#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/94/2219441.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2219441
loop_
_publ_author_name
'Portalone, Gustavo'
_publ_section_title
;
 Acetoguanamine N,N-dimethylformamide solvate
;
_journal_coeditor_code           TK2285
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1685
_journal_paper_doi               10.1107/S1600536808023842
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C4 H7 N5, C3 H7 N O'
_chemical_formula_moiety         'C4 H7 N5, C3 H7 N O'
_chemical_formula_sum            'C7 H14 N6 O'
_chemical_formula_weight         198.24
_chemical_name_common
;
Acetoguanamine N,N-dimethylformamide solvate
;
_chemical_name_systematic
;2,4-diamino-6-methyl-1,3,5-triazine N,N-dimethylformamide
 solvate
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   25.548(2)
_cell_length_b                   23.0626(19)
_cell_length_c                   7.2689(9)
_cell_measurement_reflns_used    11018
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.6
_cell_measurement_theta_min      3.0
_cell_volume                     4282.9(7)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics    'WinGX (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur S CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.064
_diffrn_reflns_av_sigmaI/netI    0.035
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            27177
_diffrn_reflns_theta_full        25.9
_diffrn_reflns_theta_max         25.9
_diffrn_reflns_theta_min         3.0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablets
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.91
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1127
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.91
_refine_ls_R_factor_all          0.074
_refine_ls_R_factor_gt           0.047
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0841P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.119
_refine_ls_wR_factor_ref         0.127
_reflns_number_gt                698
_reflns_number_total             1127
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2285.cif
_cod_data_source_block           I
_cod_original_cell_volume        4282.8(7)
_cod_database_code               2219441
_cod_database_fobs_code          2219441
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
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
N N1 0.63312(11) 0.10945(11) 0.5765(4) 0.0495(9) Uani d . 1
C C2 0.58170(12) 0.10315(14) 0.6030(6) 0.0431(9) Uani d . 1
N N3 0.55453(10) 0.05414(12) 0.5797(4) 0.0447(8) Uani d . 1
C C4 0.58328(13) 0.00862(13) 0.5267(5) 0.0416(9) Uani d . 1
N N5 0.63552(11) 0.01049(12) 0.4927(5) 0.0471(8) Uani d . 1
C C6 0.65836(13) 0.06118(15) 0.5210(5) 0.0463(9) Uani d . 1
N N6 0.55533(11) 0.15017(12) 0.6581(5) 0.0592(10) Uani d . 1
H H6A 0.5721 0.1836 0.6753 0.071 Uiso calc R 1
H H6B 0.5210 0.14808 0.6776 0.071 Uiso calc R 1
N N7 0.55992(11) -0.04163(11) 0.5010(5) 0.0598(10) Uani d . 1
H H7A 0.5282 -0.04463 0.5175 0.072 Uiso calc R 1
H H7B 0.5771 -0.0700 0.4684 0.072 Uiso calc R 1
C C8 0.71557(14) 0.06575(18) 0.4923(7) 0.0710(13) Uani d . 1
H H8A 0.7319 0.0329 0.5395 0.106 Uiso calc R 1
H H8B 0.7282 0.0985 0.5522 0.106 Uiso calc R 1
H H8C 0.7226 0.0687 0.3671 0.106 Uiso calc R 1
O O1 0.44754(15) 0.1783(2) 0.7397(7) 0.1196(16) Uani d . 1
N N8 0.36343(14) 0.20435(17) 0.7802(5) 0.0738(11) Uani d . 1
