#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:52:43 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179544 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/13/4501327.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_4501327
loop_
_publ_author_name
'Das, Babulal'
'Baruah, Jubaraj B.'
_publ_section_title
;
 Supramolecular Synthons and Hydrates in Stabilization of Multicomponent
 Crystals of Nicotinamide and Isonicotinamide with N-Containing Aromatic
 Dicarboxylic Acids
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5522
_journal_paper_doi               10.1021/cg201096c
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C13 H13 N3 O6'
_chemical_formula_weight         307.26
_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                 93.400(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.7184(3)
_cell_length_b                   13.3383(9)
_cell_length_c                   25.3647(18)
_cell_measurement_reflns_used    4035
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1255.80(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19266
_diffrn_reflns_theta_full        28.47
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin needles'
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1534P)²+0.2321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2191
_refine_ls_wR_factor_ref         0.2350
_reflns_number_gt                2010
_reflns_number_total             3124
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg201096c_si_007.cif
_cod_data_source_block           nico-23pdc-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4501327
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
_atom_site_refinement_flags
C1 C 0.6775(8) 0.39314(19) 0.27023(11) 0.0408(6) Uani 1 1 d .
C2 C 0.7946(7) 0.29867(17) 0.30180(10) 0.0352(6) Uani 1 1 d .
C3 C 1.0492(8) 0.1413(2) 0.28843(12) 0.0464(7) Uani 1 1 d .
H3 H 1.1421 0.0952 0.2653 0.056 Uiso 1 1 calc R
C4 C 1.0396(8) 0.11614(19) 0.34070(12) 0.0468(7) Uani 1 1 d .
H4 H 1.1239 0.0543 0.3531 0.056 Uiso 1 1 calc R
C5 C 0.9014(8) 0.1851(2) 0.37420(12) 0.0444(7) Uani 1 1 d .
H5 H 0.8920 0.1696 0.4098 0.053 Uiso 1 1 calc R
C6 C 0.7742(7) 0.27840(18) 0.35591(10) 0.0363(6) Uani 1 1 d .
C7 C 0.6247(8) 0.3447(2) 0.39873(11) 0.0444(7) Uani 1 1 d .
C8 C 0.3127(8) 0.38660(19) 0.04603(11) 0.0395(6) Uani 1 1 d .
C9 C 0.1887(7) 0.29946(18) 0.07790(10) 0.0362(6) Uani 1 1 d .
C10 C 0.1135(8) 0.2048(2) 0.05791(11) 0.0435(7) Uani 1 1 d .
H10 H 0.1455 0.1912 0.0225 0.052 Uiso 1 1 calc R
C11 C -0.0083(8) 0.1306(2) 0.08997(13) 0.0492(8) Uani 1 1 d .
H11 H -0.0611 0.0672 0.0765 0.059 Uiso 1 1 calc R
C12 C -0.0511(8) 0.1516(2) 0.14228(12) 0.0473(7) Uani 1 1 d .
H12 H -0.1319 0.1018 0.1644 0.057 Uiso 1 1 calc R
C13 C 0.1396(7) 0.3168(2) 0.13074(10) 0.0409(6) Uani 1 1 d .
H13 H 0.1877 0.3799 0.1450 0.049 Uiso 1 1 calc R
H2N H -0.034(10) 0.252(3) 0.1999(16) 0.076(11) Uiso 1 1 d .
N1 N 0.9302(6) 0.22955(16) 0.26924(9) 0.0410(6) Uani 1 1 d .
N2 N 0.0229(7) 0.24315(18) 0.16159(10) 0.0439(6) Uani 1 1 d .
N3 N 0.4175(7) 0.36760(18) -0.00182(10) 0.0494(7) Uani 1 1 d .
H3A H 0.4895 0.4157 -0.0212 0.059 Uiso 1 1 calc R
H3B H 0.4137 0.3071 -0.0136 0.059 Uiso 1 1 calc R
O1 O 0.7096(7) 0.39330(16) 0.22299(8) 0.0576(6) Uani 1 1 d .
O2 O 0.5560(7) 0.46807(15) 0.29505(9) 0.0579(7) Uani 1 1 d .
O3 O 0.4996(7) 0.43154(16) 0.38610(9) 0.0596(7) Uani 1 1 d .
O4 O 0.6222(8) 0.31223(17) 0.44341(8) 0.0656(7) Uani 1 1 d .
O5 O 0.3122(7) 0.47128(15) 0.06499(9) 0.0618(7) Uani 1 1 d .
O6 O 0.694(2) 0.5063(8) 0.5008(4) 0.245(4) Uani 1 1 d .
