#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:07:04 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180412 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/81/7208173.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_7208173
loop_
_publ_author_name
'Chiya, Thabang J.'
'Lemmerer, Andreas'
_publ_section_title
;
 Stoichiometric variation in two molecular salts of the anti-tuberculosis
 drug isoniazid with 2-butynoic acid
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              5124
_journal_paper_doi               10.1039/c2ce25101a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C6 H9 N3 O, 2(C4 H3 O2)'
_chemical_formula_sum            'C14 H15 N3 O5'
_chemical_formula_weight         305.29
_chemical_name_systematic
;
(4-(diazan-2-ium-1-ylcarbonyl)pyridinium)?(but-2-yn-1-olate)2
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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             2011-12-26T11:53:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.8587(7)
_cell_length_b                   13.6008(15)
_cell_length_c                   31.175(3)
_cell_measurement_reflns_used    2099
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      3
_cell_volume                     2908.1(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1482
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            21420
_diffrn_reflns_theta_full        28
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         2.61
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1283
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0806P)²+0.1668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1724
_reflns_number_gt                1911
_reflns_number_total             3448
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25101a.txt
_cod_data_source_block           11a_d3_p
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group_crystal_system' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               7208173
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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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 0.1433(4) 0.79498(18) 0.23541(8) 0.0260(6) Uani 1 1 d .
C2 C 0.1405(4) 0.69558(19) 0.22513(9) 0.0295(6) Uani 1 1 d .
H2A H 0.141 0.6746 0.1961 0.035 Uiso 1 1 calc R
C3 C 0.1371(4) 0.62782(19) 0.25827(10) 0.0339(7) Uani 1 1 d .
H3 H 0.1351 0.5595 0.2518 0.041 Uiso 1 1 calc R
C4 C 0.1382(4) 0.7529(2) 0.30962(10) 0.0327(6) Uani 1 1 d .
H4 H 0.1375 0.7716 0.339 0.039 Uiso 1 1 calc R
C5 C 0.1410(4) 0.82381(19) 0.27829(9) 0.0299(6) Uani 1 1 d .
H5 H 0.1413 0.8915 0.2857 0.036 Uiso 1 1 calc R
C6 C 0.1499(4) 0.87688(19) 0.20245(9) 0.0268(6) Uani 1 1 d .
N1 N 0.1798(3) 0.84838(17) 0.16228(7) 0.0292(5) Uani 1 1 d .
H1 H 0.208(6) 0.785(3) 0.1524(13) 0.083(14) Uiso 1 1 d .
N2 N 0.1365(3) 0.65709(17) 0.29900(8) 0.0305(5) Uani 1 1 d .
H2 H 0.149(5) 0.601(3) 0.3224(12) 0.070(11) Uiso 1 1 d .
N3 N 0.1932(4) 0.92345(16) 0.13049(8) 0.0291(5) Uani 1 1 d .
H3A H 0.321(5) 0.959(2) 0.1363(10) 0.044(9) Uiso 1 1 d .
H3B H 0.076(6) 0.965(3) 0.1326(12) 0.059(10) Uiso 1 1 d .
H3C H 0.207(5) 0.894(3) 0.1040(11) 0.057(11) Uiso 1 1 d .
O1 O 0.1256(3) 0.96261(13) 0.21339(6) 0.0365(5) Uani 1 1 d .
C7 C 0.3114(4) 0.49082(19) 0.36751(9) 0.0293(6) Uani 1 1 d .
C8 C 0.3124(4) 0.4113(2) 0.39909(9) 0.0324(6) Uani 1 1 d .
C9 C 0.3063(4) 0.3428(2) 0.42297(10) 0.0356(7) Uani 1 1 d .
C10 C 0.2940(5) 0.2585(2) 0.45190(11) 0.0496(9) Uani 1 1 d .
H10A H 0.1647 0.2567 0.4653 0.074 Uiso 1 1 calc R
H10B H 0.394 0.2644 0.4742 0.074 Uiso 1 1 calc R
H10C H 0.3152 0.1978 0.4356 0.074 Uiso 1 1 calc R
O2 O 0.1472(3) 0.53202(14) 0.36179(7) 0.0362(5) Uani 1 1 d .
O3 O 0.4628(3) 0.51175(16) 0.34756(7) 0.0406(5) Uani 1 1 d .
C11 C 0.2402(4) 0.6947(2) 0.08763(10) 0.0316(6) Uani 1 1 d .
