#------------------------------------------------------------------------------
#$Date: 2018-08-15 05:12:26 +0300 (Wed, 15 Aug 2018) $
#$Revision: 209709 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/25/2242583.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_2242583
loop_
_publ_author_name
'Zukerman-Schpector, Julio'
'Dias, Cássio da S.'
'Schwab, Ricardo S.'
'Jotani, Mukesh M.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 4-(4-Acetyl-5-methyl-1H-1,2,3-triazol-1-yl)benzonitrile: crystal
 structure and Hirshfeld surface analysis
;
_journal_coeditor_code           HB7764
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1195
_journal_page_last               1200
_journal_paper_doi               10.1107/S2056989018010885
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C12 H10 N4 O'
_chemical_formula_moiety         'C12 H10 N4 O'
_chemical_formula_sum            'C12 H10 N4 O'
_chemical_formula_weight         226.24
_chemical_name_systematic
;
4-(4-Acetyl-5-methyl-1H-1,2,3-triazol-1-yl)benzonitrile
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 107.4770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8533(5)
_cell_length_b                   6.8299(3)
_cell_length_c                   14.7329(6)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.29
_cell_measurement_theta_min      2.63
_cell_volume                     1137.67(8)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2014 (Burla et al., 2015)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30812
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.380
_diffrn_reflns_theta_min         1.943
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       irregular
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.202
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0573P)²+0.3916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1264
_reflns_number_gt                2083
_reflns_number_total             2333
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7764sup1.cif
_cod_data_source_block           I
_cod_database_code               2242583
_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   0.961
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.39515(11) 0.7197(2) 0.36712(11) 0.0785(5) Uani d 1
N N1 0.73587(10) 0.95924(17) 0.48424(8) 0.0357(3) Uani d 1
N N2 0.70535(11) 1.13354(19) 0.43684(10) 0.0476(3) Uani d 1
N N3 0.59641(11) 1.11608(19) 0.38456(10) 0.0462(3) Uani d 1
N N4 1.27442(13) 0.8725(3) 0.80947(11) 0.0623(4) Uani d 1
C C1 0.64418(11) 0.8326(2) 0.46207(10) 0.0364(3) Uani d 1
C C2 0.55549(12) 0.9350(2) 0.39775(10) 0.0364(3) Uani d 1
C C3 0.43345(13) 0.8728(2) 0.34833(11) 0.0451(4) Uani d 1
C C4 0.64687(15) 0.6346(3) 0.50374(14) 0.0614(5) Uani d 1
H H4A 0.7168 0.6210 0.5570 0.092 Uiso calc 1
H H4B 0.6473 0.5378 0.4566 0.092 Uiso calc 1
H H4C 0.5782 0.6168 0.5246 0.092 Uiso calc 1
C C5 0.35961(15) 1.0069(3) 0.27426(14) 0.0668(6) Uani d 1
H H5A 0.3902 1.0108 0.2209 0.100 Uiso calc 1
