#------------------------------------------------------------------------------
#$Date: 2016-03-26 23:02:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180527 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/96/7219645.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7219645
loop_
_publ_author_name
'Lemmerer, Andreas'
'Govindraju, Stefan'
'Johnston, Marcelle'
'Motloung, Xolani'
'Savig, Kelsey L.'
_publ_section_title
;
 Co-crystals and molecular salts of carboxylic acid/pyridine complexes:
 can calculated pKa's predict proton transfer? A case study of nine
 complexes
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              3591
_journal_paper_doi               10.1039/C5CE00102A
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C7 H3 Cl N O4, C5 H6 Br N2'
_chemical_formula_sum            'C12 H9 Br Cl N3 O4'
_chemical_formula_weight         374.58
_chemical_name_systematic
;
 (2-chloro-4-nitrobenzoate)(2-amino-3-bromopyridinium)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2012-11-02T08:38:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2014-11-18 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                98.577(2)
_cell_angle_beta                 105.0740(10)
_cell_angle_gamma                98.022(2)
_cell_formula_units_Z            2
_cell_length_a                   6.4350(2)
_cell_length_b                   10.3354(3)
_cell_length_c                   11.2546(4)
_cell_measurement_reflns_used    8156
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.5
_cell_volume                     702.11(4)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'APEX3 (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker 2007)'
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16110
_diffrn_reflns_theta_full        28
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         1.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.136
_exptl_absorpt_correction_T_max  0.7242
_exptl_absorpt_correction_T_min  0.3596
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0389P)²+0.3660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0729
_reflns_number_gt                2950
_reflns_number_total             3389
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce00102a4.cif
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 7219641--7219649.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7219645
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.6183(3) 0.71139(17) 0.20034(15) 0.0239(3) Uani 1 1 d .
C2 C 0.6652(3) 0.84180(18) 0.26517(17) 0.0267(4) Uani 1 1 d .
C3 C 0.8259(3) 0.93669(18) 0.24964(18) 0.0293(4) Uani 1 1 d .
H3 H 0.8568 1.0257 0.2949 0.035 Uiso 1 1 calc R
C4 C 0.9391(3) 0.89751(18) 0.16630(17) 0.0264(4) Uani 1 1 d .
C5 C 0.8958(3) 0.7703(2) 0.09766(18) 0.0303(4) Uani 1 1 d .
H5 H 0.9755 0.7462 0.0402 0.036 Uiso 1 1 calc R
C6 C 0.7328(3) 0.67781(19) 0.11437(17) 0.0290(4) Uani 1 1 d .
H6 H 0.6987 0.5899 0.0663 0.035 Uiso 1 1 calc R
C7 C 0.4591(3) 0.60395(17) 0.22618(16) 0.0259(4) Uani 1 1 d .
N1 N 1.1120(3) 0.99729(18) 0.15070(17) 0.0346(4) Uani 1 1 d .
O1 O 0.5205(2) 0.57150(15) 0.33022(13) 0.0404(4) Uani 1 1 d .
O2 O 0.2845(2) 0.55416(14) 0.14195(12) 0.0323(3) Uani 1 1 d .
O3 O 1.1406(3) 1.11131(16) 0.20832(18) 0.0493(4) Uani 1 1 d .
O4 O 1.2185(3) 0.96137(18) 0.08073(16) 0.0478(4) Uani 1 1 d .
Cl1 Cl 0.52379(10) 0.89101(6) 0.37043(6) 0.04732(15) Uani 1 1 d .
C8 C 0.0354(3) 0.36877(17) 0.33914(16) 0.0248(3) Uani 1 1 d .
C9 C -0.1395(3) 0.29647(18) 0.37164(17) 0.0268(4) Uani 1 1 d .
C10 C -0.3384(3) 0.2513(2) 0.2861(2) 0.0339(4) Uani 1 1 d .
H10 H -0.4543 0.2038 0.3093 0.041 Uiso 1 1 calc R
C11 C -0.3730(3) 0.2748(2) 0.1631(2) 0.0375(5) Uani 1 1 d .
H11 H -0.5101 0.2409 0.1017 0.045 Uiso 1 1 calc R
C12 C -0.2067(3) 0.34685(19) 0.13399(17) 0.0303(4) Uani 1 1 d .
H12 H -0.2281 0.3647 0.0517 0.036 Uiso 1 1 calc R
N2 N -0.0100(3) 0.39376(15) 0.22144(14) 0.0259(3) Uani 1 1 d .
H2 H 0.083(4) 0.442(3) 0.202(2) 0.046(7) Uiso 1 1 d .
N3 N 0.2346(3) 0.41177(18) 0.41611(16) 0.0355(4) Uani 1 1 d .
H3A H 0.328(4) 0.459(2) 0.393(2) 0.035(6) Uiso 1 1 d .
H3B H 0.268(4) 0.396(2) 0.492(3) 0.043(7) Uiso 1 1 d .
