#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/00/2240000.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_2240000
loop_
_publ_author_name
'Patil, Siddappa'
'Bugarin, Alejandro'
_publ_section_title
;
 Crystal structure of
 (E)-1,3-dimethyl-2-[(3-nitrophenyl)triaz-2-enylidene]-2,3-dihydro-1H-imidazole
;
_journal_coeditor_code           SU2778
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              224
_journal_page_last               227
_journal_paper_doi               10.1107/S1600536814020698
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C11 H12 N6 O2'
_chemical_formula_moiety         'C11 H12 N6 O2'
_chemical_formula_sum            'C11 H12 N6 O2'
_chemical_formula_weight         260.27
_chemical_name_systematic
(E)-1,3-Dimethyl-2-[(3-nitrophenyl)triaz-2-enylidene]-2,3-dihydro-1H-imidazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 113.6050(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.0377(5)
_cell_length_b                   12.9071(5)
_cell_length_c                   14.2995(5)
_cell_measurement_reflns_used    9007
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      40.06
_cell_measurement_theta_min      3.06
_cell_volume                     2374.09(15)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2013 (Sheldrick, 2008), PLATON (Spek, 2009) and
publcif (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick 2008)
;
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            60704
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         40.646
_diffrn_reflns_theta_min         2.869
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.297
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         14895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0600P)²+0.4222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1281
_reflns_number_gt                10565
_reflns_number_total             14895
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su2778sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2374.08(15)
_cod_database_code               2240000
_cod_database_fobs_code          2240000
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.973
_shelxl_version_number           2.013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_occupancy
O O1 1.41154(5) 0.17070(6) 0.07592(6) 0.02761(14) Uani d 1
O O2 1.35616(5) 0.32803(5) 0.07112(6) 0.02894(15) Uani d 1
N N1 0.69882(5) 0.35407(5) 0.09704(5) 0.01430(10) Uani d 1
N N2 0.74421(5) 0.19273(5) 0.09668(5) 0.01287(10) Uani d 1
N N3 0.86553(5) 0.33461(5) 0.09907(5) 0.01281(10) Uani d 1
N N4 0.93463(4) 0.26313(5) 0.10078(4) 0.01161(9) Uani d 1
N N5 1.01715(5) 0.30405(5) 0.09846(5) 0.01286(10) Uani d 1
N N6 1.34736(5) 0.23387(6) 0.07898(5) 0.01852(12) Uani d 1
C C1 0.64415(5) 0.19428(6) 0.09429(6) 0.01542(12) Uani d 1
H H1 0.6029 0.1354 0.0927 0.019 Uiso calc 1
C C2 0.61618(5) 0.29407(6) 0.09470(6) 0.01605(12) Uani d 1
H H2 0.5519 0.3186 0.0936 0.019 Uiso calc 1
C C3 0.77707(5) 0.29211(5) 0.09821(5) 0.01153(10) Uani d 1
C C4 0.79822(6) 0.09749(6) 0.09254(6) 0.01641(12) Uani d 1
H H4A 0.8149 0.0987 0.0322 0.025 Uiso calc 1
H H4B 0.7535 0.0379 0.0884 0.025 Uiso calc 1
H H4C 0.8626 0.0918 0.1542 0.025 Uiso calc 1
C C5 0.70332(7) 0.46623(6) 0.09997(8) 0.02396(16) Uani d 1
H H5A 0.7448 0.4892 0.1699 0.036 Uiso calc 1
H H5B 0.6328 0.4943 0.0774 0.036 Uiso calc 1
H H5C 0.7354 0.4910 0.0546 0.036 Uiso calc 1
