0.030 Uiso 1 1 calc R U . . .
C4 C 0.9634(3) -0.03381(16) 0.27148(14) 0.0241(4) Uani 1 1 d . . . . .
C5 C 1.0157(3) 0.02652(17) 0.17716(15) 0.0265(5) Uani 1 1 d . . . . .
H5 H 1.1384 0.0244 0.1536 0.032 Uiso 1 1 calc R U . . .
C6 C 0.8834(3) 0.09000(18) 0.11834(15) 0.0282(5) Uani 1 1 d . . . . .
H6 H 0.9182 0.1313 0.0550 0.034 Uiso 1 1 calc R U . . .
Br2 Br 0.78587(3) 0.65913(2) 0.02589(2) 0.03314(8) Uani 1 1 d . . . . .
N2 N 0.9273(3) 0.36268(18) 0.42999(15) 0.0378(5) Uani 1 1 d . . . . .
H2A H 0.844(5) 0.355(2) 0.470(2) 0.057 Uiso 1 1 d . U . . .
H2B H 1.025(5) 0.339(2) 0.443(2) 0.057 Uiso 1 1 d . U . . .
C7 C 0.8943(3) 0.42954(17) 0.33793(15) 0.0263(5) Uani 1 1 d . . . . .
C8 C 1.0370(3) 0.45165(17) 0.26576(15) 0.0274(5) Uani 1 1 d . . . . .
H8 H 1.1551 0.4211 0.2800 0.033 Uiso 1 1 calc R U . . .
C9 C 1.0048(3) 0.51847(17) 0.17331(15) 0.0278(5) Uani 1 1 d . . . . .
H9 H 1.1005 0.5327 0.1255 0.033 Uiso 1 1 calc R U . . .
C10 C 0.8284(3) 0.56402(16) 0.15251(15) 0.0254(4) Uani 1 1 d . . . . .
C11 C 0.6846(3) 0.54361(17) 0.22297(15) 0.0257(4) Uani 1 1 d . . . . .
H11 H 0.5671 0.5751 0.2084 0.031 Uiso 1 1 calc R U . . .
C12 C 0.7174(3) 0.47603(17) 0.31501(15) 0.0252(4) Uani 1 1 d . . . . .
H12 H 0.6208 0.4612 0.3624 0.030 Uiso 1 1 calc R U . . .
C13 C 0.5913(3) 0.39291(17) 0.11226(15) 0.0247(4) Uani 1 1 d . . . . .
C14 C 0.6666(3) 0.31411(16) 0.20060(14) 0.0216(4) Uani 1 1 d . . . . .
C15 C 0.5522(3) 0.27902(16) 0.28425(14) 0.0229(4) Uani 1 1 d . . . . .
H15 H 0.4288 0.3037 0.2847 0.028 Uiso 1 1 calc R U . . .
C16 C 0.6242(3) 0.20719(16) 0.36631(14) 0.0221(4) Uani 1 1 d . . . . .
C17 C 0.8073(3) 0.16995(16) 0.37013(14) 0.0235(4) Uani 1 1 d . . . . .
H17 H 0.8537 0.1219 0.4264 0.028 Uiso 1 1 calc R U . . .
C18 C 0.9175(3) 0.20773(16) 0.28619(15) 0.0238(4) Uani 1 1 d . . . . .
C19 C 0.8521(3) 0.27807(16) 0.20069(15) 0.0240(4) Uani 1 1 d . . . . .
H19 H 0.9297 0.3005 0.1450 0.029 Uiso 1 1 calc R U . . .
O1 O 0.6929(2) 0.41075(13) 0.03519(10) 0.0310(4) Uani 1 1 d D . . . .
H1 H 0.649(4) 0.4622(18) -0.0182(14) 0.046 Uiso 1 1 d D U . . .
O2 O 0.4352(2) 0.43826(12) 0.11733(10) 0.0294(3) Uani 1 1 d . . . . .
O3 O 0.3513(2) 0.21933(13) 0.45433(11) 0.0335(4) Uani 1 1 d . . . . .
O4 O 0.5560(2) 0.09252(14) 0.52172(11) 0.0369(4) Uani 1 1 d . . . . .