H2O H 0.522(15) 0.446(4) 0.329(2) 0.13(2) 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 123.0(2)
O1 C1 C2 118.3(2)
O2 C1 C2 118.7(2)
O1 C1 H2O 152.4(18)
O2 C1 H2O 30.1(18)
C2 C1 H2O 89.0(18)
N1 C2 C6 120.5(2)
N1 C2 C1 110.1(2)
C6 C2 C1 129.4(2)
N1 C3 C4 122.7(2)
N1 C3 H3 118.6
C4 C3 H3 118.6
C3 C4 C5 117.8(2)
C3 C4 H4 121.1
C5 C4 H4 121.1
C4 C5 C6 121.5(3)
C4 C5 H5 119.3
C6 C5 H5 119.3
C5 C6 C2 117.3(2)
C5 C6 C7 114.1(2)
C2 C6 C7 128.7(2)
O4 C7 O3 122.2(3)
O4 C7 C6 118.6(3)
O3 C7 C6 119.1(2)
O5 C8 N3 122.9(2)
O5 C8 C9 119.5(2)
N3 C8 C9 117.5(2)
C10 C9 C13 118.2(2)
C10 C9 C8 124.8(2)
C13 C9 C8 117.0(2)
C11 C10 C9 120.5(3)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C11 C12 119.1(3)
C10 C11 H11 120.5
C12 C11 H11 120.5
N2 C12 C11 120.4(2)
N2 C12 H12 119.8
C11 C12 H12 119.8
N2 C13 C9 120.5(2)
N2 C13 H13 119.7
C9 C13 H13 119.7
C3 N1 C2 120.2(2)
C12 N2 C13 121.4(3)
C12 N2 H2N 114(2)
C13 N2 H2N 125(2)
C8 N3 H3A 120.0
C8 N3 H3B 120.0
H3A N3 H3B 120.0
C1 O2 H2O 106(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.211(3) .
C1 O2 1.278(3) .
C1 C2 1.542(3) .
C1 H2O 1.78(5) .
C2 N1 1.355(3) .
C2 C6 1.405(4) .
C3 N1 1.339(4) .
C3 C4 1.370(4) .
C3 H3 0.9300 .
C4 C5 1.373(4) .
C4 H4 0.9300 .
C5 C6 1.400(4) .
C5 H5 0.9300 .
C6 C7 1.531(4) .
C7 O4 1.214(3) .
C7 O3 1.281(4) .
C8 O5 1.228(3) .
C8 N3 1.321(4) .
C8 C9 1.504(3) .
C9 C10 1.383(4) .
C9 C13 1.383(4) .
C10 C11 1.374(4) .
C10 H10 0.9300 .
C11 C12 1.374(4) .
C11 H11 0.9300 .
C12 N2 1.338(4) .
C12 H12 0.9300 .
C13 N2 1.344(3) .
C13 H13 0.9300 .
N2 H2N 1.01(4) .
N3 H3A 0.8600 .
N3 H3B 0.8600 .
O2 H2O 0.93(5) .
O6 O6 1.448(15) 3_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
O1 C1 C2 N1 1.8(4)
O2 C1 C2 N1 -177.2(3)
O1 C1 C2 C6 -177.6(3)
O2 C1 C2 C6 3.3(4)
N1 C3 C4 C5 0.0(4)
C3 C4 C5 C6 -0.1(4)
C4 C5 C6 C2 -0.2(4)
C4 C5 C6 C7 179.1(3)
N1 C2 C6 C5 0.5(4)
C1 C2 C6 C5 179.9(3)
N1 C2 C6 C7 -178.6(3)
C1 C2 C6 C7 0.8(5)
C5 C6 C7 O4 -1.1(4)
C2 C6 C7 O4 178.0(3)
C5 C6 C7 O3 -179.6(3)
C2 C6 C7 O3 -0.5(5)
O5 C8 C9 C10 167.4(3)
N3 C8 C9 C10 -12.4(4)
O5 C8 C9 C13 -11.1(4)
N3 C8 C9 C13 169.1(3)
C13 C9 C10 C11 0.3(4)
C8 C9 C10 C11 -178.2(3)
C9 C10 C11 C12 -0.6(5)
C10 C11 C12 N2 0.4(5)
C10 C9 C13 N2 0.2(4)
C8 C9 C13 N2 178.8(2)
C4 C3 N1 C2 0.3(4)
C6 C2 N1 C3 -0.5(4)
C1 C2 N1 C3 180.0(2)
C11 C12 N2 C13 0.1(4)
C9 C13 N2 C12 -0.4(4)
