#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/13/2221301.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_2221301
loop_
_publ_author_name
'Ravindran Durai Nayagam, B.'
'Jebas, Samuel Robinson'
'Daisy, Caroline'
'Schollmeyer, Dieter'
_publ_section_title
1,1'-[2,3,5,6-Tetramethyl-p-phenylenebis(methyleneoxy)]di-1H-benzotriazole
_journal_coeditor_code           BT2912
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o918
_journal_paper_doi               10.1107/S1600536809010782
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C24 H24 N6 O2'
_chemical_formula_moiety         'C24 H24 N6 O2'
_chemical_formula_sum            'C24 H24 N6 O2'
_chemical_formula_weight         428.49
_chemical_name_systematic
1,1'-[2,3,5,6-Tetramethyl-p-phenylenebis(methyleneoxy)]di-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                 110.770(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.3895(6)
_cell_length_b                   7.5960(2)
_cell_length_c                   15.7471(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      70
_cell_measurement_theta_min      65
_cell_volume                     1050.13(11)
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2075
_diffrn_reflns_theta_full        69.95
_diffrn_reflns_theta_max         69.95
_diffrn_reflns_theta_min         5.04
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  0.8730
_exptl_absorpt_correction_T_min  0.7071
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(CORINC; Draeger & Gattow, 1971)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.330
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0519
_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)+(0.0832P)²+0.5P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1450
_refine_ls_wR_factor_ref         0.1465
_reflns_number_gt                1905
_reflns_number_total             1996
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2912.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221301
_cod_database_fobs_code          2221301
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 0.25022(16) -0.07614(18) 0.47932(9) 0.0302(3) Uani d . 1 . .
N N2 0.17398(19) -0.1201(2) 0.53429(10) 0.0385(4) Uani d . 1 . .
N N3 0.08837(19) -0.2555(2) 0.49841(11) 0.0408(4) Uani d . 1 . .
C C4 0.10897(19) -0.2985(2) 0.41828(12) 0.0317(4) Uani d . 1 . .
C C5 0.0438(2) -0.4308(2) 0.35473(14) 0.0396(4) Uani d . 1 . .
H H5 -0.0276 -0.5118 0.3627 0.047 Uiso calc R 1 . .
C C6 0.0873(2) -0.4389(3) 0.28015(13) 0.0408(5) Uani d . 1 . .
H H6 0.0438 -0.5264 0.2353 0.049 Uiso calc R 1 . .
C C7 0.1948(2) -0.3209(2) 0.26842(12) 0.0380(4) Uani d . 1 . .
H H7 0.2212 -0.3309 0.2157 0.046 Uiso calc R 1 . .
C C8 0.26238(19) -0.1922(2) 0.33068(12) 0.0321(4) Uani d . 1 . .
H H8 0.3367 -0.1146 0.3235 0.039 Uiso calc R 1 . .
C C9 0.21514(17) -0.1820(2) 0.40554(11) 0.0270(4) Uani d . 1 . .
O O10 0.34983(13) 0.06259(15) 0.50086(8) 0.0317(3) Uani d . 1 . .
C C11 0.27184(18) 0.2246(2) 0.45748(11) 0.0296(4) Uani d . 1 . .
H H11A 0.1907 0.2561 0.4812 0.036 Uiso calc R 1 . .
H H11B 0.2253 0.2087 0.3909 0.036 Uiso calc R 1 . .
C C12 0.39164(17) 0.3661(2) 0.48003(10) 0.0248(4) Uani d . 1 . .
C C13 0.47071(18) 0.3997(2) 0.42060(10) 0.0259(4) Uani d . 1 . .
C C14 0.42305(17) 0.4639(2) 0.55983(10) 0.0255(4) Uani d . 1 . .
C C15 0.4428(2) 0.2893(2) 0.33658(12) 0.0381(4) Uani d . 1 . .
H H15A 0.3797 0.3554 0.2830 0.057 Uiso calc R 1 . .
H H15B 0.3901 0.1806 0.3416 0.057 Uiso calc R 1 . .
H H15C 0.5404 0.2601 0.3305 0.057 Uiso calc R 1 . .
C C16 0.3446(2) 0.4206(3) 0.62620(13) 0.0397(5) Uani d . 1 . .
H H16A 0.4183 0.4283 0.6884 0.060 Uiso calc R 1 . .
H H16B 0.3032 0.3009 0.6147 0.060 Uiso calc R 1 . .
H H16C 0.2616 0.5044 0.6185 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(14) ?
