#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/77/2227799.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227799
loop_
_publ_author_name
'Li, Chi-Huan'
'Su, Jing-Kai'
'Li, Chen-Yu'
'Ko, Bao-Tsan'
_publ_section_title
;
 (E)-2-(2H-Benzotriazol-2-yl)-4-methyl-6-(phenyliminomethyl)phenol
;
_journal_coeditor_code           LH5146
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2825
_journal_paper_doi               10.1107/S1600536810040468
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H16 N4 O'
_chemical_formula_moiety         'C20 H16 N4 O'
_chemical_formula_sum            'C20 H16 N4 O'
_chemical_formula_weight         328.37
_chemical_name_systematic
;
(E)-2-(2H-Benzotriazol-2-yl)-4-methyl-6-(phenyliminomethyl)phenol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.8420(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.7279(5)
_cell_length_b                   12.3002(4)
_cell_length_c                   8.4903(3)
_cell_measurement_reflns_used    5818
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.68
_cell_volume                     1587.70(9)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15472
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_T_min  0.9588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0542
_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)+(0.0585P)²+1.1196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1431
_reflns_number_gt                2874
_reflns_number_total             3924
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5146.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227799
_cod_database_fobs_code          2227799
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.33970(8) 0.05791(10) 0.32102(16) 0.0282(3) Uani d . 1 . .
H H0A 0.3839 0.0749 0.3960 0.042 Uiso calc R 1 . .
N N1 0.44430(10) 0.18656(12) 0.52339(19) 0.0261(3) Uani d . 1 . .
N N2 0.39775(10) 0.27027(12) 0.44505(18) 0.0237(3) Uani d . 1 . .
N N3 0.42414(10) 0.36903(12) 0.50100(19) 0.0260(3) Uani d . 1 . .
N N4 0.12957(11) 0.00970(13) -0.0541(2) 0.0300(4) Uani d . 1 . .
C C1 0.29886(11) 0.14915(14) 0.2511(2) 0.0236(4) Uani d . 1 . .
C C2 0.32445(11) 0.25450(14) 0.3077(2) 0.0236(4) Uani d . 1 . .
C C3 0.27847(12) 0.34491(14) 0.2315(2) 0.0255(4) Uani d . 1 . .
H H3B 0.2969 0.4155 0.2713 0.031 Uiso calc R 1 . .
C C4 0.20630(12) 0.33396(14) 0.0987(2) 0.0262(4) Uani d . 1 . .
C C5 0.18144(12) 0.22937(15) 0.0425(2) 0.0263(4) Uani d . 1 . .
H H5A 0.1322 0.2204 -0.0486 0.032 Uiso calc R 1 . .
C C6 0.22639(12) 0.13762(14) 0.1156(2) 0.0250(4) Uani d . 1 . .
C C7 0.50721(11) 0.23467(15) 0.6408(2) 0.0246(4) Uani d . 1 . .
C C8 0.57746(12) 0.18910(16) 0.7620(2) 0.0297(4) Uani d . 1 . .
H H8A 0.5866 0.1128 0.7720 0.036 Uiso calc R 1 . .
C C9 0.63115(12) 0.26085(17) 0.8633(2) 0.0313(4) Uani d . 1 . .
H H9A 0.6789 0.2335 0.9463 0.038 Uiso calc R 1 . .
C C10 0.61819(12) 0.37458(16) 0.8491(2) 0.0317(4) Uani d . 1 . .
H H10A 0.6575 0.4209 0.9230 0.038 Uiso calc R 1 . .
C C11 0.55176(13) 0.41972(16) 0.7340(2) 0.0300(4) Uani d . 1 . .
H H11A 0.5440 0.4963 0.7256 0.036 Uiso calc R 1 . .
C C12 0.49490(12) 0.34845(15) 0.6274(2) 0.0250(4) Uani d . 1 . .
C C13 0.15659(13) 0.43184(15) 0.0165(2) 0.0324(4) Uani d . 1 . .
H H13A 0.1404 0.4780 0.0983 0.049 Uiso calc R 1 . .
H H13B 0.1033 0.4080 -0.0636 0.049 Uiso calc R 1 . .
H H13C 0.1938 0.4732 -0.0385 0.049 Uiso calc R 1 . .
C C14 0.20102(12) 0.02858(15) 0.0498(2) 0.0266(4) Uani d . 1 . .
H H14A 0.2401 -0.0302 0.0872 0.032 Uiso calc R 1 . .
C C15 0.11424(13) -0.09878(15) -0.1139(2) 0.0289(4) Uani d . 1 . .
