#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/59/2015903.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_2015903
loop_
_publ_author_name
'Ludvík, Jir̆í '
'Urban, Jir̆í '
'Fábry, Jan'
'Císar̆ová, Ivana'
_publ_section_title
;
 4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (metamitron)
 and 4-amino-6-methyl-3-phenyl-1,2,4-triazin-5(4H)-one
 (isometamitron)
;
_journal_coeditor_code           GG3068
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o259
_journal_page_last               o262
_journal_paper_doi               10.1107/S0108270107009596
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H10 N4 O'
_chemical_formula_moiety         'C10 H10 N4 O'
_chemical_formula_sum            'C10 H10 N4 O'
_chemical_formula_weight         202.22
_chemical_melting_point          442
_chemical_name_common            metamitron
_chemical_name_systematic
;
4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_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            8
_cell_length_a                   9.5433(2)
_cell_length_b                   9.1416(2)
_cell_length_c                   21.8652(4)
_cell_measurement_reflns_used    20449
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1
_cell_volume                     1907.54(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'HKL Denzo (Otwinowski & Minor, 1997) and Scalepack'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            4037
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.61
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.173
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0388
_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)+(0.0473P)²+0.4343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                1816
_reflns_number_total             2172
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3068.cif
_cod_data_source_block           I
_cod_database_code               2015903
_cod_database_fobs_code          2015903
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x+1/2, y+1/2, z'
'x+1/2, y, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
'x-1/2, -y-1/2, -z'
'-x-1/2, -y, z-1/2'
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 0.52246(10) 0.33863(11) 0.55975(4) 0.0303(2) Uani d . 1
N N2 0.51372(11) 0.30930(11) 0.49829(5) 0.0327(3) Uani d . 1
N N4 0.73621(10) 0.41068(10) 0.48514(4) 0.0273(2) Uani d . 1
N N14 0.84248(11) 0.45224(13) 0.44339(5) 0.0349(3) Uani d . 1
O O15 0.85921(9) 0.50747(12) 0.56381(4) 0.0450(3) Uani d . 1
C C3 0.61899(12) 0.34511(12) 0.46302(5) 0.0284(3) Uani d . 1
C C5 0.75262(12) 0.44546(13) 0.54638(5) 0.0291(3) Uani d . 1
C C6 0.63274(11) 0.40094(12) 0.58377(5) 0.0262(3) Uani d . 1
C C7 0.63123(12) 0.42502(12) 0.65095(5) 0.0275(3) Uani d . 1
C C8 0.54034(14) 0.34282(14) 0.68712(6) 0.0352(3) Uani d . 1
C C9 0.53178(15) 0.36659(15) 0.74954(6) 0.0408(3) Uani d . 1
C C10 0.61393(15) 0.47204(15) 0.77706(6) 0.0402(3) Uani d . 1
C C11 0.70411(15) 0.55361(16) 0.74189(6) 0.0425(3) Uani d . 1
C C12 0.71363(13) 0.53109(14) 0.67920(6) 0.0369(3) Uani d . 1
C C13 0.61174(14) 0.31096(15) 0.39650(5) 0.0370(3) Uani d . 1
H H8 0.4848 0.2712 0.6691 0.042 Uiso calc R 1
H H9 0.4703 0.3112 0.7731 0.049 Uiso calc R 1
H H10 0.6083 0.4877 0.8190 0.048 Uiso calc R 1
H H11 0.7595 0.6248 0.7603 0.051 Uiso calc R 1
H H12 0.7753 0.5871 0.6560 0.044 Uiso calc R 1
H H13A 0.5229 0.2668 0.3873 0.056 Uiso calc R 1
H H13B 0.6857 0.2445 0.3859 0.056 Uiso calc R 1
H H13C 0.6219 0.3996 0.3734 0.056 Uiso calc R 1
H H141 0.9004(18) 0.5183(19) 0.4663(8) 0.058(5) Uiso d . 1
H H142 0.8956(17) 0.368(2) 0.4380(7) 0.059(5) Uiso d . 1
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
C6 N1 N2 121.83(9)
C3 N4 C5 122.59(9)
C3 N4 N14 118.60(9)
C5 N4 N14 118.72(10)
O15 C5 N4 120.05(10)
O15 C5 C6 127.13(11)
N4 C5 C6 112.82(10)
N1 C6 C5 121.74(10)
N1 C6 C7 117.01(10)
C5 C6 C7 121.25(10)
C3 N2 N1 118.78(10)
N4 N14 H141 104.1(10)
N4 N14 H142 104.6(10)
H141 N14 H142 105.8(14)
N2 C3 N4 122.22(10)
N2 C3 C13 119.18(11)
N4 C3 C13 118.59(10)
C3 C13 H13A 109.5
C3 C13 H13B 109.5
H13A C13 H13B 109.5
C3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C7 C8 118.37(11)
C12 C7 C6 122.42(11)
C8 C7 C6 119.16(10)
C9 C8 C7 120.76(12)
C9 C8 H8 119.6
C7 C8 H8 119.6
C10 C9 C8 120.38(12)
C10 C9 H9 119.8
C8 C9 H9 119.8
C11 C10 C9 119.38(12)
C11 C10 H10 120.3
C9 C10 H10 120.3
C10 C11 C12 120.86(12)
C10 C11 H11 119.6
C12 C11 H11 119.6
C11 C12 C7 120.25(12)
C11 C12 H12 119.9
C7 C12 H12 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.3069(14)
N1 N2 1.3729(13)
O15 C5 1.2254(14)
N4 C3 1.3582(15)
N4 C5 1.3850(14)
N4 N14 1.4163(13)
C5 C6 1.4638(16)
C6 C7 1.4854(15)
N2 C3 1.3081(15)
N14 H141 0.960(18)
N14 H142 0.928(19)
C3 C13 1.4893(16)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C7 C12 1.3929(17)
C7 C8 1.3937(17)
C8 C9 1.3844(18)
C8 H8 0.9300
C9 C10 1.3806(19)
C9 H9 0.9300
C10 C11 1.3741(19)
C10 H10 0.9300
C11 C12 1.3891(17)
C11 H11 0.9300
C12 H12 0.9300
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
N14 H141 O15 . 0.960(18) 2.169(17) 2.6856(14) 112.3(12)
N14 H141 O15 5_766 0.960(18) 2.398(17) 2.8749(13) 110.2(12)
N14 H142 N1 7_666 0.928(19) 2.245(19) 3.1663(15) 171.3(14)
N14 H142 N2 7_666 0.928(19) 2.418(18) 3.1643(15) 137.4(13)
C12 H12 O15 . 0.93 2.29 2.8883(16) 122
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
N1 C6 C7 C8 20.31(15)
C5 C6 C7 C8 -159.76(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 35563
