#------------------------------------------------------------------------------
#$Date: 2016-02-16 21:30:59 +0100 (mar 16 de feb de 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/15/4001502.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_4001502
loop_
_publ_author_name
'Lotsch, Bettina V.'
'Schnick, Wolfgang'
_publ_section_title
;
 From Triazines to Heptazines:  Novel Nonmetal Tricyanomelaminates
 as Precursors for Graphitic Carbon Nitride Materials
;
_journal_issue                   7
_journal_name_full               'Chemistry of Materials'
_journal_page_first              1891
_journal_paper_doi               10.1021/cm052342f
_journal_volume                  18
_journal_year                    2006
_chemical_formula_moiety         'C6 H N9, 2(C3 H7 N6), 2(H2 O), 0.399(H2 O)'
_chemical_formula_sum            'C12 H19.8 N21 O2.4'
_chemical_formula_weight         496.69
_chemical_name_common            'Melaminium tricyanomelaminate hydrate'
_chemical_name_systematic
;                           Dimelaminium hydrogen tricyanomelaminate
                            hydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.22(3)
_cell_angle_beta                 112.74(3)
_cell_angle_gamma                104.62(3)
_cell_formula_units_Z            2
_cell_length_a                   10.295(2)
_cell_length_b                   11.203(2)
_cell_length_c                   11.207(2)
_cell_measurement_reflns_used    6098
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      3.134
_cell_volume                     1064.8(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       phi/omega-scan
_diffrn_radiation_monochromator  'vertically mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0589
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12076
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.44
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4111
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0570
_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)+(0.0496P)²+0.9337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                2671
_reflns_number_total             4111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm052342fsi20051025_084317.cif
_cod_data_source_block           p:\rechnung\test\MelaTCM
_cod_original_cell_volume        1064.8(4)
_cod_original_formula_sum        'C12 H19.80 N21 O2.40'
_cod_database_code               4001502
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N1 N 1.0402(2) 0.8710(2) 0.9179(2) 0.0248(5) Uani 1 1 d .
H1 H 1.1039 0.9543 0.9500 0.030 Uiso 1 1 calc R
N2 N 0.8452(2) 0.6786(2) 0.7275(2) 0.0242(5) Uani 1 1 d .
N3 N 0.9405(2) 0.6864(2) 0.9650(2) 0.0239(5) Uani 1 1 d .
N4 N 0.9628(2) 0.8755(2) 0.7019(2) 0.0281(5) Uani 1 1 d .
N5 N 0.8099(3) 0.7972(3) 0.4446(3) 0.0468(7) Uani 1 1 d .
N6 N 0.7472(2) 0.4994(2) 0.7833(2) 0.0275(5) Uani 1 1 d .
N7 N 0.5530(3) 0.3537(3) 0.5399(3) 0.0561(8) Uani 1 1 d .
N8 N 1.1408(2) 0.8864(2) 1.1438(2) 0.0290(5) Uani 1 1 d .
N9 N 1.1605(4) 0.8043(3) 1.3319(3) 0.0629(9) Uani 1 1 d .
N10 N 0.4823(2) 0.3360(2) 0.2240(2) 0.0262(5) Uani 1 1 d .
H10 H 0.5466 0.3768 0.3144 0.031 Uiso 1 1 calc R
N11 N 0.3920(2) 0.3404(2) -0.0011(2) 0.0256(5) Uani 1 1 d .
N12 N 0.2814(2) 0.1446(2) 0.0352(2) 0.0238(5) Uani 1 1 d .
N13 N 0.5845(2) 0.5248(2) 0.1909(2) 0.0309(5) Uani 1 1 d .
H13A H 0.5886 0.5688 0.1365 0.037 Uiso 1 1 calc R
H13B H 0.6463 0.5638 0.2818 0.037 Uiso 1 1 calc R
N14 N 0.1993(2) 0.1505(2) -0.1825(2) 0.0320(5) Uani 1 1 d .
H14A H 0.1333 0.0679 -0.2161 0.038 Uiso 1 1 calc R
H14B H 0.2030 0.1915 -0.2395 0.038 Uiso 1 1 calc R
N15 N 0.3794(2) 0.1497(2) 0.2601(2) 0.0306(5) Uani 1 1 d .
