#------------------------------------------------------------------------------
#$Date: 2011-09-20 12:45:16 +0300 (Tue, 20 Sep 2011) $
#$Revision: 1737 $
#$URL: svn://www.crystallography.net/cod-tools/tests/inputs/2203315.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_2203315
_space_group_IT_number           11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/m'
loop_
_publ_author_name
'Crockett, Rowena'
'Forrester, Alexander R.'
'Howie, R. Alan'
_publ_section_title
;
1,4-Diacetyl-1,2,4-triazolin-5-one
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o460
_journal_page_last               o461
_journal_volume                  60
_journal_year                    2004
_chemical_formula_moiety         'C6 H7 N3 O3'
_chemical_formula_sum            'C6 H7 N3 O3'
_chemical_formula_weight         169.15
_chemical_name_systematic
;
 1,4-Diacetyl-1,2,4-triazolin-5-one
;
_symmetry_cell_setting           monoclinic
_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                 104.54(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.572(3)
_cell_length_b                   6.199(3)
_cell_length_c                   9.463(3)
_cell_measurement_reflns_used    14
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.0
_cell_measurement_theta_min      11.0
_cell_volume                     373.2(3)
_computing_cell_refinement       'Nicolet P3 software'
_computing_data_collection       'Nicolet P3 software (Nicolet, 1980)'
_computing_data_reduction        'RDNIC (Howie, 1980)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nicolet P3 four-circle'
_diffrn_measurement_method       \q-2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1010
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.159
_refine_ls_extinction_coef       0.087(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0402
_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/[\s^2^(Fo^2^)+(0.0552P)^2^+0.0599P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1093
_reflns_number_gt                759
_reflns_number_total             944
_reflns_threshold_expression     I>2\s(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_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
_atom_site_type_symbol
O1 1.1837(2) 0.2500 0.67936(18) 0.0607(5) Uani d S 1 O
O2 0.9826(2) 0.2500 0.37424(16) 0.0548(4) Uani d S 1 O
O3 0.3322(2) 0.2500 0.17084(18) 0.0756(6) Uani d S 1 O
N1 0.8331(2) 0.2500 0.57448(17) 0.0397(4) Uani d S 1 N
N2 0.6286(2) 0.2500 0.59470(18) 0.0416(4) Uani d S 1 N
N3 0.6193(2) 0.2500 0.35833(17) 0.0386(4) Uani d S 1 N
C1 1.0092(3) 0.2500 0.6965(2) 0.0435(5) Uani d S 1 C
C2 0.9545(3) 0.2500 0.8395(2) 0.0604(6) Uani d S 1 C
H2A 0.8627 0.3691 0.8435 0.091 Uiso calc PR 0.50 H
H2B 1.0804 0.2636 0.9167 0.091 Uiso calc PR 0.50 H
H2C 0.8850 0.1173 0.8510 0.091 Uiso calc PR 0.50 H
