#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/86/2228686.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_2228686
loop_
_publ_author_name
'He, Guo-Fang'
'Shi, Zhi-Qiang'
_publ_section_title
;
 2-(1H-1,2,3-Benzotriazol-1-yl)-N'-(2-chlorobenzylidene)acetohydrazide
;
_journal_coeditor_code           CV5009
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o48
_journal_paper_doi               10.1107/S1600536810050440
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H12 Cl N5 O'
_chemical_formula_moiety         'C15 H12 Cl N5 O'
_chemical_formula_sum            'C15 H12 Cl N5 O'
_chemical_formula_weight         313.75
_chemical_name_systematic
;
2-(1H-1,2,3-Benzotriazol-1-yl)-N'-(2-
chlorobenzylidene)acetohydrazide
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.224(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.6777(16)
_cell_length_b                   11.726(4)
_cell_length_c                   13.328(5)
_cell_measurement_reflns_used    676
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      18.91
_cell_measurement_theta_min      2.32
_cell_volume                     729.1(4)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3851
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.173
_refine_ls_abs_structure_details 'Flack (1983), 544 Flack pairs'
_refine_ls_abs_structure_Flack   0.55(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0433
_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)+(0.0267P)²+0.1806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0894
_reflns_number_gt                1370
_reflns_number_total             1902
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5009.cif
_cod_data_source_block           I
_cod_original_cell_volume        729.0(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2228686
_cod_database_fobs_code          2228686
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
Cl Cl1 1.5224(3) 0.95422(11) 0.46424(9) 0.0660(4) Uani d . 1 . .
O O1 0.7318(6) 0.5815(3) 0.17718(18) 0.0473(8) Uani d . 1 . .
N N1 0.9309(7) 0.4707(3) 0.0172(2) 0.0377(8) Uani d . 1 . .
N N2 0.9247(9) 0.3561(3) 0.0325(3) 0.0523(10) Uani d . 1 . .
N N3 0.7297(9) 0.3113(3) -0.0307(3) 0.0561(11) Uani d . 1 . .
N N4 1.1772(7) 0.6360(3) 0.2368(2) 0.0413(9) Uani d . 1 . .
H H4 1.3555 0.6412 0.2257 0.050 Uiso calc R 1 . .
N N5 1.0786(8) 0.6779(3) 0.3252(2) 0.0391(9) Uani d . 1 . .
C C1 0.7313(9) 0.5002(4) -0.0583(3) 0.0361(10) Uani d . 1 . .
C C2 0.6509(10) 0.6045(4) -0.1011(3) 0.0466(11) Uani d . 1 . .
H H2 0.7386 0.6726 -0.0805 0.056 Uiso calc R 1 . .
C C3 0.4329(11) 0.6000(5) -0.1759(3) 0.0619(14) Uani d . 1 . .
H H3 0.3692 0.6677 -0.2063 0.074 Uiso calc R 1 . .
C C4 0.3028(11) 0.4976(6) -0.2083(3) 0.0632(15) Uani d . 1 . .
H H4A 0.1586 0.4996 -0.2602 0.076 Uiso calc R 1 . .
C C5 0.3809(10) 0.3947(5) -0.1661(3) 0.0585(14) Uani d . 1 . .
H H5 0.2931 0.3269 -0.1874 0.070 Uiso calc R 1 . .
C C6 0.6035(10) 0.3978(4) -0.0881(3) 0.0437(11) Uani d . 1 . .
C C7 1.1297(9) 0.5398(4) 0.0782(3) 0.0427(11) Uani d . 1 . .
H H7A 1.1955 0.6024 0.0383 0.051 Uiso calc R 1 . .
H H7B 1.2950 0.4943 0.1011 0.051 Uiso calc R 1 . .
C C8 0.9886(9) 0.5868(4) 0.1684(3) 0.0354(9) Uani d . 1 . .
C C9 1.2636(10) 0.7317(3) 0.3822(3) 0.0421(11) Uani d . 1 . .