C12 C 0.2459(4) 0.6074(2) 0.06026(9) 0.0365(7) Uani 1 1 d .
C13 C 0.2489(5) 0.5389(2) 0.03637(10) 0.0397(7) Uani 1 1 d .
C14 C 0.2517(6) 0.4556(2) 0.00689(11) 0.0531(10) Uani 1 1 d .
H14A H 0.1289 0.4191 0.0093 0.08 Uiso 1 1 calc R
H14B H 0.3608 0.4121 0.0142 0.08 Uiso 1 1 calc R
H14C H 0.2675 0.4795 -0.0226 0.08 Uiso 1 1 calc R
O4 O 0.1932(3) 0.77420(15) 0.07058(7) 0.0425(6) Uani 1 1 d .
O5 O 0.2828(3) 0.68313(14) 0.12676(6) 0.0392(5) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C5 119.7(2)
C2 C1 C6 124.0(2)
C5 C1 C6 116.3(2)
C3 C2 C1 118.4(3)
C3 C2 H2A 120.8
C1 C2 H2A 120.8
N2 C3 C2 120.9(3)
N2 C3 H3 119.6
C2 C3 H3 119.6
N2 C4 C5 120.4(3)
N2 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C1 119.0(2)
C4 C5 H5 120.5
C1 C5 H5 120.5
O1 C6 N1 124.1(2)
O1 C6 C1 120.4(2)
N1 C6 C1 115.4(2)
C6 N1 N3 117.2(2)
C6 N1 H1 128(3)
N3 N1 H1 115(3)
C3 N2 C4 121.7(2)
C3 N2 H2 116(2)
C4 N2 H2 122(2)
N1 N3 H3A 105.9(18)
N1 N3 H3B 108(2)
H3A N3 H3B 114(3)
N1 N3 H3C 109(2)
H3A N3 H3C 106(3)
H3B N3 H3C 113(3)
O3 C7 O2 124.7(3)
O3 C7 C8 120.1(2)
O2 C7 C8 115.1(2)
C9 C8 C7 175.6(3)
C8 C9 C10 178.7(4)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O4 C11 O5 125.4(3)
O4 C11 C12 117.5(3)
O5 C11 C12 117.1(2)
C13 C12 C11 177.0(3)
C12 C13 C14 179.6(4)
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.389(4)
C1 C5 1.393(4)
C1 C6 1.516(4)
C2 C3 1.385(4)
C2 H2A 0.95
C3 N2 1.331(4)
C3 H3 0.95
C4 N2 1.344(4)
C4 C5 1.373(4)
C4 H4 0.95
C5 H5 0.95
C6 O1 1.226(3)
C6 N1 1.327(3)
N1 N3 1.426(3)
N1 H1 0.93(5)
N2 H2 1.06(4)
N3 H3A 1.02(3)
N3 H3B 0.99(4)
N3 H3C 0.92(4)
C7 O3 1.243(3)
C7 O2 1.270(3)
C7 C8 1.463(4)
C8 C9 1.193(4)
C9 C10 1.461(4)
C10 H10A 0.98
C10 H10B 0.98
C10 H10C 0.98
C11 O4 1.247(3)
C11 O5 1.264(3)
C11 C12 1.462(4)
C12 C13 1.193(4)
C13 C14 1.460(4)
C14 H14A 0.98
C14 H14B 0.98
C14 H14C 0.98
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 H1 O5 0.93(5) 1.68(5) 2.603(3) 168(4) .
N2 H2 O2 1.06(4) 1.54(4) 2.594(3) 170(3) .
N3 H3A O3 1.02(3) 1.72(3) 2.734(3) 173(3) 3_655
N3 H3B O2 0.99(4) 1.79(4) 2.773(3) 175(3) 3
N3 H3C O4 0.92(4) 1.94(4) 2.758(3) 147(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 C1 C2 C3 -0.5(4)
C6 C1 C2 C3 179.1(2)
C1 C2 C3 N2 0.0(4)
N2 C4 C5 C1 -0.4(4)
C2 C1 C5 C4 0.7(4)
C6 C1 C5 C4 -179.0(2)
C2 C1 C6 O1 170.1(3)
C5 C1 C6 O1 -10.2(4)
C2 C1 C6 N1 -8.8(4)
C5 C1 C6 N1 170.8(2)
O1 C6 N1 N3 3.1(4)
C1 C6 N1 N3 -178.0(2)
C2 C3 N2 C4 0.4(4)
C5 C4 N2 C3 -0.1(4)
