#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/12/2221256.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_2221256
loop_
_publ_author_name
'Ravindran Durai Nayagam, B.'
'Jebas, Samuel Robinson'
'Edward Rajkumar, J. P'
'Schollmeyer, Dieter'
_publ_section_title
;
 1-(2,3,5,6-Tetramethylbenzyloxy)-1H-benzotriazole
;
_journal_coeditor_code           AT2749
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o917
_journal_paper_doi               10.1107/S1600536809010794
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H19 N3 O'
_chemical_formula_moiety         'C17 H19 N3 O'
_chemical_formula_sum            'C17 H19 N3 O'
_chemical_formula_weight         281.35
_chemical_name_systematic
;
1-(2,3,5,6-Tetramethylbenzyloxy)-1H-benzotriazole
;
_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                 105.977(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9737(8)
_cell_length_b                   26.3838(18)
_cell_length_c                   11.490(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      70
_cell_measurement_theta_min      65
_cell_volume                     1449.5(4)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'CORINC (Draeger & Gattow, 1971)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2861
_diffrn_reflns_theta_full        69.92
_diffrn_reflns_theta_max         69.92
_diffrn_reflns_theta_min         3.35
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  0.7588
_exptl_absorpt_correction_T_min  0.7312
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(CORINC; Draeger & Gattow, 1971)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.229
_refine_ls_extinction_coef       0.0042(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max_lt       0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0664P)²+0.687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1330
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                2578
_reflns_number_total             2729
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2749.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221256
_cod_database_fobs_code          2221256
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
N N1 0.4809(3) 0.32620(5) 0.62810(11) 0.0311(3) Uani d . 1 . .
N N2 0.3357(3) 0.28455(5) 0.63903(13) 0.0379(4) Uani d . 1 . .
N N3 0.4680(3) 0.26168(5) 0.73894(13) 0.0395(4) Uani d . 1 . .
C C4 0.7028(3) 0.28997(6) 0.79380(14) 0.0321(4) Uani d . 1 . .
C C5 0.9114(4) 0.28229(6) 0.90326(15) 0.0374(4) Uani d . 1 . .
H H5 0.9065 0.2539 0.9536 0.045 Uiso calc R 1 . .
C C6 1.1208(4) 0.31732(7) 0.93407(15) 0.0411(4) Uani d . 1 . .
H H6 1.2652 0.3131 1.0072 0.049 Uiso calc R 1 . .
C C7 1.1281(4) 0.35962(7) 0.86002(16) 0.0412(4) Uani d . 1 . .
H H7 1.2779 0.3831 0.8849 0.049 Uiso calc R 1 . .
C C8 0.9264(3) 0.36815(6) 0.75324(15) 0.0348(4) Uani d . 1 . .
H H8 0.9317 0.3967 0.7036 0.042 Uiso calc R 1 . .
C C9 0.7132(3) 0.33208(6) 0.72239(13) 0.0292(4) Uani d . 1 . .
O O10 0.3754(2) 0.35998(4) 0.53578(9) 0.0327(3) Uani d . 1 . .
C C11 0.4691(4) 0.34745(6) 0.42841(14) 0.0328(4) Uani d . 1 . .
H H11A 0.3904 0.3145 0.3939 0.039 Uiso calc R 1 . .
H H11B 0.6757 0.3455 0.4497 0.039 Uiso calc R 1 . .
C C12 0.3636(3) 0.38958(6) 0.33973(13) 0.0286(4) Uani d . 1 . .
C C13 0.5113(3) 0.43544(6) 0.35296(13) 0.0296(4) Uani d . 1 . .
C C14 0.4080(3) 0.47548(6) 0.27302(14) 0.0316(4) Uani d . 1 . .
C C15 0.1584(3) 0.46843(6) 0.18303(14) 0.0335(4) Uani d . 1 . .
H H15 0.0869 0.4957 0.1294 0.040 Uiso calc R 1 . .
C C16 0.0095(3) 0.42330(7) 0.16838(13) 0.0318(4) Uani d . 1 . .
C C17 0.1116(3) 0.38296(6) 0.24756(13) 0.0299(4) Uani d . 1 . .
