# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Abourahma, Heba'
'Cocuzza, Devon'

_publ_contact_author_name        'Dr Heba Abourahma'
_publ_contact_author_address     
;
Department of Chemistry
2000 Pennington Rd.
Ewing, NJ 08628
United States of America
;
_publ_contact_author_email       abourahm@tcnj.edu
_publ_contact_author_phone       609-771-3302
_publ_section_title              
;
Non-Polymorphic Cocrystals
from Polymorphic Components

;

# Attachment '- Abourahma cif.txt'

#TrackingRef '- Abourahma cif.txt'

_audit_creation_method           'APEX2 v2010.1-2'

_publ_requested_journal          CrystEngComm

data_I
_database_code_depnum_ccdc_archive 'CCDC 826693'
#TrackingRef '- Abourahma cif.txt'

_audit_creation_method           'APEX2 v2010.1-2'

_chemical_name_systematic        '2-Aminobenzoic acid Pyrazinecarboxamide'
_chemical_name_common            'Anthranilic acid Pyrazinamide'
_chemical_formula_moiety         'C7 H7 N O2, C5 H5 N3 O'
_chemical_formula_sum            'C12 H12 N4 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         260.26

_chemical_melting_point          129.4-130.5

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2482(10)
_cell_length_b                   7.5827(10)
_cell_length_c                   12.2794(16)
_cell_angle_alpha                77.826(2)
_cell_angle_beta                 84.096(2)
_cell_angle_gamma                63.018(2)
_cell_volume                     587.88(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    106
_cell_measurement_theta_min      3.1585
_cell_measurement_theta_max      28.3384
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272.0

