# Electronic Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_asanik
#TrackingRef '19300_web_deposit_cif_file_0_IneseSarcevica_1365510577.4aminosalicylicacid-nicotinamide-cocrystal.cif'


_audit_update_record             
;
2012-12-05 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            
'4-aminosalicylic acid - nicotinamide cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 N O3, C6 H6 N2 O'
_chemical_formula_sum            'C13 H13 N3 O4'
_chemical_formula_weight         275.26

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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'

_cell_length_a                   4.58580(10)
_cell_length_b                   12.6009(2)
_cell_length_c                   21.2600(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.0440(7)
_cell_angle_gamma                90.00
_cell_volume                     1225.45(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    17849
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.878

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5175
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         27.88
_reflns_number_total             2900
_reflns_number_gt                2368
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+0.4172P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2900
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.1097(2) 0.33406(9) 0.02941(5) 0.0241(2) Uani 1 1 d . . .
C2 C -0.3023(3) 0.25669(10) 0.03848(6) 0.0219(3) Uani 1 1 d . . .
H2 H -0.3278 0.2349 0.0795 0.026 Uiso 1 1 calc R . .
C3 C -0.4661(3) 0.20739(10) -0.01073(6) 0.0203(3) Uani 1 1 d . . .
C4 C -0.4214(3) 0.23953(11) -0.07187(6) 0.0244(3) Uani 1 1 d . . .
H4 H -0.5245 0.2075 -0.1060 0.029 Uiso 1 1 calc R . .
C5 C -0.2230(3) 0.31933(11) -0.08164(6) 0.0265(3) Uani 1 1 d . . .
H5 H -0.1911 0.3420 -0.1222 0.032 Uiso 1 1 calc R . .
C6 C -0.0730(3) 0.36463(11) -0.02978(6) 0.0245(3) Uani 1 1 d . . .
H6 H 0.0594 0.4188 -0.0363 0.029 Uiso 1 1 calc R . .
C7 C -0.6805(3) 0.11944(10) -0.00157(6) 0.0217(3) Uani 1 1 d . . .
O8 O -0.7654(2) 0.06447(8) -0.04744(4) 0.0291(2) Uani 1 1 d . . .
N9 N -0.7712(2) 0.10356(10) 0.05592(5) 0.0248(3) Uani 1 1 d . . .
H9A H -0.908(4) 0.0529(15) 0.0590(8) 0.039(5) Uiso 1 1 d . . .
H9B H -0.744(4) 0.1498(14) 0.0868(8) 0.038(5) Uiso 1 1 d . . .
O10 O 0.2702(2) 0.42306(8) 0.11263(4) 0.0283(2) Uani 1 1 d . . .
H10 H 0.131(5) 0.3848(18) 0.0852(10) 0.070(6) Uiso 1 1 d . . .
O11 O 0.2819(2) 0.27040(8) 0.16645(4) 0.0292(2) Uani 1 1 d . . .
C12 C 0.3663(3) 0.36365(11) 0.16065(6) 0.0221(3) Uani 1 1 d . . .
C13 C 0.5820(3) 0.41384(10) 0.20492(6) 0.0208(3) Uani 1 1 d . . .
C14 C 0.6856(3) 0.36053(10) 0.26031(6) 0.0218(3) Uani 1 1 d . . .
O15 O 0.5822(2) 0.26303(8) 0.27500(5) 0.0294(2) Uani 1 1 d . . .
H15 H 0.443(5) 0.2448(19) 0.2402(11) 0.074(7) Uiso 1 1 d . . .
C16 C 0.8962(3) 0.40614(11) 0.30182(6) 0.0231(3) Uani 1 1 d . . .
H16 H 0.9624 0.3698 0.3381 0.028 Uiso 1 1 calc R . .
C17 C 1.0092(3) 0.50599(11) 0.28957(6) 0.0221(3) Uani 1 1 d . . .
N20 N 1.2152(3) 0.55242(11) 0.33063(6) 0.0280(3) Uani 1 1 d . . .
H20A H 1.299(4) 0.5108(16) 0.3624(9) 0.047(5) Uiso 1 1 d . . .
H20B H 1.311(4) 0.6029(15) 0.3174(8) 0.039(5) Uiso 1 1 d . . .
C18 C 0.9030(3) 0.56113(11) 0.23483(6) 0.0238(3) Uani 1 1 d . . .
H18 H 0.9734 0.6285 0.2265 0.029 Uiso 1 1 calc R . .
C19 C 0.6956(3) 0.51492(11) 0.19396(6) 0.0236(3) Uani 1 1 d . . .
H19 H 0.6283 0.5518 0.1579 0.028 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0247(5) 0.0245(6) 0.0225(5) -0.0028(4) -0.0020(4) -0.0009(4)
C2 0.0231(6) 0.0240(7) 0.0184(6) -0.0001(5) 0.0000(5) 0.0014(5)
C3 0.0187(5) 0.0214(6) 0.0207(6) -0.0015(5) -0.0001(5) 0.0041(5)
C4 0.0252(6) 0.0277(7) 0.0196(6) -0.0028(5) -0.0030(5) 0.0003(5)
C5 0.0294(7) 0.0293(7) 0.0207(6) 0.0024(5) 0.0016(5) -0.0002(6)
C6 0.0249(6) 0.0221(7) 0.0264(7) 0.0007(5) 0.0009(5) -0.0002(5)
C7 0.0197(6) 0.0227(7) 0.0222(6) -0.0016(5) -0.0018(5) 0.0033(5)
O8 0.0317(5) 0.0306(5) 0.0249(5) -0.0070(4) 0.0004(4) -0.0067(4)
N9 0.0266(6) 0.0248(6) 0.0232(6) -0.0016(5) 0.0027(5) -0.0030(5)
O10 0.0337(5) 0.0266(5) 0.0229(5) 0.0010(4) -0.0095(4) -0.0049(4)
O11 0.0381(5) 0.0250(5) 0.0239(5) -0.0010(4) -0.0008(4) -0.0074(4)
C12 0.0246(6) 0.0245(7) 0.0174(6) -0.0023(5) 0.0029(5) 0.0006(5)
C13 0.0218(6) 0.0221(7) 0.0185(6) -0.0012(5) 0.0010(5) 0.0008(5)
C14 0.0233(6) 0.0206(6) 0.0218(6) 0.0001(5) 0.0037(5) 0.0025(5)
O15 0.0376(5) 0.0223(5) 0.0275(5) 0.0046(4) -0.0032(4) -0.0027(4)
C16 0.0244(6) 0.0263(7) 0.0182(6) 0.0013(5) -0.0014(5) 0.0045(5)
C17 0.0199(6) 0.0272(7) 0.0192(6) -0.0034(5) 0.0022(5) 0.0014(5)
N20 0.0281(6) 0.0330(7) 0.0222(6) 0.0000(5) -0.0034(5) -0.0057(5)
C18 0.0263(6) 0.0231(7) 0.0221(6) 0.0007(5) 0.0017(5) -0.0037(5)
C19 0.0265(6) 0.0255(7) 0.0187(6) 0.0027(5) -0.0006(5) 0.0008(5)

