#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:33:27 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179585 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/50/4505031.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_4505031
loop_
_publ_author_name
'Zhang, Xiu-Lian'
'Chen, Xiao-Ming'
_publ_section_title
;
 Supramolecular Architectures and Helical Water Chains in Cocrystals of
 Melamine and Aromatic Carboxylic Acids
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              617
_journal_paper_doi               10.1021/cg0498251
_journal_volume                  5
_journal_year                    2005
_chemical_formula_sum            'C13 H16 N6 O7'
_chemical_formula_weight         368.32
_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                 93.80(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.139(3)
_cell_length_b                   8.164(2)
_cell_length_c                   14.947(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1599.8(6)
_computing_cell_refinement       'SHELXTL-Plus (Sheldrick, 1990)'
_computing_data_collection       'SHELXTL-Plus (Sheldrick, 1990)'
_computing_data_reduction        'SHELXTL-Plus (Sheldrick, 1990)'
_computing_molecular_graphics    'SHELXTL V. 6.10 (Sheldrick, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8205
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.126
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.001(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1149P)²+0.8170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1614
_reflns_number_gt                2769
_reflns_number_total             3051
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0498251si20040530_094328.cif
_cod_data_source_block           complex_4
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               4505031
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
O1 O 0.42440(10) 0.4523(2) 0.28644(11) 0.0516(5) Uani 1 1 d .
H1C H 0.3717 0.5007 0.2634 0.080 Uiso 1 1 d R
O2 O 0.34388(10) 0.4565(2) 0.42287(12) 0.0514(4) Uani 1 1 d .
O3 O 0.67573(11) -0.0203(2) 0.67493(11) 0.0507(4) Uani 1 1 d .
O4 O 0.74258(10) -0.05618(19) 0.52940(11) 0.0500(4) Uani 1 1 d .
O5 O 0.78377(9) 0.25699(17) 0.41781(9) 0.0365(4) Uani 1 1 d .
O6 O 0.71615(9) 0.09554(19) 0.30204(10) 0.0418(4) Uani 1 1 d .
N1 N 1.01236(13) 0.3329(2) 0.41861(12) 0.0459(5) Uani 1 1 d .
H1A H 1.0716 0.3685 0.4455 0.080 Uiso 1 1 d R
H1B H 0.9625 0.2960 0.4519 0.080 Uiso 1 1 d R
N2 N 0.91454(10) 0.2871(2) 0.27891(11) 0.0333(4) Uani 1 1 d .
H2A H 0.8634 0.2550 0.3121 0.080 Uiso 1 1 d R
N3 N 0.82038(11) 0.2216(2) 0.13975(12) 0.0388(4) Uani 1 1 d .
H3A H 0.7717 0.1817 0.1733 0.080 Uiso 1 1 d R
H3B H 0.8118 0.2184 0.0795 0.080 Uiso 1 1 d R
N4 N 0.95805(11) 0.3326(2) 0.11285(11) 0.0348(4) Uani 1 1 d .
N5 N 1.09802(12) 0.4406(2) 0.09973(13) 0.0435(4) Uani 1 1 d .
H5B H 1.1589 0.4837 0.1181 0.080 Uiso 1 1 d R
H5C H 1.0788 0.4362 0.0408 0.080 Uiso 1 1 d R
N6 N 1.05971(11) 0.3844(2) 0.25964(12) 0.0383(4) Uani 1 1 d .
C1 C 0.41028(13) 0.4163(2) 0.38180(14) 0.0377(5) Uani 1 1 d .
C2 C 0.68569(13) 0.0073(2) 0.57667(14) 0.0357(4) Uani 1 1 d .
C3 C 0.71699(12) 0.1787(2) 0.38236(12) 0.0288(4) Uani 1 1 d .
C4 C 0.48386(12) 0.3177(2) 0.43374(13) 0.0333(4) Uani 1 1 d .
C5 C 0.47255(14) 0.2526(2) 0.52995(14) 0.0374(5) Uani 1 1 d .
H5A H 0.4125 0.2857 0.5585 0.080 Uiso 1 1 d R
C6 C 0.53854(13) 0.1554(2) 0.57745(13) 0.0349(4) Uani 1 1 d .
H6A H 0.5294 0.1151 0.6367 0.080 Uiso 1 1 d R
C7 C 0.61753(12) 0.1237(2) 0.53058(12) 0.0309(4) Uani 1 1 d .
