#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:19:21 +0100 (jue 24 de mar de 2016) $
#$Revision: 179624 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/88/4508864.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4508864
loop_
_publ_author_name
'Babu, N. Jagadeesh'
'Nangia, Ashwini'
_publ_section_title
;
 Water-Mediated Multicenter Synthon and Aromatic C−H → N
 Isostructurality
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1753
_journal_paper_doi               10.1021/cg060378u
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety         'C8 H5 N O6, 2(H2 O) '
_chemical_formula_sum            'C8 H9 N O8'
_chemical_formula_weight         247.16
_chemical_melting_point          508
_chemical_name_systematic
; 
 Pyridine-2,4,6-tricarboxylic acid 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9452(12)
_cell_length_b                   9.4204(19)
_cell_length_c                   18.370(4)
_cell_measurement_reflns_used    2954
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.90
_cell_measurement_theta_min      2.43
_cell_volume                     1028.8(4)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5714
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_correction_T_min  0.9211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0407
_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)+(0.0563P)²+0.1326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                1097
_reflns_number_total             1213
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060378usup3.cif
_cod_data_source_block           an339_m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               4508864
loop_
_symmetry_equiv_pos_as_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'
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
O4 O 1.0988(4) 0.1924(2) 0.96076(11) 0.0410(5) Uani 1 1 d .
C6 C 0.4095(5) -0.2264(2) 0.83736(15) 0.0323(6) Uani 1 1 d .
C1 C 0.5157(4) -0.0858(3) 0.85449(13) 0.0285(6) Uani 1 1 d .
N1 N 0.4031(4) 0.0280(2) 0.83021(12) 0.0290(5) Uani 1 1 d .
O3 O 1.0983(4) -0.0417(2) 0.97801(13) 0.0471(6) Uani 1 1 d .
O6 O 0.4243(4) 0.40138(18) 0.84682(14) 0.0581(7) Uani 1 1 d .
O2 O 0.2434(4) -0.2409(2) 0.80165(14) 0.0550(7) Uani 1 1 d .
O5 O 0.1824(4) 0.2661(2) 0.78725(12) 0.0427(6) Uani 1 1 d .
O7 O 0.0279(4) 0.0036(2) 0.72069(13) 0.0435(5) Uani 1 1 d .
C5 C 0.4886(4) 0.1556(2) 0.84689(14) 0.0273(5) Uani 1 1 d .
C4 C 0.6868(4) 0.1731(3) 0.88496(15) 0.0303(6) Uani 1 1 d .
H4 H 0.7420 0.2637 0.8942 0.036 Uiso 1 1 calc R
C2 C 0.7144(4) -0.0772(3) 0.89387(14) 0.0306(6) Uani 1 1 d .
H2 H 0.7869 -0.1591 0.9096 0.037 Uiso 1 1 calc R
C8 C 0.3598(5) 0.2862(2) 0.82629(15) 0.0313(6) Uani 1 1 d .
O1 O 0.5259(4) -0.3310(2) 0.86574(14) 0.0578(7) Uani 1 1 d .
C3 C 0.8027(5) 0.0550(3) 0.90924(15) 0.0297(6) Uani 1 1 d .
C7 C 1.0159(5) 0.0768(3) 0.95188(14) 0.0318(6) Uani 1 1 d .
O8 O 0.0434(5) 0.9946(3) 0.55786(18) 0.0542(7) Uani 1 1 d .
H7B H -0.027(6) 0.091(4) 0.7185(18) 0.058(10) Uiso 1 1 d .
H8B H 0.049(7) 1.008(4) 0.599(2) 0.060(13) Uiso 1 1 d .
H5 H 0.117(7) 0.348(4) 0.7819(18) 0.057(10) Uiso 1 1 d .
H1 H 0.477(7) -0.406(4) 0.854(2) 0.064(12) Uiso 1 1 d .
H7A H 0.133(7) 0.008(4) 0.751(2) 0.065(12) Uiso 1 1 d .
H3 H 1.215(7) -0.025(4) 1.004(2) 0.068(12) Uiso 1 1 d .
H8A H -0.007(9) 0.920(5) 0.553(3) 0.086(18) Uiso 1 1 d .