C C9 0.4016(3) 0.1667(3) 0.7697(9) 0.113(2) Uani d . 1
H H9 0.3931 0.1279 0.7864 0.226 Uiso calc R 1
C C10 0.3107(3) 0.1868(4) 0.8156(11) 0.160(4) Uani d . 1
H H10A 0.2905 0.1891 0.7028 0.319 Uiso calc R 1
H H10B 0.2954 0.2122 0.9074 0.319 Uiso calc R 1
H H10C 0.3105 0.1472 0.8606 0.319 Uiso calc R 1
C C11 0.3722(4) 0.2647(2) 0.7568(11) 0.140(3) Uani d . 1
H H11A 0.3839 0.2813 0.8722 0.279 Uiso calc R 1
H H11B 0.3399 0.2833 0.7189 0.279 Uiso calc R 1
H H11C 0.3988 0.2706 0.6634 0.279 Uiso calc R 1
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
N1 0.0426(16) 0.0337(16) 0.072(2) -0.0041(13) -0.0033(15) -0.0092(16)
C2 0.0385(18) 0.0307(18) 0.060(2) -0.0004(15) -0.0048(19) -0.0032(16)
N3 0.0391(14) 0.0311(14) 0.0638(19) -0.0001(13) -0.0004(15) -0.0059(14)
C4 0.0400(19) 0.0273(17) 0.057(2) -0.0005(14) 0.0046(18) -0.0045(15)
N5 0.0406(16) 0.0310(15) 0.070(2) -0.0008(12) -0.0009(16) -0.0103(15)
C6 0.0399(17) 0.0381(19) 0.061(2) -0.0037(16) -0.0027(18) -0.0038(18)
N6 0.0457(17) 0.0298(15) 0.102(3) 0.0009(13) -0.0020(18) -0.0156(17)
N7 0.0414(16) 0.0319(15) 0.106(3) -0.0013(13) 0.0115(19) -0.0126(18)
C8 0.042(2) 0.062(2) 0.108(4) -0.0064(19) 0.006(3) -0.019(3)
O1 0.063(2) 0.153(4) 0.143(4) 0.013(2) -0.005(3) -0.037(3)
N8 0.070(2) 0.072(3) 0.079(3) 0.006(2) 0.0083(19) -0.012(2)
C9 0.133(6) 0.109(5) 0.096(5) 0.018(5) -0.008(4) -0.017(4)
C10 0.101(5) 0.266(10) 0.112(5) -0.053(6) 0.036(4) -0.050(6)
C11 0.242(9) 0.073(4) 0.104(5) -0.002(4) 0.001(5) 0.008(4)
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'
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'
H H 0.0000 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
C2 N1 C6 115.1(3)
N1 C2 N3 125.8(3)
N1 C2 N6 116.8(3)
N3 C2 N6 117.5(3)
C2 N3 C4 114.5(3)
N7 C4 N3 118.9(3)
N7 C4 N5 116.6(3)
N3 C4 N5 124.5(3)
C6 N5 C4 115.7(3)
N5 C6 N1 124.4(3)
N5 C6 C8 118.5(3)
N1 C6 C8 117.1(3)
C2 N6 H6A 120.0
C2 N6 H6B 120.0
H6A N6 H6B 120.0
C4 N7 H7A 120.0
C4 N7 H7B 120.0
H7A N7 H7B 120.0
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C9 N8 C11 121.7(6)
C9 N8 C10 121.7(6)
C11 N8 C10 116.6(6)
O1 C9 N8 125.6(7)
O1 C9 H9 117.2
N8 C9 H9 117.2
N8 C10 H10A 109.5
N8 C10 H10B 109.5
H10A C10 H10B 109.5
N8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N8 C11 H11A 109.5
N8 C11 H11B 109.5
H11A C11 H11B 109.5
N8 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.336(4)
N1 C6 1.348(5)
C2 N3 1.337(4)
C2 N6 1.338(4)
N3 C4 1.338(4)
C4 N7 1.317(4)
C4 N5 1.358(4)
N5 C6 1.323(4)
C6 C8 1.480(5)
N6 H6A 0.8907
N6 H6B 0.8907
N7 H7A 0.8226
N7 H7B 0.8226
C8 H8A 0.9300
C8 H8B 0.9300
C8 H8C 0.9300
O1 C9 1.223(7)
N8 C9 1.307(7)
N8 C11 1.419(6)
N8 C10 1.429(7)
C9 H9 0.9300
C10 H10A 0.9700
C10 H10B 0.9700
C10 H10C 0.9700
C11 H11A 0.9700
C11 H11B 0.9700
C11 H11C 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N6 H6B O1 . 0.89 2.05 2.890(5) 157
N6 H6A N5 3_655 0.89 2.13 3.022(4) 174
N7 H7B N1 7_644 0.82 2.18 2.989(4) 168
N7 H7A N3 2_655 0.82 2.17 2.993(4) 176
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
C6 N1 C2 N3 0.2(6)
C6 N1 C2 N6 180.0(4)
N1 C2 N3 C4 0.6(6)
N6 C2 N3 C4 -179.2(3)
C2 N3 C4 N7 179.7(4)
C2 N3 C4 N5 -1.8(5)
N7 C4 N5 C6 -179.4(4)
N3 C4 N5 C6 2.1(5)
C4 N5 C6 N1 -1.2(6)
C4 N5 C6 C8 178.1(4)
C2 N1 C6 N5 0.2(6)
C2 N1 C6 C8 -179.2(4)
C11 N8 C9 O1 0.0(10)
C10 N8 C9 O1 179.9(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655606