H H9 1.4451 0.7469 0.3612 0.050 Uiso calc R 1 . .
C C10 1.1839(9) 0.7691(4) 0.4815(3) 0.0406(10) Uani d . 1 . .
C C11 1.2939(9) 0.8682(4) 0.5275(3) 0.0446(11) Uani d . 1 . .
C C12 1.2219(10) 0.8998(4) 0.6219(3) 0.0564(13) Uani d . 1 . .
H H12 1.2975 0.9660 0.6516 0.068 Uiso calc R 1 . .
C C13 1.0391(12) 0.8333(5) 0.6715(3) 0.0608(15) Uani d . 1 . .
H H13 0.9924 0.8544 0.7355 0.073 Uiso calc R 1 . .
C C14 0.9219(11) 0.7351(4) 0.6283(3) 0.0569(14) Uani d . 1 . .
H H14 0.7953 0.6908 0.6623 0.068 Uiso calc R 1 . .
C C15 0.9967(10) 0.7035(4) 0.5332(3) 0.0481(12) Uani d . 1 . .
H H15 0.9198 0.6374 0.5038 0.058 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'
Cl Cl 0.1484 0.1585 '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
N2 N1 C1 . . 109.9(4) ?
N2 N1 C7 . . 119.5(4) ?
C1 N1 C7 . . 130.6(3) ?
N3 N2 N1 . . 108.8(4) ?
N2 N3 C6 . . 108.2(3) ?
C8 N4 N5 . . 118.9(3) ?
C8 N4 H4 . . 120.5 ?
N5 N4 H4 . . 120.5 ?
C9 N5 N4 . . 115.3(3) ?
N1 C1 C6 . . 104.4(3) ?
N1 C1 C2 . . 132.5(4) ?
C6 C1 C2 . . 123.1(4) ?
C3 C2 C1 . . 115.4(5) ?
C3 C2 H2 . . 122.3 ?
C1 C2 H2 . . 122.3 ?
C2 C3 C4 . . 122.6(5) ?
C2 C3 H3 . . 118.7 ?
C4 C3 H3 . . 118.7 ?
C5 C4 C3 . . 122.2(5) ?
C5 C4 H4A . . 118.9 ?
C3 C4 H4A . . 118.9 ?
C4 C5 C6 . . 116.0(5) ?
C4 C5 H5 . . 122.0 ?
C6 C5 H5 . . 122.0 ?
N3 C6 C1 . . 108.7(4) ?
N3 C6 C5 . . 130.6(4) ?
C1 C6 C5 . . 120.7(4) ?
N1 C7 C8 . . 110.6(3) ?
N1 C7 H7A . . 109.5 ?
C8 C7 H7A . . 109.5 ?
N1 C7 H7B . . 109.5 ?
C8 C7 H7B . . 109.5 ?
H7A C7 H7B . . 108.1 ?
O1 C8 N4 . . 123.9(4) ?
O1 C8 C7 . . 123.2(4) ?
N4 C8 C7 . . 112.9(4) ?
N5 C9 C10 . . 118.5(4) ?
N5 C9 H9 . . 120.7 ?
C10 C9 H9 . . 120.7 ?
C15 C10 C11 . . 118.0(3) ?
C15 C10 C9 . . 119.6(4) ?
C11 C10 C9 . . 122.4(4) ?
C12 C11 C10 . . 121.3(4) ?
C12 C11 Cl1 . . 119.3(4) ?
C10 C11 Cl1 . . 119.5(3) ?
C13 C12 C11 . . 119.6(4) ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C12 C13 C14 . . 121.2(4) ?
C12 C13 H13 . . 119.4 ?
C14 C13 H13 . . 119.4 ?
C13 C14 C15 . . 118.8(5) ?
C13 C14 H14 . . 120.6 ?
C15 C14 H14 . . 120.6 ?
C10 C15 C14 . . 121.1(4) ?
C10 C15 H15 . . 119.4 ?
C14 C15 H15 . . 119.4 ?