C8 C 0.63086(12) 0.1942(2) 0.43547(12) 0.0288(4) Uani 1 1 d .
C9 C 0.56354(13) 0.2888(2) 0.38769(13) 0.0318(4) Uani 1 1 d .
H9A H 0.5722 0.3289 0.3283 0.080 Uiso 1 1 d R
C10 C 0.7417(2) -0.1272(4) 0.72718(19) 0.0658(8) Uani 1 1 d .
H10A H 0.7229 -0.1277 0.7882 0.080 Uiso 1 1 d R
H10B H 0.7353 -0.2359 0.7029 0.080 Uiso 1 1 d R
H10C H 0.8110 -0.0908 0.7253 0.080 Uiso 1 1 d R
C11 C 0.99674(13) 0.3359(2) 0.31859(13) 0.0336(4) Uani 1 1 d .
C12 C 0.89798(13) 0.2801(2) 0.17540(13) 0.0311(4) Uani 1 1 d .
C13 C 1.03692(13) 0.3844(2) 0.15889(13) 0.0333(4) Uani 1 1 d .
O1W O 1.18130(12) 0.3924(2) 0.52445(13) 0.0606(5) Uani 1 1 d .
H1WA H 1.2368 0.4166 0.5014 0.080 Uiso 1 1 d R
H1WB H 1.1793 0.3870 0.5811 0.080 Uiso 1 1 d R
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
C10 O3 C2 122.62(19)
C11 N2 C12 122.71(15)
C13 N4 C12 103.03(16)
C11 N6 C13 125.21(15)
O2 C1 C4 112.18(19)
O2 C1 O1 127.38(18)
C4 C1 O1 120.43(15)
O4 C2 C7 113.51(18)
O4 C2 O3 128.25(18)
C7 C2 O3 118.23(16)
O5 C3 O6 128.27(15)
O5 C3 C8 107.13(15)
O6 C3 C8 124.46(14)
C9 C4 C1 110.31(17)
C9 C4 C5 123.67(17)
C1 C4 C5 126.02(16)
C6 C5 C4 126.51(16)
C7 C6 C5 109.81(18)
C6 C7 C2 111.12(17)
C6 C7 C8 123.71(16)
C2 C7 C8 125.05(15)
C9 C8 C3 105.84(15)
C9 C8 C7 126.08(15)
C3 C8 C7 128.04(15)
C4 C9 C8 110.15(17)
N2 C11 N6 109.78(17)
N2 C11 N1 121.41(16)
N6 C11 N1 128.81(16)
N3 C12 N4 109.68(18)
N3 C12 N2 120.69(16)
N4 C12 N2 129.63(15)
N4 C13 N5 105.23(17)
N4 C13 N6 129.41(16)
N5 C13 N6 125.36(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.479(3)
O2 C1 1.147(2)
O3 C10 1.426(3)
O3 C2 1.500(3)
O4 C2 1.182(3)
O5 C3 1.182(2)
O6 C3 1.379(2)
N1 C11 1.496(3)
N2 C11 1.262(2)
N2 C12 1.549(2)
N3 C12 1.216(2)
N4 C13 1.278(2)
N4 C12 1.334(2)
N5 C13 1.316(2)
N6 C11 1.309(2)
N6 C13 1.516(3)
C1 C4 1.444(3)
C2 C7 1.448(3)
C3 C8 1.430(2)
C4 C9 1.312(2)
C4 C5 1.549(3)
C5 C6 1.343(3)
C6 C7 1.316(3)
C7 C8 1.554(3)
C8 C9 1.344(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1W 0.90 1.81 2.683(2) 162.3 .
N1 H1B O5 0.90 2.39 3.066(2) 131.8 .
N1 H1B N4 0.90 2.63 3.322(2) 134.5 4_566
N2 H2A O5 0.90 1.95 2.792(2) 154.6 .
N2 H2A O6 0.90 2.33 3.079(2) 140.7 .
N3 H3A O6 0.90 2.22 3.043(2) 152.3 .
N5 H5B O6 0.90 2.17 3.040(2) 163.5 2_755
N5 H5B O5 0.90 2.43 3.034(2) 125.1 2_755
O1W H1WA O2 0.85 1.92 2.752(2) 166.1 1_655