O5 O 1.1736(2) 0.11416(13) 0.36241(11) 0.0357(4) Uani 1 1 d . . . . .
O6 O 1.2107(2) 0.20835(13) 0.21117(11) 0.0328(4) Uani 1 1 d . . . . .
N3 N 0.5008(2) 0.16973(15) 0.45394(12) 0.0276(4) Uani 1 1 d . . . . .
N4 N 1.1149(2) 0.17368(14) 0.28680(13) 0.0275(4) Uani 1 1 d . . . . .
C20 C 0.3780(3) 0.10155(16) 0.89678(14) 0.0230(4) Uani 1 1 d . . . . .
C21 C 0.2810(3) 0.18094(16) 0.81541(14) 0.0223(4) Uani 1 1 d . . . . .
C22 C 0.3787(3) 0.22697(16) 0.72743(14) 0.0223(4) Uani 1 1 d . . . . .
H22 H 0.5034 0.2082 0.7190 0.027 Uiso 1 1 calc R U . . .
C23 C 0.2867(3) 0.30108(16) 0.65289(14) 0.0234(4) Uani 1 1 d . . . . .
C24 C 0.1017(3) 0.33252(16) 0.66145(15) 0.0240(4) Uani 1 1 d . . . . .
H24 H 0.0424 0.3833 0.6105 0.029 Uiso 1 1 calc R U . . .
C25 C 0.0101(3) 0.28398(16) 0.75032(15) 0.0244(4) Uani 1 1 d . . . . .
C26 C 0.0947(3) 0.20892(17) 0.82687(15) 0.0249(4) Uani 1 1 d . . . . .
H26 H 0.0281 0.1774 0.8853 0.030 Uiso 1 1 calc R U . . .
N5 N 0.3915(3) 0.35208(15) 0.56044(12) 0.0284(4) Uani 1 1 d . . . . .
N6 N -0.1864(2) 0.31615(15) 0.76342(14) 0.0290(4) Uani 1 1 d . . . . .
O7 O 0.2802(2) 0.05943(12) 0.97510(10) 0.0286(3) Uani 1 1 d D . . . .
H7 H 0.344(3) 0.0111(18) 1.0218(15) 0.043 Uiso 1 1 d D U . . .
O8 O 0.5483(2) 0.08152(12) 0.88459(10) 0.0280(3) Uani 1 1 d . . . . .
O9 O 0.5495(2) 0.31591(13) 0.55110(11) 0.0337(4) Uani 1 1 d . . . . .
O10 O 0.3163(2) 0.42740(14) 0.49838(11) 0.0432(5) Uani 1 1 d . . . . .
O11 O -0.2648(2) 0.37310(13) 0.69274(12) 0.0367(4) Uani 1 1 d . . . . .
O12 O -0.2600(2) 0.28423(13) 0.84463(12) 0.0367(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.900(2) . ?
N1 C1 1.384(3) . ?
N1 H1B 0.92(3) . ?
N1 H1A 0.71(3) . ?
C1 C6 1.392(3) . ?
C1 C2 1.398(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
Br2 C10 1.902(2) . ?
N2 C7 1.379(3) . ?
N2 H2A 0.80(3) . ?
N2 H2B 0.77(3) . ?
C7 C8 1.394(3) . ?
C7 C12 1.399(3) . ?
C8 C9 1.382(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(3) . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O2 1.252(2) . ?
C13 O1 1.277(2) . ?
C13 C14 1.480(3) . ?
C14 C15 1.390(3) . ?
C14 C19 1.394(3) . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(3) . ?
C16 N3 1.470(3) . ?
C17 C18 1.378(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(3) . ?
C18 N4 1.470(2) . ?
C19 H19 0.9300 . ?
O1 H1 0.906(17) . ?
O3 N3 1.227(2) . ?
O4 N3 1.221(2) . ?
O5 N4 1.220(2) . ?
O6 N4 1.229(2) . ?
C20 O8 1.256(2) . ?
C20 O7 1.275(2) . ?
C20 C21 1.486(3) . ?
C21 C26 1.387(3) . ?
C21 C22 1.389(3) . ?
C22 C23 1.379(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.384(3) . ?