C C6 1.09080(5) 0.22826(5) 0.10102(5) 0.01144(10) Uani d 1
C C7 1.08081(6) 0.12097(5) 0.11242(6) 0.01449(11) Uani d 1
H H7 1.0200 0.0949 0.1180 0.017 Uiso calc 1
C C8 1.15869(6) 0.05259(6) 0.11562(6) 0.01589(12) Uani d 1
H H8 1.1512 -0.0194 0.1249 0.019 Uiso calc 1
C C9 1.24754(6) 0.08873(6) 0.10535(6) 0.01545(12) Uani d 1
H H9 1.3009 0.0426 0.1071 0.019 Uiso calc 1
C C10 1.25535(5) 0.19462(6) 0.09241(5) 0.01371(11) Uani d 1
C C11 1.18020(5) 0.26503(5) 0.09144(5) 0.01285(11) Uani d 1
H H11 1.1893 0.3371 0.0844 0.015 Uiso calc 1
O O3 0.37570(6) 0.04437(6) 0.82832(7) 0.03536(18) Uani d 1
O O4 0.28471(5) 0.17434(6) 0.84106(6) 0.02731(14) Uani d 1
N N7 1.02372(4) 0.23808(5) 0.84318(5) 0.01204(10) Uani d 1
N N8 0.94498(5) 0.37758(5) 0.86112(5) 0.01262(10) Uani d 1
N N9 0.86200(5) 0.20437(5) 0.84779(5) 0.01280(10) Uani d 1
N N10 0.77639(4) 0.25054(5) 0.84548(5) 0.01187(9) Uani d 1
N N11 0.70763(5) 0.18431(5) 0.84484(5) 0.01359(10) Uani d 1
N N12 0.36319(5) 0.13767(6) 0.83579(6) 0.01928(12) Uani d 1
C C12 1.08846(5) 0.32082(6) 0.84914(6) 0.01436(11) Uani d 1
H H12 1.1547 0.3174 0.8459 0.017 Uiso calc 1
C C13 1.03999(6) 0.40748(6) 0.86051(6) 0.01455(12) Uani d 1
H H13 1.0660 0.4762 0.8669 0.017 Uiso calc 1
C C14 0.93575(5) 0.27292(5) 0.85061(5) 0.01114(10) Uani d 1
C C15 1.04585(5) 0.12916(6) 0.83482(6) 0.01494(12) Uani d 1
H H15A 1.0610 0.0946 0.9003 0.022 Uiso calc 1
H H15B 1.1061 0.1231 0.8169 0.022 Uiso calc 1
H H15C 0.9854 0.0964 0.7817 0.022 Uiso calc 1
C C16 0.87328(6) 0.45063(6) 0.87669(7) 0.01784(13) Uani d 1
H H00A 0.8088 0.4537 0.8149 0.027 Uiso calc 1
H H00B 0.9052 0.5195 0.8912 0.027 Uiso calc 1
H H00C 0.8576 0.4277 0.9343 0.027 Uiso calc 1
C C17 0.61624(5) 0.23313(5) 0.84061(5) 0.01230(11) Uani d 1
C C18 0.59905(6) 0.34078(6) 0.83778(6) 0.01640(12) Uani d 1
H H18 0.6516 0.3870 0.8374 0.020 Uiso calc 1
C C19 0.50599(6) 0.37999(6) 0.83552(7) 0.01905(14) Uani d 1
H H19 0.4958 0.4528 0.8338 0.023 Uiso calc 1
C C20 0.42745(6) 0.31436(6) 0.83575(6) 0.01717(13) Uani d 1
H H20 0.3641 0.3410 0.8352 0.021 Uiso calc 1
C C21 0.44519(5) 0.20858(6) 0.83684(6) 0.01418(11) Uani d 1
C C22 0.53703(5) 0.16660(6) 0.83938(6) 0.01394(11) Uani d 1
H H22 0.5461 0.0936 0.8403 0.017 Uiso calc 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
_geom_angle_publ_flag
C3 N1 C2 109.75(6) ?
C3 N1 C5 124.35(6) ?
C2 N1 C5 125.89(6) ?
C3 N2 C1 108.62(6) ?
C3 N2 C4 128.12(6) ?
C1 N2 C4 123.19(6) ?
N4 N3 C3 112.23(6) y
N5 N4 N3 111.84(6) y
N4 N5 C6 111.86(6) y
O1 N6 O2 123.36(7) ?
O1 N6 C10 118.10(7) ?
O2 N6 C10 118.54(7) ?
C2 C1 N2 107.86(6) ?
C2 C1 H1 126.1 ?
N2 C1 H1 126.1 ?
C1 C2 N1 106.98(6) ?
C1 C2 H2 126.5 ?
N1 C2 H2 126.5 ?
N1 C3 N3 119.86(6) ?
N1 C3 N2 106.78(6) ?
N3 C3 N2 133.35(6) ?
N2 C4 H4A 109.5 ?
N2 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
N2 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
N1 C5 H5A 109.5 ?
N1 C5 H5B 109.5 ?
H5A C5 H5B 109.5 ?
N1 C5 H5C 109.5 ?
H5A C5 H5C 109.5 ?
H5B C5 H5C 109.5 ?
C11 C6 C7 118.69(6) ?
C11 C6 N5 115.99(6) ?
C7 C6 N5 125.31(6) ?
C8 C7 C6 120.95(6) ?
C8 C7 H7 119.5 ?
C6 C7 H7 119.5 ?
C7 C8 C9 120.58(7) ?
C7 C8 H8 119.7 ?
C9 C8 H8 119.7 ?
C10 C9 C8 117.72(6) ?
C10 C9 H9 121.1 ?
C8 C9 H9 121.1 ?
C11 C10 C9 123.03(6) ?
C11 C10 N6 118.49(6) ?
C9 C10 N6 118.48(6) ?
C10 C11 C6 119.00(6) ?
C10 C11 H11 120.5 ?
C6 C11 H11 120.5 ?
C14 N7 C12 109.60(6) ?
C14 N7 C15 123.86(6) ?
C12 N7 C15 126.49(6) ?
C14 N8 C13 108.90(6) ?
C14 N8 C16 128.14(6) ?
C13 N8 C16 122.88(6) ?
