#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/51/2225172.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_2225172
loop_
_publ_author_name
'Ravindran Durai Nayagam, B.'
'Jebas, Samuel Robinson'
'Shakina, J.'
'Murugesan., R.'
'Schollmeyer, Dieter'
_publ_section_title
;
 1-Mesitylmethyl-1Hbenzotriazole 3-oxide
;
_journal_coeditor_code           BT5182
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o637
_journal_paper_doi               10.1107/S1600536810004824
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H17 N3 O'
_chemical_formula_moiety         'C16 H17 N3 O'
_chemical_formula_sum            'C16 H17 N3 O'
_chemical_formula_weight         267.33
_chemical_name_common
'3-( 2-methylene mesitylene)1-oxo  benzotriazole'
_chemical_name_systematic
;
1-Mesitylmethyl-1Hbenzotriazole 3-oxide
;
_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                 103.133(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6269(19)
_cell_length_b                   7.3422(4)
_cell_length_c                   21.890(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      48
_cell_measurement_theta_min      35
_cell_volume                     1350.3(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  0.0913
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            2722
_diffrn_reflns_theta_full        69.93
_diffrn_reflns_theta_max         69.93
_diffrn_reflns_theta_min         4.15
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  0.9357
_exptl_absorpt_correction_T_min  0.7985
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(CORINC; Draeger & Gattow (1971)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2546
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0458
_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)+(0.0705P)²+0.4335P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1318
_reflns_number_gt                2243
_reflns_number_total             2545
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5182.cif
_cod_data_source_block           I
_cod_original_cell_volume        1350.2(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225172
_cod_database_fobs_code          2225172
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 0.70466(16) -0.01341(18) 0.11411(6) 0.0277(3) Uani d . 1 . .
C C2 0.71052(18) 0.0150(2) 0.05338(7) 0.0272(3) Uani d . 1 . .
C C3 0.7611(2) -0.0918(2) 0.00798(8) 0.0369(4) Uani d . 1 . .
H H3 0.7999 -0.2123 0.0167 0.044 Uiso calc R 1 . .
C C4 0.7513(2) -0.0124(3) -0.04902(8) 0.0411(4) Uani d . 1 . .
H H4 0.7846 -0.0801 -0.0808 0.049 Uiso calc R 1 . .
C C5 0.6933(2) 0.1673(3) -0.06290(8) 0.0364(4) Uani d . 1 . .
H H5 0.6900 0.2166 -0.1033 0.044 Uiso calc R 1 . .
C C6 0.64222(18) 0.2710(2) -0.01957(7) 0.0317(4) Uani d . 1 . .
H H6 0.6023 0.3909 -0.0286 0.038 Uiso calc R 1 . .
C C7 0.65231(17) 0.1899(2) 0.03868(7) 0.0262(3) Uani d . 1 . .
N N8 0.61389(15) 0.25395(18) 0.09300(6) 0.0285(3) Uani d . 1 . .
N N9 0.64505(16) 0.13267(18) 0.13845(6) 0.0294(3) Uani d . 1 . .
O O10 0.56088(16) 0.41370(17) 0.10077(6) 0.0416(3) Uani d . 1 . .
C C11 0.7402(2) -0.1818(2) 0.15108(7) 0.0308(4) Uani d . 1 . .
H H11A 0.8203 -0.2529 0.1352 0.037 Uiso calc R 1 . .
H H11B 0.6421 -0.2562 0.1450 0.037 Uiso calc R 1 . .
C C12 0.80200(18) -0.1471(2) 0.22014(7) 0.0258(3) Uani d . 1 . .
C C13 0.96499(17) -0.1154(2) 0.24416(7) 0.0278(3) Uani d . 1 . .
C C14 1.01987(18) -0.0911(2) 0.30840(8) 0.0307(4) Uani d . 1 . .
H H14 1.1305 -0.0728 0.3249 0.037 Uiso calc R 1 . .
C C15 0.9183(2) -0.0928(2) 0.34912(7) 0.0311(4) Uani d . 1 . .
