##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2014-11-16
_journal_date_accepted     2014-11-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      1
_journal_page_first     o1
_journal_page_last     o2
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989014025687
_journal_coeditor_code     RZ5141
_publ_contact_author_name     'Abdellah Harmaoui'
_publ_contact_author_address
;
Laboratoire de Chimie Organique Hétérocyclique URAC 21, Pharmacochimie,
Av Ibn Battouta, BP 1014, Faculté  des Sciences,
Université Mohammed V-Agdal, Rabat, Morocco
;
_publ_contact_author_email     'a_harmaoui@yahoo.fr'
_publ_contact_author_fax     '212 537 77 54 40'
_publ_contact_author_phone     '212 537 77 54 40'
_publ_section_title
;\
Crystal structure of
6,9-dimethyl-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazepin-\
8(9H)-one 0.40-hydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Harmaoui, Abdellah'
;
Laboratoire de Chimie Organique Hétérocyclique URAC 21,
Pôle de Compétences Pharmacochimie, Av. Ibn Battouta, BP 1014,
Faculté des Sciences, Université Mohammed V, Rabat, Morocco
;
    'Bouhfid, Rachid'
;
Moroccan Foundation for Advanced Science, Innovation and Research (MASCIR),
Rabat, Morocco
;
    'Essassi, El Mokhtar'
;
Laboratoire de Chimie Organique Hétérocyclique URAC 21,
Pôle de Compétences Pharmacochimie, Av. Ibn Battouta, BP 1014,
Faculté des Sciences, Université Mohammed V, Rabat, Morocco
Moroccan Foundation for Advanced Science, Innovation and Research (MASCIR),
Rabat, Morocco
;
    'Saadi, Mohamed'
;
Laboratoire de Chimie du Solide Appliquée,
Faculté des Sciences, Université Mohammed V
Avenue Ibn Battouta, BP 1014, Rabat, Morocco
;
    'El Ammari, Lahcen'
;
Laboratoire de Chimie du Solide Appliquée,
Faculté des Sciences, Université Mohammed V
Avenue Ibn Battouta, BP 1014, Rabat, Morocco
;
_database_code_depnum_ccdc_archive     'CCDC 1035668'
_chemical_name_systematic
;\
6,9-Dimethyl-7H-[1,2,4]triazolo[4,3-b]\
[1,2,4]triazepin-8(9H)-one 0.40-hydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C7 H9 N5 O, 0.4(H2 O)'
_chemical_formula_sum     'C7 H9.80 N5 O1.40'
_chemical_formula_iupac     'C7 H9 N5 O, 0.4H2 O'
_chemical_formula_weight     186.44
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     11.4970(18)
_cell_length_b     11.4527(18)
_cell_length_c     14.867(2)
_cell_angle_alpha     90.00
_cell_angle_beta     109.615(4)
_cell_angle_gamma     90.00
_cell_volume     1843.9(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2039
_cell_measurement_theta_min     2.59
_cell_measurement_theta_max     27.10
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.34
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.343
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     784
_exptl_absorpt_coefficient_mu     0.100
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_absorpt_correction_T_min     0.6373
_exptl_absorpt_correction_T_max     0.7464
_exptl_special_details     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker X8 APEX'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_reflns_number     14175
_diffrn_reflns_av_R_equivalents     0.0328
_diffrn_reflns_av_sigmaI/netI     0.0187
_diffrn_reflns_theta_min     2.59
_diffrn_reflns_theta_max     27.10
_diffrn_reflns_theta_full     27.10
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_refine_special_details
;
Refinement of F² against all reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on all data will be
even larger.
;
_reflns_number_total     2039
_reflns_number_gt     1600
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0556
_refine_ls_R_factor_gt     0.0424
_refine_ls_wR_factor_gt     0.1126
_refine_ls_wR_factor_ref     0.1246
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     2039
_refine_ls_number_parameters     123
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0565P)²+1.2827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.278
_refine_diff_density_min     -0.195
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2009)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2009)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2009) and publCIF (Westrip,2010)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.33958(13) 0.65257(14) 0.16698(10) 0.0369(3) Uani d . 1 1 . .