C23 N5 1.471(3) . ?
C24 C25 1.383(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(3) . ?
C25 N6 1.474(3) . ?
C26 H26 0.9300 . ?
N5 O10 1.221(2) . ?
N5 O9 1.225(2) . ?
N6 O11 1.223(2) . ?
N6 O12 1.227(2) . ?
O7 H7 0.895(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1B 106.3(18) . . ?
C1 N1 H1A 118(3) . . ?
H1B N1 H1A 130(3) . . ?
N1 C1 C6 120.8(2) . . ?
N1 C1 C2 120.6(2) . . ?
C6 C1 C2 118.64(19) . . ?
C3 C2 C1 120.62(19) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.40(19) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 121.00(19) . . ?
C5 C4 Br1 119.49(16) . . ?
C3 C4 Br1 119.50(16) . . ?
C6 C5 C4 119.17(19) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 121.14(19) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C7 N2 H2A 118(2) . . ?
C7 N2 H2B 121(2) . . ?
H2A N2 H2B 121(3) . . ?
N2 C7 C8 120.5(2) . . ?
N2 C7 C12 120.8(2) . . ?
C8 C7 C12 118.74(19) . . ?
C9 C8 C7 120.76(19) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.38(19) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.94(19) . . ?
C11 C10 Br2 119.74(16) . . ?
C9 C10 Br2 119.29(16) . . ?
C12 C11 C10 119.37(19) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C7 120.80(19) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
O2 C13 O1 124.27(19) . . ?
O2 C13 C14 118.86(18) . . ?
O1 C13 C14 116.86(18) . . ?
C15 C14 C19 120.21(19) . . ?
C15 C14 C13 119.35(18) . . ?
C19 C14 C13 120.39(18) . . ?
C16 C15 C14 118.94(19) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 122.96(19) . . ?
C15 C16 N3 118.29(18) . . ?
C17 C16 N3 118.74(18) . . ?
C18 C17 C16 116.54(19) . . ?
C18 C17 H17 121.7 . . ?
C16 C17 H17 121.7 . . ?
C17 C18 C19 123.24(19) . . ?
C17 C18 N4 118.84(18) . . ?
C19 C18 N4 117.91(18) . . ?
C18 C19 C14 118.07(19) . . ?
C18 C19 H19 121.0 . . ?
C14 C19 H19 121.0 . . ?
C13 O1 H1 116.5(17) . . ?
O4 N3 O3 124.67(18) . . ?
O4 N3 C16 117.55(17) . . ?
O3 N3 C16 117.76(17) . . ?
O5 N4 O6 124.21(18) . . ?
O5 N4 C18 118.00(18) . . ?
O6 N4 C18 117.78(17) . . ?
O8 C20 O7 124.74(19) . . ?
O8 C20 C21 118.64(18) . . ?
O7 C20 C21 116.61(18) . . ?
C26 C21 C22 120.17(19) . . ?
C26 C21 C20 120.51(18) . . ?
C22 C21 C20 119.32(18) . . ?
C23 C22 C21 118.51(19) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C22 C23 C24 123.26(19) . . ?
C22 C23 N5 118.45(18) . . ?
C24 C23 N5 118.25(18) . . ?
C25 C24 C23 116.05(19) . . ?
C25 C24 H24 122.0 . . ?
C23 C24 H24 122.0 . . ?
C26 C25 C24 123.11(19) . . ?
C26 C25 N6 118.80(19) . . ?
C24 C25 N6 118.08(18) . . ?
C25 C26 C21 118.89(19) . . ?
C25 C26 H26 120.6 . . ?
C21 C26 H26 120.6 . . ?
O10 N5 O9 124.36(18) . . ?
O10 N5 C23 118.18(18) . . ?
O9 N5 C23 117.46(17) . . ?
O11 N6 O12 124.45(18) . . ?
O11 N6 C25 117.84(18) . . ?
O12 N6 C25 117.71(18) . . ?
C20 O7 H7 113.6(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 177.7(2) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C2 C3 C4 Br1 -179.00(17) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
Br1 C4 C5 C6 179.64(17) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
N1 C1 C6 C5 -177.0(2) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
N2 C7 C8 C9 179.9(2) . . . . ?