N10 N9 C14 112.44(6) y
N11 N10 N9 111.74(6) y
N10 N11 C17 111.77(6) y
O3 N12 O4 123.10(7) ?
O3 N12 C21 118.31(6) ?
O4 N12 C21 118.59(7) ?
C13 C12 N7 107.23(6) ?
C13 C12 H12 126.4 ?
N7 C12 H12 126.4 ?
C12 C13 N8 107.52(6) ?
C12 C13 H13 126.2 ?
N8 C13 H13 126.2 ?
N9 C14 N7 119.42(6) ?
N9 C14 N8 133.82(6) ?
N7 C14 N8 106.75(6) ?
N7 C15 H15A 109.5 ?
N7 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
N7 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
N8 C16 H00A 109.5 ?
N8 C16 H00B 109.5 ?
H00A C16 H00B 109.5 ?
N8 C16 H00C 109.5 ?
H00A C16 H00C 109.5 ?
H00B C16 H00C 109.5 ?
C22 C17 C18 118.63(6) ?
C22 C17 N11 115.56(6) ?
C18 C17 N11 125.81(6) ?
C19 C18 C17 120.58(7) ?
C19 C18 H18 119.7 ?
C17 C18 H18 119.7 ?
C18 C19 C20 121.12(7) ?
C18 C19 H19 119.4 ?
C20 C19 H19 119.4 ?
C21 C20 C19 117.42(7) ?
C21 C20 H20 121.3 ?
C19 C20 H20 121.3 ?
C22 C21 C20 123.12(7) ?
C22 C21 N12 118.34(6) ?
C20 C21 N12 118.55(6) ?
C21 C22 C17 119.12(6) ?
C21 C22 H22 120.4 ?
C17 C22 H22 120.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N6 1.2288(9) ?
O2 N6 1.2313(10) ?
N1 C3 1.3534(9) ?
N1 C2 1.3841(9) ?
N1 C5 1.4489(10) ?
N2 C3 1.3603(9) ?
N2 C1 1.3914(9) ?
N2 C4 1.4578(9) ?
N3 C3 1.3532(9) y
N3 N4 1.3318(8) y
N4 N5 1.2856(8) y
N5 C6 1.4132(9) ?
N6 C10 1.4699(9) ?
C1 C2 1.3473(11) ?
C1 H1 0.9500 ?
C2 H2 0.9500 ?
C4 H4A 0.9800 ?
C4 H4B 0.9800 ?
C4 H4C 0.9800 ?
C5 H5A 0.9800 ?
C5 H5B 0.9800 ?
C5 H5C 0.9800 ?
C6 C11 1.3987(9) ?
C6 C7 1.4078(10) ?
C7 C8 1.3916(10) ?
C7 H7 0.9500 ?
C8 C9 1.3934(10) ?
C8 H8 0.9500 ?
C9 C10 1.3893(10) ?
C9 H9 0.9500 ?
C10 C11 1.3884(10) ?
C11 H11 0.9500 ?
O3 N12 1.2278(10) ?
O4 N12 1.2287(9) ?
N7 C14 1.3578(9) ?
N7 C12 1.3827(9) ?
N7 C15 1.4549(9) ?
N8 C14 1.3597(9) ?
N8 C13 1.3918(9) ?
N8 C16 1.4598(9) ?
N9 C14 1.3501(9) y
N9 N10 1.3299(8) y
N10 N11 1.2866(8) y
N11 C17 1.4087(9) ?
N12 C21 1.4659(10) ?
C12 C13 1.3525(10) ?
C12 H12 0.9500 ?
C13 H13 0.9500 ?
C15 H15A 0.9800 ?
C15 H15B 0.9800 ?
C15 H15C 0.9800 ?
C16 H00A 0.9800 ?
C16 H00B 0.9800 ?
C16 H00C 0.9800 ?
C17 C22 1.3994(10) ?
C17 C18 1.4081(10) ?
C18 C19 1.3893(10) ?
C18 H18 0.9500 ?
C19 C20 1.3913(11) ?
C19 H19 0.9500 ?
C20 C21 1.3868(11) ?
C20 H20 0.9500 ?
C21 C22 1.3855(10) ?
C22 H22 0.9500 ?
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
_geom_hbond_publ_flag
C1 H1 O3 3_656 0.95 2.55 3.3223(11) 139 y
C16 H00B N5 3_766 0.98 2.50 3.4757(11) 172 y
C16 H00C N3 1_556 0.98 2.61 3.5557(11) 163 y
C8 H8 N9 3_756 0.95 2.44 3.3882(10) 178 y
C13 H13 N3 3_766 0.95 2.60 3.5441(10) 174 y
C15 H15B O4 1_655 0.98 2.48 3.3692(11) 151 y
C4 H4C Cg3 4_554 0.98 2.96 3.8391(9) 150 y
C15 H15A Cg2 1_556 0.98 2.80 3.5398(9) 132 y