    C C2 0.34033(16) 0.52181(14) 0.16066(11) 0.0433(4) Uani d . 1 1 . .
    H H2A 0.4176 0.4962 0.1544 0.052 Uiso calc R 1 1 . .
    H H2B 0.3344 0.4885 0.2190 0.052 Uiso calc R 1 1 . .
    C C3 0.23480(17) 0.47878(14) 0.07690(12) 0.0476(4) Uani d . 1 1 . .
    C C4 0.33342(14) 0.57338(13) -0.02393(10) 0.0362(3) Uani d . 1 1 . .
    C C5 0.46928(15) 0.70820(15) -0.00967(12) 0.0453(4) Uani d . 1 1 . .
    H H5 0.5204 0.7725 0.0124 0.054 Uiso calc R 1 1 . .
    C C6 0.30729(19) 0.70739(19) 0.24624(12) 0.0571(5) Uani d . 1 1 . .
    H H6A 0.3102 0.7908 0.2412 0.086 Uiso calc R 1 1 . .
    H H6B 0.3652 0.6828 0.3063 0.086 Uiso calc R 1 1 . .
    H H6C 0.2256 0.6839 0.2424 0.086 Uiso calc R 1 1 . .
    C C7 0.1424(2) 0.4639(2) -0.09733(15) 0.0758(7) Uani d . 1 1 . .
    H H7A 0.1563 0.4934 -0.1533 0.114 Uiso calc R 1 1 . .
    H H7B 0.0623 0.4881 -0.0976 0.114 Uiso calc R 1 1 . .
    H H7C 0.1464 0.3802 -0.0970 0.114 Uiso calc R 1 1 . .
    N N1 0.23754(13) 0.50997(12) -0.01151(9) 0.0445(4) Uani d . 1 1 . .
    N N2 0.37481(14) 0.56109(13) -0.09512(10) 0.0478(4) Uani d . 1 1 . .
    N N3 0.46286(14) 0.64862(14) -0.08511(10) 0.0508(4) Uani d . 1 1 . .
    N N4 0.39103(11) 0.66406(11) 0.03305(8) 0.0346(3) Uani d . 1 1 . .
    N N5 0.36603(12) 0.72045(11) 0.10833(9) 0.0388(3) Uani d . 1 1 . .
    O O1 0.15060(15) 0.42096(14) 0.08579(11) 0.0790(5) Uani d . 1 1 . .
    O O2 0.5000 0.7639(2) -0.2500 0.0618(6) Uani d SP 0.80 2 . .
    H H1 0.5068 0.7196 -0.2959 0.093 Uiso d PR 0.80 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
    C1 0.0326(7) 0.0460(8) 0.0320(7) 0.0009(6) 0.0109(6) -0.0009(6)
    C2 0.0514(9) 0.0455(9) 0.0367(8) 0.0024(7) 0.0195(7) 0.0089(7)
    C3 0.0595(10) 0.0394(9) 0.0497(9) -0.0114(7) 0.0260(8) 0.0005(7)
    C4 0.0434(8) 0.0345(7) 0.0327(7) -0.0018(6) 0.0153(6) 0.0007(6)
    C5 0.0470(9) 0.0483(9) 0.0455(9) -0.0091(7) 0.0221(7) 0.0049(7)
    C6 0.0644(11) 0.0709(12) 0.0426(9) 0.0104(10) 0.0265(9) -0.0051(9)
    C7 0.0784(15) 0.0916(16) 0.0559(12) -0.0408(13) 0.0204(11) -0.0244(11)
    N1 0.0507(8) 0.0441(7) 0.0390(7) -0.0160(6) 0.0157(6) -0.0057(6)
    N2 0.0624(9) 0.0490(8) 0.0380(7) -0.0019(7) 0.0247(7) -0.0020(6)
    N3 0.0572(9) 0.0588(9) 0.0451(8) -0.0025(7) 0.0287(7) 0.0055(7)
    N4 0.0393(7) 0.0348(6) 0.0332(6) -0.0042(5) 0.0166(5) -0.0007(5)
    N5 0.0427(7) 0.0383(7) 0.0369(6) -0.0023(5) 0.0154(5) -0.0066(5)
    O1 0.0913(11) 0.0827(11) 0.0718(10) -0.0466(9) 0.0389(9) -0.0012(8)
    O2 0.0912(18) 0.0554(13) 0.0507(13) 0.000 0.0395(13) 0.000
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    C1 N5 . 1.2788(19) ?