C C16 0.17777(13) -0.15712(16) -0.1667(2) 0.0326(4) Uani d . 1 . .
H H16A 0.2324 -0.1241 -0.1664 0.039 Uiso calc R 1 . .
C C17 0.16105(14) -0.26315(17) -0.2193(3) 0.0372(5) Uani d . 1 . .
H H17A 0.2043 -0.3025 -0.2561 0.045 Uiso calc R 1 . .
C C18 0.08242(14) -0.31249(17) -0.2191(3) 0.0372(5) Uani d . 1 . .
H H18A 0.0722 -0.3862 -0.2520 0.045 Uiso calc R 1 . .
C C19 0.01889(14) -0.25433(17) -0.1710(3) 0.0362(5) Uani d . 1 . .
H H19A -0.0356 -0.2880 -0.1720 0.043 Uiso calc R 1 . .
C C20 0.03324(13) -0.14724(17) -0.1210(2) 0.0339(4) Uani d . 1 . .
H H20A -0.0119 -0.1070 -0.0917 0.041 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
C1 O H0A . . 109.5 ?
N2 N1 C7 . . 103.56(15) ?
N3 N2 N1 . . 116.36(14) ?
N3 N2 C2 . . 121.88(14) ?
N1 N2 C2 . . 121.76(14) ?
N2 N3 C12 . . 103.27(14) ?
C14 N4 C15 . . 117.45(16) ?
O C1 C6 . . 118.06(16) ?
O C1 C2 . . 123.58(16) ?
C6 C1 C2 . . 118.35(16) ?
C3 C2 C1 . . 120.56(17) ?
C3 C2 N2 . . 119.07(16) ?
C1 C2 N2 . . 120.37(15) ?
C4 C3 C2 . . 121.34(17) ?
C4 C3 H3B . . 119.3 ?
C2 C3 H3B . . 119.3 ?
C3 C4 C5 . . 117.88(16) ?
C3 C4 C13 . . 121.25(17) ?
C5 C4 C13 . . 120.86(17) ?
C6 C5 C4 . . 122.06(17) ?
C6 C5 H5A . . 119.0 ?
C4 C5 H5A . . 119.0 ?
C5 C6 C1 . . 119.80(16) ?
C5 C6 C14 . . 120.93(17) ?
C1 C6 C14 . . 119.24(16) ?
N1 C7 C12 . . 108.40(16) ?
N1 C7 C8 . . 130.60(17) ?
C12 C7 C8 . . 121.00(17) ?
C9 C8 C7 . . 116.32(18) ?
C9 C8 H8A . . 121.8 ?
C7 C8 H8A . . 121.8 ?
C8 C9 C10 . . 122.26(19) ?
C8 C9 H9A . . 118.9 ?
C10 C9 H9A . . 118.9 ?
C11 C10 C9 . . 122.34(19) ?
C11 C10 H10A . . 118.8 ?
C9 C10 H10A . . 118.8 ?
C10 C11 C12 . . 117.10(18) ?
C10 C11 H11A . . 121.4 ?
C12 C11 H11A . . 121.4 ?
N3 C12 C11 . . 130.60(17) ?
N3 C12 C7 . . 108.41(16) ?
C11 C12 C7 . . 120.98(18) ?
C4 C13 H13A . . 109.5 ?
C4 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C4 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N4 C14 C6 . . 122.78(17) ?
N4 C14 H14A . . 118.6 ?
C6 C14 H14A . . 118.6 ?
C20 C15 C16 . . 119.25(18) ?
C20 C15 N4 . . 118.99(17) ?
C16 C15 N4 . . 121.76(17) ?
C17 C16 C15 . . 119.81(19) ?
C17 C16 H16A . . 120.1 ?
C15 C16 H16A . . 120.1 ?
C18 C17 C16 . . 120.77(19) ?
C18 C17 H17A . . 119.6 ?
C16 C17 H17A . . 119.6 ?
C19 C18 C17 . . 119.52(19) ?
C19 C18 H18A . . 120.2 ?
C17 C18 H18A . . 120.2 ?
C18 C19 C20 . . 120.85(19) ?
C18 C19 H19A . . 119.6 ?
C20 C19 H19A . . 119.6 ?
C19 C20 C15 . . 119.70(19) ?
C19 C20 H20A . . 120.1 ?
C15 C20 H20A . . 120.1 ?
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
O C1 . 1.352(2) ?
O H0A . 0.8400 ?
N1 N2 . 1.338(2) ?
N1 C7 . 1.348(2) ?
N2 N3 . 1.331(2) ?
N2 C2 . 1.427(2) ?
N3 C12 . 1.358(2) ?
N4 C14 . 1.260(2) ?