H15A H 0.3145 0.0672 0.2296 0.037 Uiso 1 1 calc R
H15B H 0.4449 0.1933 0.3499 0.037 Uiso 1 1 calc R
N16 N 0.7066(2) 0.3476(2) 0.9412(2) 0.0317(5) Uani 1 1 d .
H16 H 0.7157 0.3950 0.8906 0.038 Uiso 1 1 calc R
N17 N 0.5825(3) 0.1468(2) 0.9520(3) 0.0339(6) Uani 1 1 d .
N18 N 0.7926(3) 0.3303(2) 1.1604(3) 0.0335(6) Uani 1 1 d .
N19 N 0.5070(3) 0.1736(3) 0.7425(3) 0.0452(7) Uani 1 1 d .
H19A H 0.4360 0.0921 0.6994 0.054 Uiso 1 1 calc R
H19B H 0.5176 0.2234 0.6945 0.054 Uiso 1 1 calc R
N20 N 0.6722(3) 0.1345(3) 1.1688(3) 0.0409(6) Uani 1 1 d .
H20A H 0.7348 0.1693 1.2596 0.049 Uiso 1 1 calc R
H20B H 0.6026 0.0526 1.1293 0.049 Uiso 1 1 calc R
N21 N 0.9018(3) 0.5239(2) 1.1383(3) 0.0365(6) Uani 1 1 d .
H21A H 0.9644 0.5614 1.2292 0.044 Uiso 1 1 calc R
H21B H 0.9063 0.5691 1.0850 0.044 Uiso 1 1 calc R
C1 C 0.9451(3) 0.8041(2) 0.7777(3) 0.0232(6) Uani 1 1 d .
C2 C 0.8465(3) 0.6250(2) 0.8243(3) 0.0224(5) Uani 1 1 d .
C3 C 1.0381(3) 0.8108(2) 1.0093(3) 0.0229(6) Uani 1 1 d .
C4 C 0.8748(3) 0.8255(3) 0.5640(3) 0.0307(6) Uani 1 1 d .
C5 C 0.6480(3) 0.4290(3) 0.6498(3) 0.0331(7) Uani 1 1 d .
C6 C 1.1446(3) 0.8363(3) 1.2389(3) 0.0360(7) Uani 1 1 d .
C7 C 0.4859(3) 0.4005(2) 0.1362(3) 0.0238(6) Uani 1 1 d .
C8 C 0.2930(3) 0.2131(2) -0.0465(3) 0.0236(6) Uani 1 1 d .
C9 C 0.3787(3) 0.2075(2) 0.1717(3) 0.0240(6) Uani 1 1 d .
C10 C 0.5977(3) 0.2211(3) 0.8792(3) 0.0324(6) Uani 1 1 d .
C11 C 0.6827(3) 0.2055(3) 1.0915(3) 0.0323(7) Uani 1 1 d .
C12 C 0.8012(3) 0.4000(3) 1.0821(3) 0.0296(6) Uani 1 1 d .