C C16 0.75646(19) -0.1203(2) 0.32423(7) 0.0307(4) Uani d . 1 . .
H H16 0.6850 -0.1197 0.3515 0.037 Uiso calc R 1 . .
C C17 0.69733(18) -0.1485(2) 0.26051(7) 0.0272(3) Uani d . 1 . .
C C18 1.0814(2) -0.1051(2) 0.20228(9) 0.0396(4) Uani d . 1 . .
H H18A 1.0922 -0.2256 0.1844 0.059 Uiso calc R 1 . .
H H18B 1.1852 -0.0648 0.2269 0.059 Uiso calc R 1 . .
H H18C 1.0424 -0.0181 0.1683 0.059 Uiso calc R 1 . .
C C19 0.9812(2) -0.0637(3) 0.41845(8) 0.0460(5) Uani d . 1 . .
H H19A 0.9922 -0.1816 0.4400 0.069 Uiso calc R 1 . .
H H19B 0.9070 0.0132 0.4348 0.069 Uiso calc R 1 . .
H H19C 1.0853 -0.0039 0.4257 0.069 Uiso calc R 1 . .
C C20 0.52065(19) -0.1764(3) 0.23637(8) 0.0393(4) Uani d . 1 . .
H H20A 0.4771 -0.0771 0.2076 0.059 Uiso calc R 1 . .
H H20B 0.4684 -0.1772 0.2717 0.059 Uiso calc R 1 . .
H H20C 0.5017 -0.2929 0.2141 0.059 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
N9 N1 C2 . . 111.49(12) ?
N9 N1 C11 . . 120.06(12) ?
C2 N1 C11 . . 128.19(13) ?
N1 C2 C7 . . 106.08(13) ?
N1 C2 C3 . . 133.66(15) ?
C7 C2 C3 . . 120.26(14) ?
C4 C3 C2 . . 116.27(16) ?
C4 C3 H3 . . 121.9 ?
C2 C3 H3 . . 121.9 ?
C3 C4 C5 . . 122.64(16) ?
C3 C4 H4 . . 118.7 ?
C5 C4 H4 . . 118.7 ?
C6 C5 C4 . . 121.56(15) ?
C6 C5 H5 . . 119.2 ?
C4 C5 H5 . . 119.2 ?
C5 C6 C7 . . 115.80(16) ?
C5 C6 H6 . . 122.1 ?
C7 C6 H6 . . 122.1 ?
N8 C7 C2 . . 105.00(13) ?
N8 C7 C6 . . 131.53(15) ?
C2 C7 C6 . . 123.47(15) ?
O10 N8 N9 . . 122.37(13) ?
O10 N8 C7 . . 125.79(13) ?
N9 N8 C7 . . 111.77(13) ?
N8 N9 N1 . . 105.66(12) ?
N1 C11 C12 . . 113.08(13) ?
N1 C11 H11A . . 109.0 ?
C12 C11 H11A . . 109.0 ?
N1 C11 H11B . . 109.0 ?
C12 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?
C17 C12 C13 . . 119.98(14) ?
C17 C12 C11 . . 120.02(14) ?
C13 C12 C11 . . 120.00(14) ?
C14 C13 C12 . . 118.82(14) ?
C14 C13 C18 . . 119.21(14) ?
C12 C13 C18 . . 121.96(15) ?
C15 C14 C13 . . 122.03(14) ?
C15 C14 H14 . . 119.0 ?
C13 C14 H14 . . 119.0 ?
C14 C15 C16 . . 118.30(14) ?
C14 C15 C19 . . 120.77(15) ?
C16 C15 C19 . . 120.92(15) ?
C17 C16 C15 . . 121.43(14) ?
C17 C16 H16 . . 119.3 ?
C15 C16 H16 . . 119.3 ?
C16 C17 C12 . . 119.41(14) ?
C16 C17 C20 . . 118.91(14) ?
C12 C17 C20 . . 121.67(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 ?
C15 C19 H19A . . 109.5 ?
