#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/39/2223926.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_2223926
loop_
_publ_author_name
'Dutkiewicz, Grzegorz'
'Chidan Kumar, C. S.'
'Yathirajan, H. S.'
'Mayekar, A. N.'
'Kubicki, Maciej'
_publ_section_title
;
 3-Methyl-1,2,4-triazolo[3,4-a]phthalazine monohydrate
;
_journal_coeditor_code           NC2160
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2694
_journal_paper_doi               10.1107/S1600536809040677
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H8 N4, H2 O'
_chemical_formula_moiety         'C10 H8 N4, H2 O'
_chemical_formula_sum            'C10 H10 N4 O'
_chemical_formula_weight         202.22
_chemical_name_systematic
;
3-Methyl-1,2,4-triazolo[3,4-a]phthalazine monohydrate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.663(10)
_cell_angle_beta                 104.910(10)
_cell_angle_gamma                95.830(9)
_cell_formula_units_Z            2
_cell_length_a                   7.3009(9)
_cell_length_b                   7.9253(9)
_cell_length_c                   9.2755(10)
_cell_measurement_reflns_used    2647
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      75.6171
_cell_measurement_theta_min      6.3992
_cell_volume                     477.83(11)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'XP (Siemens, 1989)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 5.2679
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova (single source at offset) Atlas'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2893
_diffrn_reflns_theta_full        69.98
_diffrn_reflns_theta_max         69.98
_diffrn_reflns_theta_min         6.41
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0567
_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)+(0.07P)²+0.128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1471
_reflns_number_gt                1615
_reflns_number_total             1772
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2160.cif
_cod_data_source_block           I
_cod_original_cell_volume        477.83(10)
_cod_database_code               2223926
_cod_database_fobs_code          2223926
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.0820(2) 0.4413(2) 0.25290(18) 0.0576(5) Uani d . 1 . .
N N2 -0.0116(2) 0.2599(2) 0.16838(18) 0.0585(5) Uani d . 1 . .
C C3 0.0258(2) 0.1699(3) 0.2642(2) 0.0504(4) Uani d . 1 . .
C C31 -0.0377(3) -0.0275(3) 0.2252(2) 0.0629(5) Uani d . 1 . .
H H31A -0.1301 -0.0825 0.1193 0.094 Uiso d R 1 . .
H H31B -0.0966 -0.0436 0.3024 0.094 Uiso d R 1 . .
H H31C 0.0722 -0.0847 0.2287 0.094 Uiso d R 1 . .
N N4 0.1420(2) 0.2902(2) 0.41193(16) 0.0455(4) Uani d . 1 . .
N N5 0.2127(2) 0.2489(2) 0.54647(17) 0.0530(4) Uani d . 1 . .
C C6 0.3218(3) 0.3879(3) 0.6698(2) 0.0533(5) Uani d . 1 . .
H H6 0.372(3) 0.360(3) 0.765(3) 0.070(6) Uiso d . 1 . .
C C7 0.3736(2) 0.5716(2) 0.6764(2) 0.0477(4) Uani d . 1 . .
C C8 0.4993(3) 0.7118(3) 0.8151(2) 0.0562(5) Uani d . 1 . .
H H8 0.557(4) 0.683(3) 0.913(3) 0.080(7) Uiso d . 1 . .
C C9 0.5466(3) 0.8835(3) 0.8153(3) 0.0600(5) Uani d . 1 . .
H H9 0.636(3) 0.978(3) 0.909(3) 0.067(6) Uiso d . 1 . .
C C10 0.4682(3) 0.9207(3) 0.6786(3) 0.0613(5) Uani d . 1 . .
H H10 0.506(4) 1.043(4) 0.685(3) 0.080(7) Uiso d . 1 . .
C C11 0.3434(3) 0.7866(3) 0.5412(2) 0.0573(5) Uani d . 1 . .
H H11 0.283(3) 0.805(3) 0.447(3) 0.074(7) Uiso d . 1 . .
C C12 0.2970(2) 0.6096(2) 0.5382(2) 0.0467(4) Uani d . 1 . .
C C13 0.1741(2) 0.4575(3) 0.4000(2) 0.0466(4) Uani d . 1 . .
O O1W 0.2725(3) 0.6362(3) 0.0877(2) 0.0876(6) Uani d . 1 . .
H H1W2 0.198(6) 0.571(6) 0.125(5) 0.143(14) Uiso d . 1 . .
H H1W1 0.197(4) 0.662(4) 0.018(4) 0.092(9) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 N1 N2 . . 107.24(15) ?
C3 N2 N1 . . 108.84(14) ?
N2 C3 N4 . . 108.18(16) ?
N2 C3 C31 . . 127.98(17) ?
N4 C3 C31 . . 123.82(16) ?
C3 C31 H31A . . 109.5 ?
C3 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
C3 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
C3 N4 C13 . . 106.81(14) ?
C3 N4 N5 . . 126.01(15) ?