C C18 0.7813(3) 0.44365(7) 0.45103(15) 0.0389(4) Uani d . 1 . .
H H18A 0.8466 0.4113 0.4906 0.058 Uiso calc R 1 . .
H H18B 0.7492 0.4676 0.5110 0.058 Uiso calc R 1 . .
H H18C 0.9231 0.4574 0.4151 0.058 Uiso calc R 1 . .
C C19 0.5633(4) 0.52490(7) 0.28165(18) 0.0424(4) Uani d . 1 . .
H H19A 0.7451 0.5190 0.2664 0.064 Uiso calc R 1 . .
H H19B 0.5917 0.5392 0.3628 0.064 Uiso calc R 1 . .
H H19C 0.4541 0.5487 0.2214 0.064 Uiso calc R 1 . .
C C20 -0.2599(4) 0.41887(8) 0.06843(15) 0.0416(4) Uani d . 1 . .
H H20A -0.3033 0.4515 0.0268 0.062 Uiso calc R 1 . .
H H20B -0.4120 0.4093 0.1031 0.062 Uiso calc R 1 . .
H H20C -0.2393 0.3929 0.0106 0.062 Uiso calc R 1 . .
C C21 -0.0499(4) 0.33394(7) 0.23361(17) 0.0399(4) Uani d . 1 . .
H H21A -0.0717 0.3235 0.3124 0.060 Uiso calc R 1 . .
H H21B 0.0518 0.3076 0.2029 0.060 Uiso calc R 1 . .
H H21C -0.2348 0.3388 0.1765 0.060 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 C9 . . 112.41(13) ?
N2 N1 O10 . . 120.21(12) ?
C9 N1 O10 . . 127.02(13) ?
N3 N2 N1 . . 107.93(13) ?
N2 N3 C4 . . 108.04(14) ?
N3 C4 C9 . . 109.04(14) ?
N3 C4 C5 . . 130.67(16) ?
C9 C4 C5 . . 120.29(15) ?
C6 C5 C4 . . 117.17(16) ?
C6 C5 H5 . . 121.4 ?
C4 C5 H5 . . 121.4 ?
C5 C6 C7 . . 121.62(16) ?
C5 C6 H6 . . 119.2 ?
C7 C6 H6 . . 119.2 ?
C8 C7 C6 . . 122.35(16) ?
C8 C7 H7 . . 118.8 ?
C6 C7 H7 . . 118.8 ?
C7 C8 C9 . . 115.62(15) ?
C7 C8 H8 . . 122.2 ?
C9 C8 H8 . . 122.2 ?
N1 C9 C4 . . 102.58(14) ?
N1 C9 C8 . . 134.47(15) ?
C4 C9 C8 . . 122.95(15) ?
N1 O10 C11 . . 111.09(11) ?
O10 C11 C12 . . 105.69(12) ?
O10 C11 H11A . . 110.6 ?
C12 C11 H11A . . 110.6 ?
O10 C11 H11B . . 110.6 ?
C12 C11 H11B . . 110.6 ?
H11A C11 H11B . . 108.7 ?
C13 C12 C17 . . 121.24(14) ?
C13 C12 C11 . . 119.37(14) ?
C17 C12 C11 . . 119.33(14) ?
C14 C13 C12 . . 119.53(14) ?
C14 C13 C18 . . 118.07(15) ?
C12 C13 C18 . . 122.39(14) ?
C15 C14 C13 . . 118.49(15) ?
C15 C14 C19 . . 120.09(15) ?
C13 C14 C19 . . 121.41(15) ?
C16 C15 C14 . . 122.80(15) ?
C16 C15 H15 . . 118.6 ?
C14 C15 H15 . . 118.6 ?
C15 C16 C17 . . 119.15(14) ?
C15 C16 C20 . . 119.39(15) ?
C17 C16 C20 . . 121.45(16) ?
C16 C17 C12 . . 118.77(15) ?
C16 C17 C21 . . 119.69(14) ?
C12 C17 C21 . . 121.53(14) ?
C13 C18 H18A . . 109.5 ?
C13 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C13 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C14 C19 H19A . . 109.5 ?
