#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/32/2223240.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_2223240
loop_
_publ_author_name
'Zemama, Redwan Mohamed'
'Amari, Ibtissam'
'Bouhfid, Rachid'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
6-Methyl-7,7,9-tripropargyl-7H-1,2,4-triazolo[4,3-b][1,2,4]triazepin-8(9H)-one
_journal_coeditor_code           XU2584
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2148
_journal_paper_doi               10.1107/S1600536809031341
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H13 N5 O'
_chemical_formula_moiety         'C15 H13 N5 O'
_chemical_formula_sum            'C15 H13 N5 O'
_chemical_formula_weight         279.30
_chemical_name_systematic
;
6-Methyl-7,7,9-tripropargyl-7H-1,2,4-
triazolo[4,3-b][1,2,4]triazepin-8(9H)-one
;
_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                108.5100(10)
_cell_angle_beta                 90.6590(10)
_cell_angle_gamma                114.7260(10)
_cell_formula_units_Z            2
_cell_length_a                   7.6710(2)
_cell_length_b                   8.2415(2)
_cell_length_c                   12.9619(3)
_cell_measurement_reflns_used    6818
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.3
_cell_measurement_theta_min      2.8
_cell_volume                     695.85(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16879
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0758P)²+0.0861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1292
_reflns_number_gt                2577
_reflns_number_total             3187
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2584.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2223240
_cod_database_fobs_code          2223240
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
O O1 0.30213(18) 0.47985(14) 0.37303(8) 0.0488(3) Uani d . 1 . .
N N1 0.07241(16) -0.03916(15) 0.11746(9) 0.0346(3) Uani d . 1 . .
N N2 0.22767(16) 0.05768(15) 0.07150(8) 0.0323(3) Uani d . 1 . .
N N3 0.4030(2) 0.1070(2) -0.05735(10) 0.0462(3) Uani d . 1 . .
N N4 0.46123(19) 0.28152(18) 0.02864(10) 0.0446(3) Uani d . 1 . .
N N5 0.35151(17) 0.38407(15) 0.19840(9) 0.0372(3) Uani d . 1 . .
C C1 0.31447(19) 0.35728(17) 0.29631(11) 0.0330(3) Uani d . 1 . .
C C2 0.28282(18) 0.16329(17) 0.30330(10) 0.0289(3) Uani d . 1 . .
C C3 0.09422(18) 0.01262(17) 0.22312(10) 0.0303(3) Uani d . 1 . .
C C4 -0.0871(2) -0.0827(2) 0.26582(13) 0.0475(4) Uani d . 1 . .
H H4A -0.1893 -0.1748 0.2049 0.071 Uiso calc R 1 . .
H H4B -0.1255 0.0114 0.3090 0.071 Uiso calc R 1 . .
H H4C -0.0628 -0.1461 0.3109 0.071 Uiso calc R 1 . .
C C5 0.45567(18) 0.11327(18) 0.27425(11) 0.0317(3) Uani d . 1 . .
H H5A 0.4502 0.0191 0.3055 0.038 Uiso calc R 1 . .
H H5B 0.4400 0.0560 0.1947 0.038 Uiso calc R 1 . .
C C6 0.6465(2) 0.2779(2) 0.31450(12) 0.0412(3) Uani d . 1 . .
C C7 0.8004(3) 0.4075(3) 0.34405(18) 0.0702(5) Uani d . 1 . .
H H7 0.9233 0.5109 0.3676 0.084 Uiso calc R 1 . .
C C8 0.2658(2) 0.18290(19) 0.42552(11) 0.0372(3) Uani d . 1 . .
H H8A 0.3796 0.2944 0.4728 0.045 Uiso calc R 1 . .
H H8B 0.1525 0.2037 0.4431 0.045 Uiso calc R 1 . .
C C9 0.2492(2) 0.0156(2) 0.44969(11) 0.0398(3) Uani d . 1 . .
C C10 0.2456(2) -0.1166(2) 0.46867(14) 0.0512(4) Uani d . 1 . .
H H10 0.2427 -0.2208 0.4836 0.061 Uiso calc R 1 . .
C C11 0.2649(2) -0.0213(2) -0.03028(11) 0.0401(3) Uani d . 1 . .
H H11 0.1996 -0.1499 -0.0742 0.048 Uiso calc R 1 . .
C C12 0.3531(2) 0.24704(19) 0.10322(11) 0.0343(3) Uani d . 1 . .
C C13 0.3765(2) 0.56697(19) 0.18940(13) 0.0451(4) Uani d . 1 . .
H H13A 0.4427 0.6700 0.2593 0.054 Uiso calc R 1 . .
H H13B 0.4564 0.5933 0.1338 0.054 Uiso calc R 1 . .
C C14 0.1885(3) 0.5585(2) 0.15971(13) 0.0482(4) Uani d . 1 . .
C C15 0.0358(3) 0.5466(3) 0.13320(17) 0.0655(5) Uani d . 1 . .
H H15 -0.0853 0.5372 0.1122 0.079 Uiso calc R 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
C3 N1 N2 . . 117.64(11) ?
C12 N2 C11 . . 104.18(11) ?
C12 N2 N1 . . 130.86(11) ?
C11 N2 N1 . . 124.18(11) ?
C11 N3 N4 . . 107.51(11) ?
C12 N4 N3 . . 106.47(12) ?
C1 N5 C12 . . 124.97(10) ?
C1 N5 C13 . . 118.17(11) ?
C12 N5 C13 . . 116.66(11) ?
O1 C1 N5 . . 120.67(11) ?
O1 C1 C2 . . 121.75(12) ?
N5 C1 C2 . . 117.55(10) ?
