#------------------------------------------------------------------------------
#$Date: 2019-11-23 20:36:16 +0100 (Sat 23 de Nov de 2019) $
#$Revision: 235130 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/67/4036719.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_4036719
loop_
_publ_author_name
'List, Manuela'
'Puchinger, Helmut'
'Gabriel, Herbert'
'Monkowius, Uwe'
'Schwarzinger, Clemens'
_publ_section_title
;
 N-Methylmelamines: Synthesis, Characterization, and Physical Properties.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4066
_journal_page_last               4075
_journal_paper_doi               10.1021/acs.joc.6b00355
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C5 H10 N6'
_chemical_formula_sum            'C5 H10 N6'
_chemical_formula_weight         154.19
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_Hall           '-R 3 2"c'
_space_group_name_H-M_alt        'R -3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   20.343(5)
_cell_length_b                   20.343(5)
_cell_length_c                   9.880(3)
_cell_measurement_temperature    233.(2)
_cell_volume                     3540.9(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      233.(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SMART X2S'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'sealed MicroFocus tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1132
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19278
_diffrn_reflns_theta_full        24.91
_diffrn_reflns_theta_max         24.91
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1476
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.350
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.149
_refine_ls_extinction_coef       0.0020(8)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     54
_refine_ls_number_reflns         688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0442
_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)+(0.0771P)²+2.1861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1330
_reflns_number_gt                541
_reflns_number_total             688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00355_si_004.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'R -3 c'
_cod_database_code               4036719
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'y+2/3, x+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'y+1/3, x+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-y+2/3, -x+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-y+1/3, -x+2/3, z+1/6'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C3 0.25467(14) 0.75909(14) 0.3002(3) 0.0715(9) Uani d . 1
H H1 0.2754 0.8046 0.3552 0.107 Uiso calc R 1
H H2 0.295 0.7593 0.2475 0.107 Uiso calc R 1
H H3 0.2318 0.7148 0.3584 0.107 Uiso calc R 1
N N3 0.19795(9) 0.75695(9) 0.2105(2) 0.0522(6) Uani d . 1
H H5 0.1569 0.7135 0.1977 0.063 Uiso calc R 1
C C1 0.20423(10) 0.81732(9) 0.14553(18) 0.0342(5) Uani d . 1
N N1 0.14151(10) 0.80817(10) 0.0833 0.0369(6) Uani d S 1
N N2 0.27221(8) 0.88108(8) 0.14655(15) 0.0347(5) Uani d . 1
C C2 0.27358(11) 0.94024(11) 0.0833 0.0317(6) Uani d S 1
N N4 0.33905(10) 1.00572(10) 0.0833 0.0412(7) Uani d S 1
H H4A 0.3422 1.0453 0.0435 0.049 Uiso calc PR 0.5
H H4B 0.3787 1.0089 0.1232 0.049 Uiso calc PR 0.5
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C3 0.0547(15) 0.0546(14) 0.097(2) 0.0212(12) -0.0136(13) 0.0308(13)
N3 0.0361(9) 0.0286(9) 0.0825(14) 0.0090(7) -0.0108(9) 0.0147(8)
C1 0.0270(10) 0.0270(10) 0.0455(11) 0.0112(8) 0.0012(8) 0.0022(8)
N1 0.0259(8) 0.0259(8) 0.0548(14) 0.0098(9) -0.0031(5) 0.0031(5)
N2 0.0275(9) 0.0282(8) 0.0442(10) 0.0106(7) -0.0031(6) 0.0039(6)
C2 0.0277(10) 0.0277(10) 0.0333(13) 0.0091(11) 0.0003(5) -0.0003(5)
N4 0.0299(8) 0.0299(8) 0.0482(14) 0.0034(9) -0.0077(5) 0.0077(5)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N3 C3 H1 . . 109.5
N3 C3 H2 . . 109.5
H1 C3 H2 . . 109.5
N3 C3 H3 . . 109.5
H1 C3 H3 . . 109.5
H2 C3 H3 . . 109.5
C1 N3 C3 . . 124.23(17)
C1 N3 H5 . . 117.9
C3 N3 H5 . . 117.9
N3 C1 N2 . . 117.67(15)
N3 C1 N1 . . 116.46(16)
N2 C1 N1 . . 125.86(16)
C1 N1 C1 18_454 . 114.0(2)
C1 N2 C2 . . 114.34(15)
N4 C2 N2 . 18_454 117.27(11)
N4 C2 N2 . . 117.27(11)
N2 C2 N2 18_454 . 125.5(2)
C2 N4 H4A . . 120.0
C2 N4 H4B . . 120.0
H4A N4 H4B . . 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C3 N3 . 1.438(3)
C3 H1 . 0.97
C3 H2 . 0.97
C3 H3 . 0.97
N3 C1 . 1.334(2)
N3 H5 . 0.87
C1 N2 . 1.342(2)
C1 N1 . 1.343(2)
N1 C1 18_454 1.343(2)
N2 C2 . 1.3439(17)
C2 N4 . 1.332(3)
C2 N2 18_454 1.3438(17)
N4 H4A . 0.87
N4 H4B . 0.87
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_site_symmetry_4
_geom_torsion
C3 N3 C1 N2 . 11.2(3)
C3 N3 C1 N1 . -169.57(19)
N3 C1 N1 C1 18_454 179.1(2)
N2 C1 N1 C1 18_454 -1.69(13)
N3 C1 N2 C2 . -177.73(15)
N1 C1 N2 C2 . 3.1(2)
C1 N2 C2 N4 . 178.58(11)
C1 N2 C2 N2 18_454 -1.42(11)