H H5B 0.3615 1.1361 0.3004 0.100 Uiso calc 1
H H5C 0.2795 0.9602 0.2538 0.100 Uiso calc 1
C C6 0.85161(11) 0.9389(2) 0.55064(9) 0.0354(3) Uani d 1
C C7 0.92321(13) 0.7849(2) 0.54291(11) 0.0454(4) Uani d 1
H H7 0.8976 0.6944 0.4938 0.054 Uiso calc 1
C C8 1.03376(14) 0.7662(2) 0.60904(11) 0.0482(4) Uani d 1
H H8 1.0827 0.6622 0.6050 0.058 Uiso calc 1
C C9 1.07120(12) 0.9032(2) 0.68124(10) 0.0403(3) Uani d 1
C C10 0.99970(13) 1.0600(3) 0.68695(11) 0.0494(4) Uani d 1
H H10 1.0261 1.1532 0.7347 0.059 Uiso calc 1
C C11 0.88901(13) 1.0776(2) 0.62138(11) 0.0472(4) Uani d 1
H H11 0.8401 1.1820 0.6249 0.057 Uiso calc 1
C C12 1.18561(13) 0.8846(3) 0.75178(11) 0.0470(4) Uani 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
C1 N1 N2 111.26(11)
C1 N1 C6 129.75(12)
N2 N1 C6 118.91(11)
N3 N2 N1 106.62(11)
N2 N3 C2 109.42(12)
N1 C1 C2 103.53(12)
N1 C1 C4 124.68(12)
C2 C1 C4 131.77(13)
N3 C2 C1 109.16(12)
N3 C2 C3 121.99(13)
C1 C2 C3 128.84(14)
O1 C3 C2 121.25(14)
O1 C3 C5 121.51(15)
C2 C3 C5 117.25(14)
C1 C4 H4A 109.5
C1 C4 H4B 109.5
H4A C4 H4B 109.5
C1 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C3 C5 H5A 109.5
C3 C5 H5B 109.5
H5A C5 H5B 109.5
C3 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C7 C6 C11 121.37(13)
C7 C6 N1 120.33(12)
C11 C6 N1 118.29(13)
C6 C7 C8 119.25(14)
C6 C7 H7 120.4
C8 C7 H7 120.4
C7 C8 C9 119.71(14)
C7 C8 H8 120.1
C9 C8 H8 120.1
C10 C9 C8 120.56(13)
C10 C9 C12 118.92(14)
C8 C9 C12 120.52(14)
C11 C10 C9 119.66(14)
C11 C10 H10 120.2
C9 C10 H10 120.2
C6 C11 C10 119.42(14)
C6 C11 H11 120.3
C10 C11 H11 120.3
N4 C12 C9 177.85(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.205(2)
N1 C1 1.3500(17)
N1 N2 1.3726(17)
N1 C6 1.4326(16)
N2 N3 1.2952(17)
N3 C2 1.3634(19)
N4 C12 1.140(2)
C1 C2 1.3762(19)
C1 C4 1.482(2)
C2 C3 1.4734(19)
C3 C5 1.491(2)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 C7 1.378(2)
C6 C11 1.379(2)
C7 C8 1.384(2)
C7 H7 0.9300
C8 C9 1.385(2)
C8 H8 0.9300
C9 C10 1.384(2)
C9 C12 1.4452(19)
C10 C11 1.381(2)
C10 H10 0.9300
C11 H11 0.9300
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 O1 Cg1 3_676 1.205(2) 3.6880(16) 3.7359(17) 82.92(10)
C12 N4 Cg1 4_565 1.140(2) 3.6794(19) 3.8468(19) 89.72(13)
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
C1 N1 N2 N3 -0.81(17)
C6 N1 N2 N3 -177.77(12)
N1 N2 N3 C2 0.54(17)
N2 N1 C1 C2 0.72(16)
C6 N1 C1 C2 177.26(13)
N2 N1 C1 C4 -177.72(16)
C6 N1 C1 C4 -1.2(2)
N2 N3 C2 C1 -0.10(18)
N2 N3 C2 C3 179.34(14)
N1 C1 C2 N3 -0.38(16)
C4 C1 C2 N3 177.90(17)
N1 C1 C2 C3 -179.78(14)
C4 C1 C2 C3 -1.5(3)
N3 C2 C3 O1 -173.09(17)
C1 C2 C3 O1 6.2(3)
N3 C2 C3 C5 6.9(2)
C1 C2 C3 C5 -173.75(16)
C1 N1 C6 C7 57.1(2)
N2 N1 C6 C7 -126.64(15)
C1 N1 C6 C11 -123.36(17)
N2 N1 C6 C11 52.95(19)
C11 C6 C7 C8 1.7(2)
N1 C6 C7 C8 -178.73(14)
C6 C7 C8 C9 -0.6(3)
C7 C8 C9 C10 -1.0(3)
C7 C8 C9 C12 179.08(15)
C8 C9 C10 C11 1.5(3)
C12 C9 C10 C11 -178.55(15)
C7 C6 C11 C10 -1.2(2)
N1 C6 C11 C10 179.25(14)
C9 C10 C11 C6 -0.4(3)

_cod_database_fobs_code 2242583