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
Cl1 C11 . 1.733(4) ?
O1 C8 . 1.217(4) ?
N1 N2 . 1.359(5) ?
N1 C1 . 1.366(5) ?
N1 C7 . 1.440(5) ?
N2 N3 . 1.306(5) ?
N3 C6 . 1.377(5) ?
N4 C8 . 1.350(5) ?
N4 N5 . 1.387(4) ?
N4 H4 . 0.8600 ?
N5 C9 . 1.275(5) ?
C1 C6 . 1.387(5) ?
C1 C2 . 1.389(6) ?
C2 C3 . 1.374(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.399(7) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.370(7) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.416(6) ?
C5 H5 . 0.9300 ?
C7 C8 . 1.517(5) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C9 C10 . 1.468(5) ?
C9 H9 . 0.9300 ?
C10 C15 . 1.386(6) ?
C10 C11 . 1.394(5) ?
C11 C12 . 1.377(5) ?
C12 C13 . 1.364(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.383(7) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.390(6) ?
C14 H14 . 0.9300 ?
C15 H15 . 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
N4 H4 O1 1_655 0.86 2.04 2.841(4) 154.0
C7 H7A N3 2_755 0.97 2.48 3.320(6) 145.3
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
C1 N1 N2 N3 . . . . 0.4(4) ?
C7 N1 N2 N3 . . . . 179.9(3) ?
N1 N2 N3 C6 . . . . -0.5(5) ?
C8 N4 N5 C9 . . . . -174.3(4) ?
N2 N1 C1 C6 . . . . -0.1(4) ?
C7 N1 C1 C6 . . . . -179.6(4) ?
N2 N1 C1 C2 . . . . 179.1(4) ?
C7 N1 C1 C2 . . . . -0.4(7) ?
N1 C1 C2 C3 . . . . -178.9(4) ?
C6 C1 C2 C3 . . . . 0.2(6) ?
C1 C2 C3 C4 . . . . -1.0(6) ?
C2 C3 C4 C5 . . . . 1.2(8) ?
C3 C4 C5 C6 . . . . -0.5(7) ?
N2 N3 C6 C1 . . . . 0.5(5) ?
N2 N3 C6 C5 . . . . -179.5(4) ?
N1 C1 C6 N3 . . . . -0.2(4) ?
C2 C1 C6 N3 . . . . -179.5(4) ?
N1 C1 C6 C5 . . . . 179.7(3) ?
C2 C1 C6 C5 . . . . 0.4(6) ?
C4 C5 C6 N3 . . . . 179.7(5) ?
C4 C5 C6 C1 . . . . -0.2(6) ?
N2 N1 C7 C8 . . . . -93.6(4) ?
C1 N1 C7 C8 . . . . 85.8(5) ?
N5 N4 C8 O1 . . . . 3.6(6) ?
N5 N4 C8 C7 . . . . -177.1(3) ?
N1 C7 C8 O1 . . . . -11.3(6) ?
N1 C7 C8 N4 . . . . 169.5(3) ?
N4 N5 C9 C10 . . . . -174.2(3) ?
N5 C9 C10 C15 . . . . 33.0(6) ?
N5 C9 C10 C11 . . . . -148.1(4) ?
C15 C10 C11 C12 . . . . 0.7(6) ?
C9 C10 C11 C12 . . . . -178.2(4) ?
C15 C10 C11 Cl1 . . . . -178.6(3) ?
C9 C10 C11 Cl1 . . . . 2.6(6) ?
C10 C11 C12 C13 . . . . -0.2(7) ?
Cl1 C11 C12 C13 . . . . 179.1(4) ?
C11 C12 C13 C14 . . . . -0.7(7) ?
C12 C13 C14 C15 . . . . 0.9(7) ?
C11 C10 C15 C14 . . . . -0.4(6) ?
C9 C10 C15 C14 . . . . 178.5(4) ?
C13 C14 C15 C10 . . . . -0.4(7) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7889853