C12 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C8 C9 C10 Br2 178.20(17) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
Br2 C10 C11 C12 -178.78(16) . . . . ?
C10 C11 C12 C7 1.0(3) . . . . ?
N2 C7 C12 C11 179.5(2) . . . . ?
C8 C7 C12 C11 -0.8(3) . . . . ?
O2 C13 C14 C15 10.9(3) . . . . ?
O1 C13 C14 C15 -169.9(2) . . . . ?
O2 C13 C14 C19 -167.0(2) . . . . ?
O1 C13 C14 C19 12.3(3) . . . . ?
C19 C14 C15 C16 -1.0(3) . . . . ?
C13 C14 C15 C16 -178.87(19) . . . . ?
C14 C15 C16 C17 1.7(3) . . . . ?
C14 C15 C16 N3 -179.17(19) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
N3 C16 C17 C18 -179.76(19) . . . . ?
C16 C17 C18 C19 -1.1(3) . . . . ?
C16 C17 C18 N4 177.83(18) . . . . ?
C17 C18 C19 C14 1.7(3) . . . . ?
N4 C18 C19 C14 -177.26(19) . . . . ?
C15 C14 C19 C18 -0.6(3) . . . . ?
C13 C14 C19 C18 177.24(19) . . . . ?
C15 C16 N3 O4 166.8(2) . . . . ?
C17 C16 N3 O4 -14.1(3) . . . . ?
C15 C16 N3 O3 -14.5(3) . . . . ?
C17 C16 N3 O3 164.7(2) . . . . ?
C17 C18 N4 O5 -1.0(3) . . . . ?
C19 C18 N4 O5 177.99(19) . . . . ?
C17 C18 N4 O6 -179.98(19) . . . . ?
C19 C18 N4 O6 -1.0(3) . . . . ?
O8 C20 C21 C26 -177.1(2) . . . . ?
O7 C20 C21 C26 2.1(3) . . . . ?
O8 C20 C21 C22 3.0(3) . . . . ?
O7 C20 C21 C22 -177.8(2) . . . . ?
C26 C21 C22 C23 0.6(3) . . . . ?
C20 C21 C22 C23 -179.52(19) . . . . ?
C21 C22 C23 C24 0.4(3) . . . . ?
C21 C22 C23 N5 178.22(19) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
N5 C23 C24 C25 -178.57(19) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C23 C24 C25 N6 178.96(19) . . . . ?
C24 C25 C26 C21 0.8(3) . . . . ?
N6 C25 C26 C21 -178.01(19) . . . . ?
C22 C21 C26 C25 -1.1(3) . . . . ?
C20 C21 C26 C25 178.9(2) . . . . ?
C22 C23 N5 O10 -170.3(2) . . . . ?
C24 C23 N5 O10 7.6(3) . . . . ?
C22 C23 N5 O9 9.6(3) . . . . ?
C24 C23 N5 O9 -172.5(2) . . . . ?
C26 C25 N6 O11 -171.4(2) . . . . ?
C24 C25 N6 O11 9.8(3) . . . . ?
C26 C25 N6 O12 8.9(3) . . . . ?
C24 C25 N6 O12 -170.0(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
N1 H1A Br2 0.71(3) 3.16(3) 3.530(2) 116(3) 2_665
N1 H1A O6 0.71(3) 2.53(3) 3.219(3) 167(3) 1_455
C3 H3 O4 0.93 2.58 3.296(3) 134.5 2_656
N2 H2A O9 0.80(3) 2.36(3) 3.120(3) 160(3) .
C9 H9 O1 0.93 2.62 3.531(3) 166.6 2_765
C9 H9 O2 0.93 2.66 3.359(3) 132.3 1_655
C19 H19 Br2 0.93 3.06 3.987(2) 171.4 2_765
O1 H1 O2 0.906(17) 1.715(17) 2.621(2) 178(3) 2_665
C22 H22 Br1 0.93 3.01 3.899(2) 160.4 2_756
O7 H7 O8 0.895(17) 1.703(17) 2.596(2) 176(3) 2_657

_refine_diff_density_max         0.878
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.077


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