O1 O 0.2147(3) 0.4863(2) 0.5447(2) 0.0477(6) Uani 1 1 d D
H1A H 0.206(4) 0.441(3) 0.461(3) 0.071 Uiso 1 1 d D
H1B H 0.172(4) 0.544(3) 0.523(4) 0.071 Uiso 1 1 d D
O2 O 0.0859(4) 0.6664(4) 0.4933(5) 0.1094(15) Uani 1 1 d D
H2A H 0.094(6) 0.713(5) 0.443(6) 0.164 Uiso 1 1 d D
H2B H -0.012(4) 0.614(6) 0.452(6) 0.164 Uiso 1 1 d D
O3 O 0.2378(7) -0.0585(6) 0.5935(6) 0.053(2) Uani 0.399(7) 1 d PD
H3A H 0.323(7) -0.081(10) 0.618(8) 0.080 Uiso 0.399(7) 1 d PD
H3B H 0.202(9) -0.091(9) 0.498(3) 0.080 Uiso 0.399(7) 1 d PD
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
C1 N1 C3 120.9(2)
C1 N1 H1 119.5
C3 N1 H1 119.5
C1 N2 C2 115.9(2)
C3 N3 C2 115.5(2)
C4 N4 C1 120.9(2)
C5 N6 C2 120.2(2)
C6 N8 C3 118.6(2)
C7 N10 C9 120.1(2)
C7 N10 H10 120.0
C9 N10 H10 120.0
C7 N11 C8 115.9(2)
C9 N12 C8 116.5(2)
C7 N13 H13A 120.0
C7 N13 H13B 120.0
H13A N13 H13B 120.0
C8 N14 H14A 120.0
C8 N14 H14B 120.0
H14A N14 H14B 120.0
C9 N15 H15A 120.0
C9 N15 H15B 120.0
H15A N15 H15B 120.0
C12 N16 C10 119.3(2)
C12 N16 H16 120.3
C10 N16 H16 120.3
C10 N17 C11 115.2(2)
C12 N18 C11 115.6(3)
C10 N19 H19A 120.0
C10 N19 H19B 120.0
H19A N19 H19B 120.0
C11 N20 H20A 120.0
C11 N20 H20B 120.0
H20A N20 H20B 120.0
C12 N21 H21A 120.0
C12 N21 H21B 120.0
H21A N21 H21B 120.0
N4 C1 N2 125.9(2)
N4 C1 N1 113.8(2)
N2 C1 N1 120.3(2)
N6 C2 N3 113.8(2)
N6 C2 N2 120.0(2)
N3 C2 N2 126.2(2)
N3 C3 N8 124.0(2)
N3 C3 N1 121.1(2)
N8 C3 N1 114.8(2)
N5 C4 N4 171.1(3)
N7 C5 N6 170.0(3)
N9 C6 N8 173.0(3)
N13 C7 N11 120.6(2)
N13 C7 N10 118.2(2)
N11 C7 N10 121.2(2)
N14 C8 N12 117.0(2)
N14 C8 N11 117.2(2)
N12 C8 N11 125.8(2)
N15 C9 N12 121.6(2)
N15 C9 N10 117.9(2)
N12 C9 N10 120.5(2)
N19 C10 N17 120.4(3)
N19 C10 N16 117.8(2)
N17 C10 N16 121.8(3)
N20 C11 N18 116.3(3)
N20 C11 N17 117.4(3)
N18 C11 N17 126.3(2)
N21 C12 N18 120.9(3)
N21 C12 N16 117.3(2)
N18 C12 N16 121.7(3)
H1A O1 H1B 101(3)
H2A O2 H2B 106(4)
H3A O3 H3B 97(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.361(3)
N1 C3 1.361(3)
N1 H1 0.8800
N2 C1 1.337(3)
N2 C2 1.360(3)
N3 C3 1.329(3)
N3 C2 1.359(3)
N4 C4 1.326(3)
N4 C1 1.332(3)
N5 C4 1.154(3)
N6 C5 1.318(4)
N6 C2 1.353(3)
N7 C5 1.152(4)
N8 C6 1.314(3)
N8 C3 1.340(3)
N9 C6 1.149(4)
N10 C7 1.363(3)
N10 C9 1.371(3)
N10 H10 0.8800
N11 C7 1.329(3)
N11 C8 1.357(3)
N12 C9 1.331(3)
N12 C8 1.350(3)
N13 C7 1.315(3)
N13 H13A 0.8800
N13 H13B 0.8800
N14 C8 1.320(3)
N14 H14A 0.8800
N14 H14B 0.8800
N15 C9 1.308(3)
N15 H15A 0.8800
N15 H15B 0.8800
N16 C12 1.362(4)
N16 C10 1.365(4)
N16 H16 0.8800
N17 C10 1.323(3)
N17 C11 1.358(4)
N18 C12 1.322(3)
N18 C11 1.352(4)
N19 C10 1.321(4)
N19 H19A 0.8800
N19 H19B 0.8800
N20 C11 1.328(3)
N20 H20A 0.8800
N20 H20B 0.8800
N21 C12 1.318(3)
N21 H21A 0.8800
N21 H21B 0.8800
O1 H1A 0.91(2)
O1 H1B 0.90(3)
O2 H2A 0.87(3)
O2 H2B 0.88(3)
O3 H3A 0.93(3)
O3 H3B 0.92(3)