C14 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C14 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C16 C20 H20A . . 109.5 ?
C16 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C16 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C17 C21 H21A . . 109.5 ?
C17 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C17 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
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
N1 N2 . 1.3398(19) ?
N1 C9 . 1.358(2) ?
N1 O10 . 1.3741(16) ?
N2 N3 . 1.304(2) ?
N3 C4 . 1.383(2) ?
C4 C9 . 1.390(2) ?
C4 C5 . 1.407(2) ?
C5 C6 . 1.364(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.410(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.373(2) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.396(2) ?
C8 H8 . 0.9500 ?
O10 C11 . 1.4714(19) ?
C11 C12 . 1.501(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.402(2) ?
C12 C17 . 1.412(2) ?
C13 C14 . 1.401(2) ?
C13 C18 . 1.512(2) ?
C14 C15 . 1.392(2) ?
C14 C19 . 1.505(2) ?
C15 C16 . 1.388(2) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.401(2) ?
C16 C20 . 1.510(2) ?
C17 C21 . 1.508(2) ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
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
C18 H18C Cg3 1_655 0.98 2.85 3.6701(18) 141
C20 H20B Cg3 1_455 0.98 2.80 3.682(2) 150
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
C9 N1 N2 N3 . . . . -0.72(19) ?
O10 N1 N2 N3 . . . . -174.26(13) ?
N1 N2 N3 C4 . . . . 0.67(18) ?
N2 N3 C4 C9 . . . . -0.41(19) ?
N2 N3 C4 C5 . . . . 179.01(17) ?
N3 C4 C5 C6 . . . . 179.99(17) ?
C9 C4 C5 C6 . . . . -0.6(2) ?
C4 C5 C6 C7 . . . . 0.3(3) ?
C5 C6 C7 C8 . . . . 0.1(3) ?
C6 C7 C8 C9 . . . . -0.1(3) ?
N2 N1 C9 C4 . . . . 0.44(17) ?
O10 N1 C9 C4 . . . . 173.45(14) ?
N2 N1 C9 C8 . . . . -179.69(17) ?
O10 N1 C9 C8 . . . . -6.7(3) ?
N3 C4 C9 N1 . . . . -0.01(17) ?
C5 C4 C9 N1 . . . . -179.51(15) ?
N3 C4 C9 C8 . . . . -179.90(15) ?
C5 C4 C9 C8 . . . . 0.6(2) ?
C7 C8 C9 N1 . . . . 179.94(17) ?
C7 C8 C9 C4 . . . . -0.2(2) ?
N2 N1 O10 C11 . . . . -91.18(17) ?
C9 N1 O10 C11 . . . . 96.30(17) ?
N1 O10 C11 C12 . . . . -174.71(12) ?
O10 C11 C12 C13 . . . . 80.40(17) ?
O10 C11 C12 C17 . . . . -97.09(16) ?
C17 C12 C13 C14 . . . . -0.3(2) ?
C11 C12 C13 C14 . . . . -177.69(14) ?
C17 C12 C13 C18 . . . . 179.83(14) ?
C11 C12 C13 C18 . . . . 2.4(2) ?
C12 C13 C14 C15 . . . . 0.6(2) ?
C18 C13 C14 C15 . . . . -179.49(14) ?
C12 C13 C14 C19 . . . . -178.35(14) ?
C18 C13 C14 C19 . . . . 1.6(2) ?
C13 C14 C15 C16 . . . . -0.7(2) ?
C19 C14 C15 C16 . . . . 178.23(15) ?
C14 C15 C16 C17 . . . . 0.5(2) ?
C14 C15 C16 C20 . . . . 179.92(15) ?
C15 C16 C17 C12 . . . . -0.1(2) ?
C20 C16 C17 C12 . . . . -179.53(14) ?
C15 C16 C17 C21 . . . . 179.26(14) ?
C20 C16 C17 C21 . . . . -0.2(2) ?
C13 C12 C17 C16 . . . . 0.0(2) ?
C11 C12 C17 C16 . . . . 177.45(13) ?
C13 C12 C17 C21 . . . . -179.36(14) ?
C11 C12 C17 C21 . . . . -1.9(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742037