C3 0.5092(3) 0.2500 0.4656(2) 0.0395(5) Uani d S 1 C
H3 0.3633 0.2500 0.4454 0.047 Uiso calc SR 1 H
C4 0.5205(3) 0.2500 0.2067(2) 0.0477(5) Uani d S 1 C
C5 0.8350(3) 0.2500 0.4286(2) 0.0392(4) Uani d S 1 C
C6 0.6558(4) 0.2500 0.1041(2) 0.0670(7) Uani d S 1 C
H6A 0.7701 0.1510 0.1377 0.100 Uiso calc PR 0.50 H
H6B 0.7106 0.3924 0.0985 0.100 Uiso calc PR 0.50 H
H6C 0.5751 0.2065 0.0092 0.100 Uiso calc PR 0.50 H
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
O1 0.0280(7) 0.0870(12) 0.0635(10) 0.000 0.0050(6) 0.000
O2 0.0345(7) 0.0772(11) 0.0572(9) 0.000 0.0202(6) 0.000
O3 0.0426(9) 0.1226(17) 0.0541(10) 0.000 -0.0018(7) 0.000
N1 0.0251(7) 0.0501(9) 0.0435(9) 0.000 0.0081(6) 0.000
N2 0.0250(7) 0.0514(10) 0.0503(9) 0.000 0.0133(6) 0.000
N3 0.0287(7) 0.0437(9) 0.0421(9) 0.000 0.0064(6) 0.000
C1 0.0302(9) 0.0498(11) 0.0475(11) 0.000 0.0041(8) 0.000
C2 0.0456(11) 0.0862(17) 0.0458(12) 0.000 0.0048(9) 0.000
C3 0.0268(8) 0.0432(10) 0.0483(11) 0.000 0.0090(8) 0.000
C4 0.0433(10) 0.0532(12) 0.0424(11) 0.000 0.0029(8) 0.000
C5 0.0287(8) 0.0421(10) 0.0466(10) 0.000 0.0088(7) 0.000
C6 0.0626(15) 0.094(2) 0.0443(12) 0.000 0.0132(11) 0.000
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
_geom_angle_publ_flag
C5 N1 N2 112.62(14) y
C5 N1 C1 127.14(15) y
N2 N1 C1 120.23(16) y
C3 N2 N1 104.40(15) y
C3 N3 C5 107.66(15) y
C3 N3 C4 123.37(15) y
C5 N3 C4 128.97(17) y
O1 C1 N1 120.29(19) y
O1 C1 C2 125.60(19) y
N1 C1 C2 114.11(16) y
C1 C2 H2A 109.5 ?
C1 C2 H2B 109.5 ?
H2A C2 H2B 109.5 ?
C1 C2 H2C 109.5 ?
H2A C2 H2C 109.5 ?
H2B C2 H2C 109.5 ?
N2 C3 N3 113.14(15) y
N2 C3 H3 123.4 ?
N3 C3 H3 123.4 ?
O3 C4 N3 117.6(2) y
O3 C4 C6 124.4(2) y
N3 C4 C6 117.92(18) y
O2 C5 N1 129.41(17) y
O2 C5 N3 128.42(18) y
N1 C5 N3 102.17(15) y
C4 C6 H6A 109.5 ?
C4 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C4 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.198(2) y
O2 C5 1.206(2) y
O3 C4 1.198(3) y
N1 C5 1.384(3) y
N1 N2 1.405(2) y
N1 C1 1.415(2) y
N2 C3 1.276(2) y
N3 C3 1.386(2) y
N3 C5 1.406(2) y
N3 C4 1.419(3) y
C1 C2 1.485(3) y
C2 H2A 0.9600 ?
C2 H2B 0.9600 ?
C2 H2C 0.9600 ?
C3 H3 0.9300 ?
C4 C6 1.472(3) y
C6 H6A 0.9600 ?
C6 H6B 0.9600 ?
C6 H6C 0.9600 ?
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
C3 H3 O2 1_455 0.93 2.42 3.350(3) 175.8
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
_geom_torsion_publ_flag
C5 N1 N2 C3 0.0 ?
C1 N1 N2 C3 180.0 ?
C5 N1 C1 O1 0.0 y
N2 N1 C1 O1 180.0 y
C5 N1 C1 C2 180.0 y
N2 N1 C1 C2 0.0 y
N1 N2 C3 N3 0.0 ?
C5 N3 C3 N2 0.0 ?
C4 N3 C3 N2 180.0 ?
C3 N3 C4 O3 0.0 y
C5 N3 C4 O3 180.0 y
C3 N3 C4 C6 180.0 y
C5 N3 C4 C6 0.0 y
N2 N1 C5 O2 180.0 ?
C1 N1 C5 O2 0.0 ?
N2 N1 C5 N3 0.0 ?
C1 N1 C5 N3 180.0 ?
C3 N3 C5 O2 180.0 ?
C4 N3 C5 O2 0.0 ?
C3 N3 C5 N1 0.0 ?
C4 N3 C5 N1 180.0 ?
_cod_database_code 2203315
_cod_database_fobs_code 2203315