C13 N4 N5 . . 127.18(15) ?
C6 N5 N4 . . 113.22(14) ?
N5 C6 C7 . . 126.56(16) ?
N5 C6 H6 . . 113.6(14) ?
C7 C6 H6 . . 119.8(14) ?
C8 C7 C12 . . 119.14(17) ?
C8 C7 C6 . . 122.10(16) ?
C12 C7 C6 . . 118.75(16) ?
C9 C8 C7 . . 120.13(18) ?
C9 C8 H8 . . 121.1(14) ?
C7 C8 H8 . . 118.7(14) ?
C8 C9 C10 . . 120.41(19) ?
C8 C9 H9 . . 119.8(14) ?
C10 C9 H9 . . 119.8(14) ?
C11 C10 C9 . . 120.85(19) ?
C11 C10 H10 . . 122.1(15) ?
C9 C10 H10 . . 117.0(15) ?
C10 C11 C12 . . 119.35(18) ?
C10 C11 H11 . . 124.5(15) ?
C12 C11 H11 . . 116.2(15) ?
C11 C12 C7 . . 120.10(18) ?
C11 C12 C13 . . 124.20(16) ?
C7 C12 C13 . . 115.70(16) ?
N1 C13 N4 . . 108.93(16) ?
N1 C13 C12 . . 132.48(17) ?
N4 C13 C12 . . 118.57(15) ?
H1W2 O1W H1W1 . . 107(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C13 . 1.312(2) ?
N1 N2 . 1.384(2) ?
N2 C3 . 1.309(2) ?
C3 N4 . 1.365(2) ?
C3 C31 . 1.476(3) ?
C31 H31A . 0.9600 ?
C31 H31B . 0.9600 ?
C31 H31C . 0.9600 ?
N4 C13 . 1.369(2) ?
N4 N5 . 1.3818(18) ?
N5 C6 . 1.289(2) ?
C6 C7 . 1.443(3) ?
C6 H6 . 0.97(2) ?
C7 C8 . 1.398(3) ?
C7 C12 . 1.404(2) ?
C8 C9 . 1.369(3) ?
C8 H8 . 1.01(3) ?
C9 C10 . 1.391(3) ?
C9 H9 . 0.96(2) ?
C10 C11 . 1.370(3) ?
C10 H10 . 0.96(3) ?
C11 C12 . 1.399(3) ?
C11 H11 . 0.94(3) ?
C12 C13 . 1.432(3) ?
O1W H1W2 . 0.92(5) ?
O1W H1W1 . 0.83(3) ?
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
O1W H1W2 N1 . 0.92(5) 2.08(5) 2.987(2) 168(4)
O1W H1W1 N2 2_565 0.83(3) 2.21(3) 3.043(2) 177(3)
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 N1 N2 C3 . . . . -0.4(2) ?
N1 N2 C3 N4 . . . . 0.5(2) ?
N1 N2 C3 C31 . . . . -177.91(17) ?
N2 C3 N4 C13 . . . . -0.45(19) ?
C31 C3 N4 C13 . . . . 178.04(16) ?
N2 C3 N4 N5 . . . . 179.64(14) ?
C31 C3 N4 N5 . . . . -1.9(3) ?
C3 N4 N5 C6 . . . . 178.98(16) ?
C13 N4 N5 C6 . . . . -0.9(2) ?
N4 N5 C6 C7 . . . . -0.6(3) ?
N5 C6 C7 C8 . . . . -177.53(18) ?
N5 C6 C7 C12 . . . . 1.6(3) ?
C12 C7 C8 C9 . . . . 0.0(3) ?
C6 C7 C8 C9 . . . . 179.10(17) ?
C7 C8 C9 C10 . . . . 0.8(3) ?
C8 C9 C10 C11 . . . . -0.4(3) ?
C9 C10 C11 C12 . . . . -0.9(3) ?
C10 C11 C12 C7 . . . . 1.7(3) ?
C10 C11 C12 C13 . . . . -177.70(16) ?
C8 C7 C12 C11 . . . . -1.3(3) ?
C6 C7 C12 C11 . . . . 179.58(15) ?
C8 C7 C12 C13 . . . . 178.19(14) ?
C6 C7 C12 C13 . . . . -0.9(2) ?
N2 N1 C13 N4 . . . . 0.06(19) ?
N2 N1 C13 C12 . . . . 178.52(17) ?
C3 N4 C13 N1 . . . . 0.23(19) ?
N5 N4 C13 N1 . . . . -179.86(14) ?
C3 N4 C13 C12 . . . . -178.47(13) ?
N5 N4 C13 C12 . . . . 1.4(3) ?
C11 C12 C13 N1 . . . . 0.7(3) ?
C7 C12 C13 N1 . . . . -178.71(17) ?
C11 C12 C13 N4 . . . . 179.08(15) ?
C7 C12 C13 N4 . . . . -0.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655926