C15 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C15 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C17 C20 H20A . . 109.5 ?
C17 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C17 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 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 N9 . 1.3502(18) ?
N1 C2 . 1.358(2) ?
N1 C11 . 1.4713(19) ?
C2 C7 . 1.390(2) ?
C2 C3 . 1.411(2) ?
C3 C4 . 1.362(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.419(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.365(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.392(2) ?
C6 H6 . 0.9500 ?
C7 N8 . 1.387(2) ?
N8 O10 . 1.2842(17) ?
N8 N9 . 1.3166(18) ?
C11 C12 . 1.506(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C17 . 1.400(2) ?
C12 C13 . 1.404(2) ?
C13 C14 . 1.390(2) ?
C13 C18 . 1.508(2) ?
C14 C15 . 1.384(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.393(2) ?
C15 C19 . 1.506(2) ?
C16 C17 . 1.388(2) ?
C16 H16 . 0.9500 ?
C17 C20 . 1.509(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 ?
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
C6 H6 O10 3_665 0.95 2.35 3.190(2) 147.1
C16 H16 O10 2_645 0.95 2.58 3.506(2) 164.8
C18 H18A Cg3 2_745 0.98 2.98 3.810(18) 144
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
N9 N1 C2 C7 . . . . 0.47(17) ?
C11 N1 C2 C7 . . . . 174.51(14) ?
N9 N1 C2 C3 . . . . -179.86(17) ?
C11 N1 C2 C3 . . . . -5.8(3) ?
N1 C2 C3 C4 . . . . -178.70(17) ?
C7 C2 C3 C4 . . . . 0.9(2) ?
C2 C3 C4 C5 . . . . -0.2(3) ?
C3 C4 C5 C6 . . . . -0.6(3) ?
C4 C5 C6 C7 . . . . 0.6(2) ?
N1 C2 C7 N8 . . . . -0.46(16) ?
C3 C2 C7 N8 . . . . 179.81(14) ?
N1 C2 C7 C6 . . . . 178.74(14) ?
C3 C2 C7 C6 . . . . -1.0(2) ?
C5 C6 C7 N8 . . . . 179.14(15) ?
C5 C6 C7 C2 . . . . 0.2(2) ?
C2 C7 N8 O10 . . . . 177.40(14) ?
C6 C7 N8 O10 . . . . -1.7(3) ?
C2 C7 N8 N9 . . . . 0.32(17) ?
C6 C7 N8 N9 . . . . -178.79(15) ?
O10 N8 N9 N1 . . . . -177.24(13) ?
C7 N8 N9 N1 . . . . -0.04(17) ?
C2 N1 N9 N8 . . . . -0.28(17) ?
C11 N1 N9 N8 . . . . -174.86(13) ?
N9 N1 C11 C12 . . . . -35.7(2) ?
C2 N1 C11 C12 . . . . 150.74(15) ?
N1 C11 C12 C17 . . . . 95.32(17) ?
N1 C11 C12 C13 . . . . -85.41(18) ?
C17 C12 C13 C14 . . . . 1.8(2) ?
C11 C12 C13 C14 . . . . -177.43(13) ?
C17 C12 C13 C18 . . . . -177.49(14) ?
C11 C12 C13 C18 . . . . 3.2(2) ?
C12 C13 C14 C15 . . . . -1.6(2) ?
C18 C13 C14 C15 . . . . 177.75(14) ?
C13 C14 C15 C16 . . . . 0.1(2) ?
C13 C14 C15 C19 . . . . -179.23(15) ?
C14 C15 C16 C17 . . . . 1.1(2) ?
C19 C15 C16 C17 . . . . -179.53(16) ?
C15 C16 C17 C12 . . . . -0.8(2) ?
C15 C16 C17 C20 . . . . -179.64(15) ?
C13 C12 C17 C16 . . . . -0.7(2) ?
C11 C12 C17 C16 . . . . 178.61(14) ?
C13 C12 C17 C20 . . . . 178.11(15) ?
C11 C12 C17 C20 . . . . -2.6(2) ?