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
O4 0.0376(11) 0.0367(10) 0.0486(12) -0.0056(9) -0.0099(10) -0.0059(9)
C6 0.0405(15) 0.0213(12) 0.0351(15) -0.0002(11) -0.0045(13) -0.0039(11)
C1 0.0329(13) 0.0218(12) 0.0308(13) 0.0012(10) 0.0004(12) -0.0001(11)
N1 0.0350(11) 0.0198(9) 0.0323(12) -0.0007(9) -0.0029(10) 0.0001(9)
O3 0.0448(12) 0.0398(12) 0.0567(14) 0.0064(10) -0.0222(12) -0.0018(10)
O6 0.0567(14) 0.0167(9) 0.1009(19) -0.0044(11) -0.0312(14) -0.0002(9)
O2 0.0598(15) 0.0272(10) 0.0780(17) 0.0014(10) -0.0339(13) -0.0072(10)
O5 0.0485(12) 0.0242(10) 0.0553(14) -0.0039(9) -0.0203(11) 0.0062(9)
O7 0.0459(12) 0.0274(11) 0.0572(14) -0.0022(10) -0.0164(11) -0.0039(10)
C5 0.0294(13) 0.0201(11) 0.0324(13) -0.0003(10) 0.0000(13) -0.0014(10)
C4 0.0331(12) 0.0208(11) 0.0371(15) -0.0039(11) 0.0029(13) -0.0033(11)
C2 0.0359(14) 0.0201(11) 0.0356(15) 0.0034(11) -0.0032(12) 0.0010(11)
C8 0.0354(15) 0.0200(12) 0.0386(16) -0.0003(11) -0.0008(12) -0.0012(10)
O1 0.0628(14) 0.0170(10) 0.0936(19) 0.0042(10) -0.0336(15) -0.0044(10)
C3 0.0305(13) 0.0285(13) 0.0301(14) -0.0015(11) 0.0031(12) -0.0006(10)
C7 0.0328(14) 0.0324(14) 0.0301(13) -0.0011(11) -0.0013(13) -0.0001(12)
O8 0.0495(15) 0.0602(17) 0.0528(17) 0.0028(14) 0.0127(13) -0.0023(14)
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
O2 C6 O1 124.7(2)
O2 C6 C1 124.4(2)
O1 C6 C1 111.0(2)
N1 C1 C2 123.5(2)
N1 C1 C6 115.2(2)
C2 C1 C6 121.3(2)
C1 N1 C5 116.8(2)
C7 O3 H3 110(3)
C8 O5 H5 107(2)
H7B O7 H7A 105(3)
N1 C5 C4 123.2(2)
N1 C5 C8 119.0(2)
C4 C5 C8 117.8(2)
C5 C4 C3 119.5(2)
C5 C4 H4 120.2
C3 C4 H4 120.2
C3 C2 C1 118.9(2)
C3 C2 H2 120.6
C1 C2 H2 120.6
O6 C8 O5 124.3(2)
O6 C8 C5 119.7(3)
O5 C8 C5 116.0(2)
C6 O1 H1 112(3)
C2 C3 C4 118.1(2)
C2 C3 C7 123.4(2)
C4 C3 C7 118.6(2)
O4 C7 O3 124.5(3)
O4 C7 C3 122.6(2)
O3 C7 C3 112.9(2)
H8B O8 H8A 107(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C7 1.206(3)
C6 O2 1.193(3)
C6 O1 1.313(3)
C6 C1 1.500(3)
C1 N1 1.340(3)
C1 C2 1.387(4)
N1 C5 1.341(3)
O3 C7 1.310(3)
O3 H3 0.85(4)
O6 C8 1.211(3)
O5 C8 1.289(3)
O5 H5 0.87(4)
O7 H7B 0.88(4)
O7 H7A 0.84(4)
C5 C4 1.380(4)
C5 C8 1.498(3)
C4 C3 1.382(4)
C4 H4 0.9300
C2 C3 1.381(3)
C2 H2 0.9300
O1 H1 0.79(4)
C3 C7 1.504(4)
O8 H8B 0.77(4)
O8 H8A 0.77(5)