    C1 C6 . 1.488(2) ?
    C1 C2 . 1.501(2) ?
    C2 C3 . 1.500(2) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 O1 . 1.216(2) ?
    C3 N1 . 1.373(2) ?
    C4 N2 . 1.306(2) ?
    C4 N4 . 1.3632(19) ?
    C4 N1 . 1.383(2) ?
    C5 N3 . 1.294(2) ?
    C5 N4 . 1.3610(19) ?
    C5 H5 . 0.9300 ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C7 N1 . 1.472(2) ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    N2 N3 . 1.397(2) ?
    N4 N5 . 1.4029(17) ?
    O2 H1 . 0.8745 ?
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
    N5 C1 C6 . . 117.59(15) ?
    N5 C1 C2 . . 123.80(14) ?
    C6 C1 C2 . . 118.61(14) ?
    C3 C2 C1 . . 111.08(13) ?
    C3 C2 H2A . . 109.4 ?
    C1 C2 H2A . . 109.4 ?
    C3 C2 H2B . . 109.4 ?
    C1 C2 H2B . . 109.4 ?
    H2A C2 H2B . . 108.0 ?
    O1 C3 N1 . . 121.38(17) ?
    O1 C3 C2 . . 122.69(16) ?
    N1 C3 C2 . . 115.92(14) ?
    N2 C4 N4 . . 110.65(13) ?
    N2 C4 N1 . . 125.12(14) ?
    N4 C4 N1 . . 124.04(13) ?
    N3 C5 N4 . . 110.76(15) ?
    N3 C5 H5 . . 124.6 ?
    N4 C5 H5 . . 124.6 ?
    C1 C6 H6A . . 109.5 ?
    C1 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C1 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    N1 C7 H7A . . 109.5 ?
    N1 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    N1 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    C3 N1 C4 . . 122.68(14) ?
    C3 N1 C7 . . 119.17(15) ?
    C4 N1 C7 . . 117.80(14) ?
    C4 N2 N3 . . 106.54(13) ?
    C5 N3 N2 . . 107.42(13) ?
    C5 N4 C4 . . 104.61(13) ?
    C5 N4 N5 . . 123.08(13) ?
    C4 N4 N5 . . 131.27(12) ?
    C1 N5 N4 . . 115.05(13) ?
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
    C2 H2A N3 5_665 0.97 2.58 3.449(3) 149
    C5 H5 O1 3_555 0.93 2.29 3.211(2) 173
    O2 H1 N3 2_654 0.87 2.08 2.939(2) 167
_iucr_refine_instructions_details
;
TITL EL14_D232_DRX2 in C2/c
CELL  0.71073  11.4970  11.4527  14.8667   90.000  109.615   90.000
ZERR     8.00   0.0018   0.0018   0.0024    0.000    0.004    0.000
LATT   7
SYMM  - X,   Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  56   78.4   40   11.2
MERG   2
SHEL 50 0.78
HTAB O2 N3_$1
HTAB C5 O1_$2
eqiv $1 1-x, y, -z-1/2
eqiv $2 x+1/2, y+1/2, z
FMAP   2
PLAN   10
ACTA
BOND
BOND   $H
HTAB 2.6
L.S.  10
TEMP    23.00
rem EXTI    0.001448
WGHT      0.0565      1.2827
FVAR       0.46058
C1    1    0.339579    0.652571    0.166981    11.00000    0.03259    0.04602 =
         0.03200   -0.00086    0.01086    0.00086
C2    1    0.340327    0.521811    0.160660    11.00000    0.05136    0.04546 =
         0.03670    0.00893    0.01949    0.00244
AFIX  23
H2A   2    0.417645    0.496202    0.154357    11.00000   -1.20000
H2B   2    0.334365    0.488536    0.218955    11.00000   -1.20000
AFIX   0
C3    1    0.234796    0.478783    0.076900    11.00000    0.05950    0.03935 =
         0.04973    0.00052    0.02601   -0.01137