N4 C15 . 1.426(2) ?
C1 C6 . 1.404(3) ?
C1 C2 . 1.405(2) ?
C2 C3 . 1.392(2) ?
C3 C4 . 1.386(3) ?
C3 H3B . 0.9500 ?
C4 C5 . 1.393(2) ?
C4 C13 . 1.506(2) ?
C5 C6 . 1.391(2) ?
C5 H5A . 0.9500 ?
C6 C14 . 1.468(2) ?
C7 C12 . 1.413(3) ?
C7 C8 . 1.418(3) ?
C8 C9 . 1.364(3) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.414(3) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.354(3) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.404(3) ?
C11 H11A . 0.9500 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 H14A . 0.9500 ?
C15 C20 . 1.394(3) ?
C15 C16 . 1.394(3) ?
C16 C17 . 1.382(3) ?
C16 H16A . 0.9500 ?
C17 C18 . 1.378(3) ?
C17 H17A . 0.9500 ?
C18 C19 . 1.373(3) ?
C18 H18A . 0.9500 ?
C19 C20 . 1.385(3) ?
C19 H19A . 0.9500 ?
C20 H20A . 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
O H0A N1 . 0.84 1.852 2.591(2) 145.9
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
C7 N1 N2 N3 . . . . -0.34(18) ?
C7 N1 N2 C2 . . . . 178.92(14) ?
N1 N2 N3 C12 . . . . 0.31(18) ?
C2 N2 N3 C12 . . . . -178.95(14) ?
O C1 C2 C3 . . . . -178.92(15) ?
C6 C1 C2 C3 . . . . 0.4(2) ?
O C1 C2 N2 . . . . 0.7(2) ?
C6 C1 C2 N2 . . . . -179.96(15) ?
N3 N2 C2 C3 . . . . -0.9(2) ?
N1 N2 C2 C3 . . . . 179.87(15) ?
N3 N2 C2 C1 . . . . 179.46(15) ?
N1 N2 C2 C1 . . . . 0.2(2) ?
C1 C2 C3 C4 . . . . 0.3(3) ?
N2 C2 C3 C4 . . . . -179.37(15) ?
C2 C3 C4 C5 . . . . -0.6(3) ?
C2 C3 C4 C13 . . . . 179.92(16) ?
C3 C4 C5 C6 . . . . 0.2(3) ?
C13 C4 C5 C6 . . . . 179.72(16) ?
C4 C5 C6 C1 . . . . 0.5(3) ?
C4 C5 C6 C14 . . . . -177.48(16) ?
O C1 C6 C5 . . . . 178.60(15) ?
C2 C1 C6 C5 . . . . -0.8(2) ?
O C1 C6 C14 . . . . -3.4(2) ?
C2 C1 C6 C14 . . . . 177.22(15) ?
N2 N1 C7 C12 . . . . 0.21(17) ?
N2 N1 C7 C8 . . . . -178.95(17) ?
N1 C7 C8 C9 . . . . 179.37(18) ?
C12 C7 C8 C9 . . . . 0.3(2) ?
C7 C8 C9 C10 . . . . -0.2(3) ?
C8 C9 C10 C11 . . . . -0.1(3) ?
C9 C10 C11 C12 . . . . 0.2(3) ?
N2 N3 C12 C11 . . . . 179.15(18) ?
N2 N3 C12 C7 . . . . -0.15(18) ?
C10 C11 C12 N3 . . . . -179.33(17) ?
C10 C11 C12 C7 . . . . -0.1(3) ?
N1 C7 C12 N3 . . . . -0.04(19) ?
C8 C7 C12 N3 . . . . 179.22(15) ?
N1 C7 C12 C11 . . . . -179.42(15) ?
C8 C7 C12 C11 . . . . -0.2(3) ?
C15 N4 C14 C6 . . . . 177.26(16) ?
C5 C6 C14 N4 . . . . -13.4(3) ?
C1 C6 C14 N4 . . . . 168.64(17) ?
C14 N4 C15 C20 . . . . 132.8(2) ?
C14 N4 C15 C16 . . . . -47.7(3) ?
C20 C15 C16 C17 . . . . -2.4(3) ?
N4 C15 C16 C17 . . . . 178.13(18) ?
C15 C16 C17 C18 . . . . -0.6(3) ?
C16 C17 C18 C19 . . . . 2.2(3) ?
C17 C18 C19 C20 . . . . -0.7(3) ?
C18 C19 C20 C15 . . . . -2.2(3) ?
C16 C15 C20 C19 . . . . 3.8(3) ?
N4 C15 C20 C19 . . . . -176.73(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656283
