#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:44:50 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179672 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/25/4512559.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_4512559
loop_
_publ_author_name
'Prasad, Karothu Durga'
'Cherukuvada, Suryanarayan'
'Ganduri, Ramesh'
'Stephen, L. Devaraj'
'Perumalla, Sravankumar'
'Guru Row, Tayur N.'
_publ_section_title
;
 Differential Cocrystallization Behavior of Isomeric Pyridine Carboxamides
 toward Antitubercular Drug Pyrazinoic Acid
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              858
_journal_paper_doi               10.1021/cg501642m
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C9 H11 N5 O4'
_chemical_formula_weight         253.23
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.938(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2384(9)
_cell_length_b                   28.141(5)
_cell_length_c                   7.8234(13)
_cell_measurement_temperature    298(2)
_cell_volume                     1152.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9854
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9769
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.047
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0737P)²+0.2331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1547
_reflns_number_gt                1716
_reflns_number_total             2272
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            POA_CYT_Hydrate.cif
_cod_data_source_block           POA_CYT_Hydrate
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/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 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4512557--4512561.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4512559
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C -0.1123(4) 0.61845(8) 0.4111(3) 0.0466(5) Uani 1 1 d
C2 C -0.3296(4) 0.59881(7) 0.2997(3) 0.0443(5) Uani 1 1 d
C3 C -0.6668(4) 0.61217(9) 0.1144(3) 0.0546(6) Uani 1 1 d
H3 H -0.764(6) 0.6359(10) 0.050(4) 0.080(9) Uiso 1 1 d
C4 C -0.7150(5) 0.56394(9) 0.1067(3) 0.0580(6) Uani 1 1 d
H4A H -0.863(5) 0.5525(9) 0.037(3) 0.064(7) Uiso 1 1 d
C5 C -0.3807(5) 0.55050(9) 0.2915(3) 0.0569(6) Uani 1 1 d
H5A H -0.272(6) 0.5267(10) 0.357(4) 0.082(9) Uiso 1 1 d
C6 C 0.4721(4) 0.67073(7) 0.6939(3) 0.0420(5) Uani 1 1 d
C7 C 0.3356(4) 0.75023(8) 0.6128(3) 0.0436(5) Uani 1 1 d
C8 C 0.7104(4) 0.73771(8) 0.7905(3) 0.0459(5) Uani 1 1 d
H8 H 0.853(4) 0.7533(8) 0.857(3) 0.057(6) Uiso 1 1 d
C9 C 0.6838(4) 0.69053(8) 0.7884(3) 0.0462(5) Uani 1 1 d
H9 H 0.799(5) 0.6704(8) 0.842(3) 0.054(7) Uiso 1 1 d
N1 N -0.4745(3) 0.62994(6) 0.2102(2) 0.0480(5) Uani 1 1 d
N2 N -0.5735(4) 0.53265(7) 0.1952(3) 0.0610(6) Uani 1 1 d
N3 N 0.4254(4) 0.62495(7) 0.6852(3) 0.0515(5) Uani 1 1 d
H3A H 0.550(5) 0.6043(10) 0.741(4) 0.068(8) Uiso 1 1 d
H3B H 0.291(6) 0.6136(10) 0.612(4) 0.074(8) Uiso 1 1 d
N4 N 0.3126(3) 0.70128(6) 0.6093(2) 0.0419(4) Uani 1 1 d
H4 H 0.179(5) 0.6885(9) 0.538(4) 0.068(8) Uiso 1 1 d
N5 N 0.5413(3) 0.76718(7) 0.7074(2) 0.0450(5) Uani 1 1 d
H5 H 0.560(4) 0.8019(9) 0.713(3) 0.056(7) Uiso 1 1 d
O1 O -0.0771(3) 0.66223(6) 0.4102(2) 0.0562(5) Uani 1 1 d
O2 O 0.0136(3) 0.58817(6) 0.4977(2) 0.0621(5) Uani 1 1 d
O3 O 0.1847(3) 0.77594(5) 0.5353(2) 0.0562(5) Uani 1 1 d
O4 O 0.8016(4) 0.55929(7) 0.8082(3) 0.0684(6) Uani 1 1 d
H4B H 0.892(7) 0.5619(13) 0.704(5) 0.118(14) Uiso 1 1 d
H4C H 0.723(6) 0.5287(13) 0.810(4) 0.097(11) Uiso 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 0.0000 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 O2 126.6(2)
O1 C1 C2 117.76(19)
O2 C1 C2 115.60(19)
N1 C2 C5 120.8(2)
N1 C2 C1 117.59(18)
C5 C2 C1 121.6(2)
N1 C3 C4 121.8(2)
N2 C4 C3 122.0(2)
N2 C5 C2 122.3(2)
N3 C6 N4 119.10(19)
N3 C6 C9 123.4(2)
N4 C6 C9 117.48(19)
O3 C7 N5 123.1(2)
O3 C7 N4 121.82(18)
N5 C7 N4 115.04(18)
C9 C8 N5 122.2(2)
C8 C9 C6 118.3(2)
C3 N1 C2 116.9(2)
C4 N2 C5 116.2(2)
C6 N4 C7 124.76(17)
C8 N5 C7 122.13(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.246(3)
C1 O2 1.261(3)
C1 C2 1.515(3)
C2 N1 1.341(3)
C2 C5 1.387(3)
C3 N1 1.333(3)
C3 C4 1.381(3)
C4 N2 1.330(3)
C5 N2 1.337(3)
C6 N3 1.313(3)
C6 N4 1.356(3)
C6 C9 1.425(3)
C7 O3 1.218(2)
C7 N5 1.372(3)
C7 N4 1.383(3)
C8 C9 1.335(3)
C8 N5 1.362(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
O1 C1 C2 N1 -1.6(3)
O2 C1 C2 N1 177.6(2)
O1 C1 C2 C5 179.3(2)
O2 C1 C2 C5 -1.5(3)
N1 C3 C4 N2 0.4(4)
N1 C2 C5 N2 0.2(4)
C1 C2 C5 N2 179.3(2)
N5 C8 C9 C6 0.7(3)
N3 C6 C9 C8 -178.9(2)
N4 C6 C9 C8 1.1(3)
C4 C3 N1 C2 -0.2(3)
C5 C2 N1 C3 -0.1(3)
C1 C2 N1 C3 -179.23(19)
C3 C4 N2 C5 -0.3(4)
C2 C5 N2 C4 0.0(4)
N3 C6 N4 C7 177.69(19)
C9 C6 N4 C7 -2.3(3)
O3 C7 N4 C6 -179.3(2)
N5 C7 N4 C6 1.6(3)
C9 C8 N5 C7 -1.5(3)
O3 C7 N5 C8 -178.8(2)
N4 C7 N5 C8 0.3(3)