C4    1    0.333420    0.573381   -0.023935    11.00000    0.04341    0.03449 =
         0.03267    0.00074    0.01528   -0.00179
C5    1    0.469284    0.708205   -0.009673    11.00000    0.04703    0.04835 =
         0.04546    0.00489    0.02212   -0.00911
AFIX  43
H5    2    0.520406    0.772452    0.012361    11.00000   -1.20000
AFIX   0
C6    1    0.307292    0.707395    0.246237    11.00000    0.06434    0.07095 =
         0.04256   -0.00514    0.02651    0.01036
AFIX  33
H6A   2    0.310205    0.790831    0.241168    11.00000   -1.50000
H6B   2    0.365252    0.682813    0.306323    11.00000   -1.50000
H6C   2    0.225590    0.683912    0.242353    11.00000   -1.50000
AFIX   0
C7    1    0.142354    0.463898   -0.097338    11.00000    0.07845    0.09163 =
         0.05588   -0.02439    0.02047   -0.04078
AFIX  33
H7A   2    0.156309    0.493376   -0.153304    11.00000   -1.50000
H7B   2    0.062279    0.488104   -0.097645    11.00000   -1.50000
H7C   2    0.146394    0.380168   -0.097043    11.00000   -1.50000
AFIX   0
N1    3    0.237542    0.509968   -0.011507    11.00000    0.05072    0.04412 =
         0.03902   -0.00567    0.01573   -0.01597
N2    3    0.374810    0.561089   -0.095123    11.00000    0.06238    0.04901 =
         0.03798   -0.00200    0.02468   -0.00186
N3    3    0.462862    0.648616   -0.085112    11.00000    0.05720    0.05876 =
         0.04514    0.00549    0.02872   -0.00249
N4    3    0.391029    0.664061    0.033055    11.00000    0.03926    0.03481 =
         0.03321   -0.00070    0.01658   -0.00420
N5    3    0.366030    0.720454    0.108330    11.00000    0.04267    0.03832 =
         0.03687   -0.00662    0.01540   -0.00232
O1    4    0.150604    0.420961    0.085789    11.00000    0.09133    0.08266 =
         0.07176   -0.00124    0.03890   -0.04656
O2    4    0.500000    0.763887   -0.250000    10.40198    0.09127    0.05541 =
         0.05071    0.00000    0.03955    0.00000
AFIX   3
H1    2    0.506763    0.719645   -0.295937    10.80396   -1.50000
HKLF 4
REM  EL14_D232_DRX2 in C2/c
REM R1 =  0.0424 for   1600 Fo > 4sig(Fo)  and  0.0556 for all   2039 data
REM    123 parameters refined using      0 restraints
END
WGHT      0.0565      1.2827
REM Highest difference peak  0.278,  deepest hole -0.195,  1-sigma level  0.038
Q1    1   0.0450  0.4847 -0.1702  11.00000  0.05    0.28
Q2    1   0.1058  0.5400 -0.1507  11.00000  0.05    0.21
Q3    1   0.0958  0.4540  0.0273  11.00000  0.05    0.18
Q4    1   0.0683  0.4282 -0.0751  11.00000  0.05    0.18
Q5    1   0.4386  0.7297 -0.2811  11.00000  0.05    0.17
Q6    1   0.3336  0.5902  0.1615  11.00000  0.05    0.17
Q7    1   0.3388  0.6458  0.3106  11.00000  0.05    0.16
Q8    1   0.2790  0.5193  0.1151  11.00000  0.05    0.16
Q9    1   0.3670  0.7874  0.2748  11.00000  0.05    0.13
Q10   1   0.5000  0.8170 -0.2500  10.50000  0.05    0.13
;