Br1 Br -0.08488(3) 0.26143(2) 0.534354(18) 0.04094(9) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -2 1 0.144
0 1 0 0.053
0 -1 0 0.044
-2 1 1 0.129
2 -1 -1 0.203
1 0 -2 0.196
0 1 -2 0.184
1 -1 2 0.146
0 0 1 0.148
-1 1 -2 0.132
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 118.01(16)
C2 C1 C7 122.24(16)
C6 C1 C7 119.62(16)
C1 C2 C3 121.97(17)
C1 C2 Cl1 120.30(14)
C3 C2 Cl1 117.73(14)
C4 C3 C2 117.77(17)
C4 C3 H3 121.1
C2 C3 H3 121.1
C5 C4 C3 122.62(17)
C5 C4 N1 119.33(17)
C3 C4 N1 118.05(17)
C4 C5 C6 118.30(17)
C4 C5 H5 120.9
C6 C5 H5 120.9
C5 C6 C1 121.28(17)
C5 C6 H6 119.4
C1 C6 H6 119.4
O1 C7 O2 126.32(16)
O1 C7 C1 115.44(15)
O2 C7 C1 118.21(15)
O4 N1 O3 123.74(17)
O4 N1 C4 118.12(17)
O3 N1 C4 118.13(17)
N3 C8 N2 119.31(17)
N3 C8 C9 124.09(16)
N2 C8 C9 116.61(16)
C10 C9 C8 120.86(17)
C10 C9 Br1 121.08(14)
C8 C9 Br1 118.05(13)
C9 C10 C11 120.00(18)
C9 C10 H10 120
C11 C10 H10 120
C12 C11 C10 118.65(18)
C12 C11 H11 120.7
C10 C11 H11 120.7
C11 C12 N2 120.60(17)
C11 C12 H12 119.7
N2 C12 H12 119.7
C8 N2 C12 123.18(16)
C8 N2 H2 119.1(19)
C12 N2 H2 117.6(18)
C8 N3 H3A 119.4(16)
C8 N3 H3B 121.1(17)
H3A N3 H3B 119(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.385(3)
C1 C6 1.394(3)
C1 C7 1.517(2)
C2 C3 1.387(2)
C2 Cl1 1.7322(18)
C3 C4 1.378(3)
C3 H3 0.95
C4 C5 1.373(3)
C4 N1 1.473(2)
C5 C6 1.388(3)
C5 H5 0.95
C6 H6 0.95
C7 O1 1.246(2)
C7 O2 1.251(2)
N1 O4 1.222(2)
N1 O3 1.222(2)
C8 N3 1.319(2)
C8 N2 1.352(2)
C8 C9 1.421(2)
C9 C10 1.357(3)
C9 Br1 1.8727(18)
C10 C11 1.407(3)
C10 H10 0.95
C11 C12 1.356(3)
C11 H11 0.95
C12 N2 1.358(2)
C12 H12 0.95
N2 H2 0.82(3)
N3 H3A 0.84(3)
N3 H3B 0.87(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.82(3) 1.93(3) 2.754(2) 175(3) .
N3 H3A O1 0.84(3) 1.92(3) 2.757(2) 175(2) .
N3 H3B O1 0.87(3) 2.05(3) 2.846(2) 151(2) 2_666
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
C6 C1 C2 C3 -2.1(3)
C7 C1 C2 C3 173.79(17)
C6 C1 C2 Cl1 178.36(14)
C7 C1 C2 Cl1 -5.7(2)
C1 C2 C3 C4 0.2(3)
Cl1 C2 C3 C4 179.75(14)
C2 C3 C4 C5 1.2(3)
C2 C3 C4 N1 -179.14(17)
C3 C4 C5 C6 -0.6(3)
N1 C4 C5 C6 179.70(17)
C4 C5 C6 C1 -1.4(3)
C2 C1 C6 C5 2.7(3)
C7 C1 C6 C5 -173.33(17)
C2 C1 C7 O1 -68.1(2)
C6 C1 C7 O1 107.7(2)
C2 C1 C7 O2 113.8(2)
C6 C1 C7 O2 -70.4(2)
C5 C4 N1 O4 -3.3(3)
C3 C4 N1 O4 177.07(18)
C5 C4 N1 O3 176.63(18)
C3 C4 N1 O3 -3.0(3)
N3 C8 C9 C10 -177.7(2)
N2 C8 C9 C10 2.4(3)
N3 C8 C9 Br1 0.6(3)
N2 C8 C9 Br1 -179.27(13)
C8 C9 C10 C11 0.6(3)
Br1 C9 C10 C11 -177.69(16)
C9 C10 C11 C12 -2.3(3)
C10 C11 C12 N2 0.9(3)
N3 C8 N2 C12 176.18(19)
C9 C8 N2 C12 -3.9(3)
C11 C12 N2 C8 2.3(3)