C3 C2 C1 . . 106.03(10) ?
C3 C2 C8 . . 112.84(10) ?
C1 C2 C8 . . 105.71(10) ?
C3 C2 C5 . . 110.77(10) ?
C1 C2 C5 . . 113.58(10) ?
C8 C2 C5 . . 107.91(10) ?
N1 C3 C4 . . 113.98(12) ?
N1 C3 C2 . . 125.47(11) ?
C4 C3 C2 . . 120.51(11) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C6 C5 C2 . . 113.64(11) ?
C6 C5 H5A . . 108.8 ?
C2 C5 H5A . . 108.8 ?
C6 C5 H5B . . 108.8 ?
C2 C5 H5B . . 108.8 ?
H5A C5 H5B . . 107.7 ?
C7 C6 C5 . . 178.18(18) ?
C6 C7 H7 . . 180.0 ?
C9 C8 C2 . . 113.42(11) ?
C9 C8 H8A . . 108.9 ?
C2 C8 H8A . . 108.9 ?
C9 C8 H8B . . 108.9 ?
C2 C8 H8B . . 108.9 ?
H8A C8 H8B . . 107.7 ?
C10 C9 C8 . . 176.60(16) ?
C9 C10 H10 . . 180.0 ?
N3 C11 N2 . . 110.81(13) ?
N3 C11 H11 . . 124.6 ?
N2 C11 H11 . . 124.6 ?
N4 C12 N2 . . 111.01(12) ?
N4 C12 N5 . . 125.45(12) ?
N2 C12 N5 . . 123.34(11) ?
C14 C13 N5 . . 110.59(12) ?
C14 C13 H13A . . 109.5 ?
N5 C13 H13A . . 109.5 ?
C14 C13 H13B . . 109.5 ?
N5 C13 H13B . . 109.5 ?
H13A C13 H13B . . 108.1 ?
C15 C14 C13 . . 178.00(18) ?
C14 C15 H15 . . 180.0 ?
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
O1 C1 . 1.2094(15) ?
N1 C3 . 1.2845(17) ?
N1 N2 . 1.3905(15) ?
N2 C12 . 1.3630(17) ?
N2 C11 . 1.3653(17) ?
N3 C11 . 1.293(2) ?
N3 N4 . 1.3940(18) ?
N4 C12 . 1.3035(17) ?
N5 C1 . 1.3690(17) ?
N5 C12 . 1.3874(17) ?
N5 C13 . 1.4808(16) ?
C1 C2 . 1.5463(16) ?
C2 C3 . 1.5357(17) ?
C2 C8 . 1.5532(17) ?
C2 C5 . 1.5620(17) ?
C3 C4 . 1.4957(19) ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 C6 . 1.4583(19) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.165(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.4643(19) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.180(2) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C13 C14 . 1.455(2) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.172(3) ?
C15 H15 . 0.9300 ?
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
C3 N1 N2 C12 . . . . -40.63(18) ?
C3 N1 N2 C11 . . . . 151.13(13) ?
C11 N3 N4 C12 . . . . 0.01(16) ?
C12 N5 C1 O1 . . . . -174.64(13) ?
C13 N5 C1 O1 . . . . 0.2(2) ?
C12 N5 C1 C2 . . . . 3.4(2) ?
C13 N5 C1 C2 . . . . 178.27(11) ?
O1 C1 C2 C3 . . . . 112.39(14) ?
N5 C1 C2 C3 . . . . -65.67(14) ?
O1 C1 C2 C8 . . . . -7.63(17) ?
N5 C1 C2 C8 . . . . 174.31(12) ?
O1 C1 C2 C5 . . . . -125.74(14) ?
N5 C1 C2 C5 . . . . 56.20(15) ?
N2 N1 C3 C4 . . . . 173.10(11) ?
N2 N1 C3 C2 . . . . -4.67(18) ?
C1 C2 C3 N1 . . . . 68.84(15) ?
C8 C2 C3 N1 . . . . -175.91(12) ?
C5 C2 C3 N1 . . . . -54.80(16) ?
C1 C2 C3 C4 . . . . -108.79(13) ?
C8 C2 C3 C4 . . . . 6.46(16) ?
C5 C2 C3 C4 . . . . 127.57(13) ?
C3 C2 C5 C6 . . . . 156.96(11) ?
C1 C2 C5 C6 . . . . 37.77(15) ?
C8 C2 C5 C6 . . . . -79.06(13) ?
C3 C2 C8 C9 . . . . 68.72(15) ?
C1 C2 C8 C9 . . . . -175.83(11) ?
C5 C2 C8 C9 . . . . -53.99(15) ?
C2 C8 C9 C10 . . . . 72(3) ?
N4 N3 C11 N2 . . . . -0.81(16) ?
C12 N2 C11 N3 . . . . 1.25(15) ?
N1 N2 C11 N3 . . . . 172.10(11) ?
N3 N4 C12 N2 . . . . 0.80(15) ?
N3 N4 C12 N5 . . . . -174.12(12) ?
C11 N2 C12 N4 . . . . -1.25(15) ?
N1 N2 C12 N4 . . . . -171.23(12) ?
C11 N2 C12 N5 . . . . 173.80(12) ?
N1 N2 C12 N5 . . . . 3.8(2) ?
C1 N5 C12 N4 . . . . -148.84(14) ?
C13 N5 C12 N4 . . . . 36.3(2) ?
C1 N5 C12 N2 . . . . 36.8(2) ?
C13 N5 C12 N2 . . . . -138.05(13) ?
C1 N5 C13 C14 . . . . -84.87(17) ?
C12 N5 C13 C14 . . . . 90.39(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743047