_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       '\w and \f'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            6960
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             2742
_reflns_number_gt                1742
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1338
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.031
_refine_ls_number_reflns         2742
_refine_ls_number_parameters     173
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.0521P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2010, 1, 0, 0'
_computing_cell_refinement       'APEX2 v2010.1-2 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 v2010.1-2 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.96574(19) -0.02055(18) 0.65313(10) 0.0199(3) Uani d . 1 . .
O O2 0.2816(2) 0.23647(19) 0.51856(10) 0.0232(3) Uani d . 1 . .
H H1 0.3656 0.1718 0.4725 0.035 Uiso calc R 1 . .
O O3 0.47472(19) -0.04211(18) 0.63764(10) 0.0181(3) Uani d . 1 . .
N N1 0.5274(2) 0.4473(2) 0.66892(12) 0.0146(3) Uani d . 1 . .
N N2 0.7793(2) 0.2314(2) 0.51489(12) 0.0210(4) Uani d D 1 . .
H H2A 0.8578 0.1692 0.4622 0.025 Uiso calc RD 1 . .
H H2B 0.6734 0.3505 0.4971 0.025 Uiso calc RD 1 . .
N N3 0.5893(2) 0.2778(2) 0.89685(12) 0.0186(4) Uani d . 1 . .
N N4 0.3782(2) -0.0525(2) 0.85782(13) 0.0235(4) Uani d D 1 . .
H H3A 0.3913 -0.1051 0.9293 0.028 Uiso calc RD 1 . .
H H3B 0.4595 -0.124 0.809 0.028 Uiso calc RD 1 . .
C C1 0.4415(3) 0.4621(3) 0.86016(15) 0.0174(4) Uani d . 1 . .
H H4 0.3548 0.539 0.9132 0.021 Uiso calc R 1 . .
C C2 0.4091(3) 0.5467(3) 0.74742(15) 0.0161(4) Uani d . 1 . .
H H5A 0.3003 0.6781 0.7259 0.019 Uiso calc R 1 . .
C C3 0.6786(3) 0.2641(3) 0.70530(14) 0.0146(4) Uani d . 1 . .
C C4 0.8206(3) 0.1456(3) 0.62111(14) 0.0144(4) Uani d . 1 . .
C C5 0.7091(3) 0.1794(3) 0.81762(15) 0.0175(4) Uani d . 1 . .
H H6 0.8178 0.048 0.8391 0.021 Uiso calc R 1 . .
C C6 0.3308(3) 0.1294(3) 0.62058(14) 0.0153(4) Uani d . 1 . .
C C7 0.2022(3) 0.2346(3) 0.70911(14) 0.0144(4) Uani d . 1 . .
C C8 0.0502(3) 0.4339(3) 0.67997(15) 0.0165(4) Uani d . 1 . .
H H7 0.0316 0.4966 0.6036 0.02 Uiso calc R 1 . .
C C9 -0.0729(3) 0.5415(3) 0.75934(15) 0.0188(4) Uani d . 1 . .
H H8 -0.1748 0.6766 0.7384 0.023 Uiso calc R 1 . .
C C10 -0.0444(3) 0.4469(3) 0.87109(15) 0.0196(4) Uani d . 1 . .
H H9 -0.1284 0.5188 0.9266 0.024 Uiso calc R 1 . .
C C11 0.2324(3) 0.1391(3) 0.82273(14) 0.0158(4) Uani d . 1 . .
C C12 0.1031(3) 0.2519(3) 0.90218(15) 0.0192(4) Uani d . 1 . .
H H10 0.1185 0.1915 0.9789 0.023 Uiso calc R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0198(7) 0.0159(7) 0.0174(7) -0.0023(6) 0.0000(5) -0.0034(5)
O2 0.0225(8) 0.0217(7) 0.0123(7) 0.0007(6) 0.0027(5) -0.0030(5)
O3 0.0186(7) 0.0155(7) 0.0142(6) -0.0027(6) 0.0001(5) -0.0021(5)
N1 0.0141(8) 0.0141(8) 0.0156(8) -0.0058(6) 0.0000(6) -0.0038(6)
N2 0.0200(9) 0.0169(8) 0.0147(8) 0.0017(7) 0.0016(6) -0.0037(6)
N3 0.0194(8) 0.0196(8) 0.0163(8) -0.0084(7) 0.0009(6) -0.0034(6)
N4 0.0320(10) 0.0168(8) 0.0127(8) -0.0032(7) 0.0017(7) -0.0032(6)
C1 0.0163(10) 0.0205(10) 0.0174(9) -0.0089(8) 0.0031(7) -0.0073(8)
C2 0.0156(9) 0.0138(9) 0.0191(9) -0.0065(8) 0.0000(7) -0.0038(7)
C3 0.0144(9) 0.0142(9) 0.0154(9) -0.0065(8) 0.0004(7) -0.0035(7)
C4 0.0139(9) 0.0134(9) 0.0157(9) -0.0053(8) -0.0005(7) -0.0040(7)
C5 0.0172(10) 0.0174(9) 0.0169(9) -0.0070(8) -0.0004(7) -0.0025(7)
C6 0.0150(9) 0.0171(9) 0.0135(9) -0.0069(8) -0.0003(7) -0.0027(7)
C7 0.0145(9) 0.0178(9) 0.0132(9) -0.0088(8) 0.0015(7) -0.0046(7)
C8 0.0165(9) 0.0166(9) 0.0160(9) -0.0077(8) -0.0007(7) -0.0013(7)
C9 0.0144(9) 0.0167(9) 0.0238(10) -0.0050(8) -0.0007(7) -0.0053(8)
C10 0.0194(10) 0.0246(10) 0.0186(9) -0.0112(9) 0.0050(8) -0.0105(8)
C11 0.0183(9) 0.0154(9) 0.0149(9) -0.0083(8) -0.0012(7) -0.0025(7)
C12 0.0239(11) 0.0222(10) 0.0124(9) -0.0114(9) 0.0013(7) -0.0032(7)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.234(2) ?
O2 C6 . 1.325(2) ?
O2 H1 . 0.84 ?
O3 C6 . 1.234(2) ?
N1 C2 . 1.335(2) ?
N1 C3 . 1.337(2) ?
N2 C4 . 1.327(2) ?
N2 H2A . 0.88 ?
N2 H2B . 0.88 ?
N3 C1 . 1.334(2) ?
N3 C5 . 1.342(2) ?
N4 C11 . 1.360(2) ?
N4 H3A . 0.88 ?
N4 H3B . 0.88 ?
C1 C2 . 1.392(2) ?
C1 H4 . 0.95 ?
C2 H5A . 0.95 ?
C3 C5 . 1.387(2) ?
C3 C4 . 1.506(2) ?
C5 H6 . 0.95 ?
C6 C7 . 1.473(2) ?
C7 C8 . 1.403(2) ?
C7 C11 . 1.418(2) ?
C8 C9 . 1.381(2) ?
C8 H7 . 0.95 ?
C9 C10 . 1.396(3) ?
C9 H8 . 0.95 ?
C10 C12 . 1.373(3) ?
C10 H9 . 0.95 ?
C11 C12 . 1.414(2) ?
C12 H10 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 O2 H1 . . 109.5 ?
C2 N1 C3 . . 116.02(15) ?
C4 N2 H2A . . 120.0 ?
C4 N2 H2B . . 120.0 ?
H2A N2 H2B . . 120.0 ?
C1 N3 C5 . . 115.48(16) ?
C11 N4 H3A . . 120.0 ?
C11 N4 H3B . . 120.0 ?
H3A N4 H3B . . 120.0 ?
N3 C1 C2 . . 122.80(16) ?
N3 C1 H4 . . 118.6 ?
C2 C1 H4 . . 118.6 ?
N1 C2 C1 . . 121.44(16) ?
N1 C2 H5A . . 119.3 ?
C1 C2 H5A . . 119.3 ?
N1 C3 C5 . . 122.36(16) ?
N1 C3 C4 . . 118.71(15) ?
C5 C3 C4 . . 118.93(15) ?
O1 C4 N2 . . 124.14(16) ?
O1 C4 C3 . . 119.71(15) ?
N2 C4 C3 . . 116.16(15) ?
N3 C5 C3 . . 121.87(16) ?
N3 C5 H6 . . 119.1 ?
C3 C5 H6 . . 119.1 ?
O3 C6 O2 . . 121.67(16) ?
O3 C6 C7 . . 124.18(16) ?
O2 C6 C7 . . 114.13(15) ?
C8 C7 C11 . . 119.84(16) ?
C8 C7 C6 . . 119.05(16) ?
C11 C7 C6 . . 121.10(15) ?
C9 C8 C7 . . 121.73(17) ?
C9 C8 H7 . . 119.1 ?
C7 C8 H7 . . 119.1 ?
C8 C9 C10 . . 118.45(17) ?
C8 C9 H8 . . 120.8 ?
C10 C9 H8 . . 120.8 ?
C12 C10 C9 . . 121.16(17) ?
C12 C10 H9 . . 119.4 ?
C9 C10 H9 . . 119.4 ?
N4 C11 C12 . . 119.34(16) ?
N4 C11 C7 . . 123.38(16) ?
C12 C11 C7 . . 117.28(16) ?
C10 C12 C11 . . 121.54(17) ?
C10 C12 H10 . . 119.2 ?
C11 C12 H10 . . 119.2 ?