_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
N1 C6 1.3381(17) . ?
N1 C2 1.3384(17) . ?
C2 C3 1.3905(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.3905(18) . ?
C3 C7 1.5034(18) . ?
C4 C5 1.3816(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.3811(18) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O8 1.2363(15) . ?
C7 N9 1.3336(17) . ?
N9 H9A 0.899(19) . ?
N9 H9B 0.880(18) . ?
O10 C12 1.3165(15) . ?
O10 H10 0.96(2) . ?
O11 C12 1.2459(16) . ?
C12 C13 1.4607(17) . ?
C13 C19 1.4017(18) . ?
C13 C14 1.4088(17) . ?
C14 O15 1.3612(16) . ?
C14 C16 1.3862(17) . ?
O15 H15 0.97(2) . ?
C16 C17 1.3924(19) . ?
C16 H16 0.9300 . ?
C17 N20 1.3710(16) . ?
C17 C18 1.4123(18) . ?
N20 H20A 0.917(19) . ?
N20 H20B 0.832(19) . ?
C18 C19 1.3719(18) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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 N1 C2 118.25(11) . . ?
N1 C2 C3 122.95(12) . . ?
N1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C2 C3 C4 117.77(12) . . ?
C2 C3 C7 123.74(12) . . ?
C4 C3 C7 118.46(11) . . ?
C5 C4 C3 119.64(12) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 118.49(12) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
N1 C6 C5 122.90(13) . . ?
N1 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
O8 C7 N9 122.52(12) . . ?
O8 C7 C3 118.90(12) . . ?
N9 C7 C3 118.58(11) . . ?
C7 N9 H9A 115.9(11) . . ?
C7 N9 H9B 123.2(11) . . ?
H9A N9 H9B 118.5(16) . . ?
C12 O10 H10 110.9(13) . . ?
O11 C12 O10 121.59(11) . . ?
O11 C12 C13 123.05(11) . . ?
O10 C12 C13 115.34(12) . . ?
C19 C13 C14 117.70(11) . . ?
C19 C13 C12 121.94(11) . . ?
C14 C13 C12 120.35(12) . . ?
O15 C14 C16 117.81(11) . . ?
O15 C14 C13 121.32(11) . . ?
C16 C14 C13 120.88(12) . . ?
C14 O15 H15 105.0(14) . . ?
C14 C16 C17 120.49(11) . . ?
C14 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
N20 C17 C16 121.03(12) . . ?
N20 C17 C18 119.79(13) . . ?
C16 C17 C18 119.16(11) . . ?
C17 N20 H20A 117.2(12) . . ?
C17 N20 H20B 117.8(12) . . ?
H20A N20 H20B 118.9(17) . . ?
C19 C18 C17 119.78(12) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C13 121.97(12) . . ?
C18 C19 H19 119.0 . . ?
C13 C19 H19 119.0 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042


_database_code_depnum_ccdc_archive 'CCDC 933429'