N2 N1 O10 . . 120.24(13) ?
C9 N1 O10 . . 127.34(13) ?
N3 N2 N1 . . 107.67(14) ?
N2 N3 C4 . . 108.54(14) ?
N3 C4 C5 . . 131.05(16) ?
N3 C4 C9 . . 108.58(15) ?
C5 C4 C9 . . 120.37(16) ?
C6 C5 C4 . . 117.17(16) ?
C6 C5 H5 . . 121.4 ?
C4 C5 H5 . . 121.4 ?
C5 C6 C7 . . 121.79(17) ?
C5 C6 H6 . . 119.1 ?
C7 C6 H6 . . 119.1 ?
C8 C7 C6 . . 122.08(16) ?
C8 C7 H7 . . 119.0 ?
C6 C7 H7 . . 119.0 ?
C7 C8 C9 . . 115.90(15) ?
C7 C8 H8 . . 122.1 ?
C9 C8 H8 . . 122.1 ?
N1 C9 C4 . . 102.80(14) ?
N1 C9 C8 . . 134.53(15) ?
C4 C9 C8 . . 122.67(16) ?
N1 O10 C11 . . 110.19(11) ?
O10 C11 C12 . . 106.29(12) ?
O10 C11 H11A . . 110.5 ?
C12 C11 H11A . . 110.5 ?
O10 C11 H11B . . 110.5 ?
C12 C11 H11B . . 110.5 ?
H11A C11 H11B . . 108.7 ?
C14 C12 C13 . . 120.49(15) ?
C14 C12 C11 . . 119.57(14) ?
C13 C12 C11 . . 119.94(14) ?
C14 C13 C12 3_666 . 119.49(14) ?
C14 C13 C15 3_666 . 119.67(14) ?
C12 C13 C15 . . 120.84(15) ?
C13 C14 C12 3_666 . 119.98(13) ?
C13 C14 C16 3_666 . 119.62(14) ?
C12 C14 C16 . . 120.38(15) ?
C13 C15 H15A . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C13 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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 . 1.3465(18) ?
N1 C9 . 1.354(2) ?
N1 O10 . 1.3694(17) ?
N2 N3 . 1.304(2) ?
N3 C4 . 1.382(2) ?
C4 C5 . 1.397(3) ?
C4 C9 . 1.400(2) ?
C5 C6 . 1.375(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.410(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.370(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.401(2) ?
C8 H8 . 0.9500 ?
O10 C11 . 1.4707(19) ?
C11 C12 . 1.504(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C14 . 1.399(2) ?
C12 C13 . 1.409(2) ?
C13 C14 3_666 1.394(2) ?
C13 C15 . 1.509(2) ?
C14 C13 3_666 1.394(2) ?
C14 C16 . 1.5129(19) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 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 Cg2 2_545 0.95 2.82 3.700(2) 154
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 . . . . 0.3(2) ?
O10 N1 N2 N3 . . . . -179.78(14) ?
N1 N2 N3 C4 . . . . -0.5(2) ?
N2 N3 C4 C5 . . . . -179.59(18) ?
N2 N3 C4 C9 . . . . 0.5(2) ?
N3 C4 C5 C6 . . . . 179.40(18) ?
C9 C4 C5 C6 . . . . -0.7(3) ?
C4 C5 C6 C7 . . . . 0.9(3) ?
C5 C6 C7 C8 . . . . 0.3(3) ?
C6 C7 C8 C9 . . . . -1.6(3) ?
N2 N1 C9 C4 . . . . -0.03(18) ?
O10 N1 C9 C4 . . . . -179.88(14) ?
N2 N1 C9 C8 . . . . -179.42(18) ?
O10 N1 C9 C8 . . . . 0.7(3) ?
N3 C4 C9 N1 . . . . -0.29(18) ?
C5 C4 C9 N1 . . . . 179.80(15) ?
N3 C4 C9 C8 . . . . 179.20(15) ?
C5 C4 C9 C8 . . . . -0.7(3) ?
C7 C8 C9 N1 . . . . -178.85(17) ?
C7 C8 C9 C4 . . . . 1.9(2) ?
N2 N1 O10 C11 . . . . -92.95(16) ?
C9 N1 O10 C11 . . . . 86.90(18) ?
N1 O10 C11 C12 . . . . -176.52(11) ?
O10 C11 C12 C14 . . . . -88.45(17) ?
O10 C11 C12 C13 . . . . 91.90(16) ?
C14 C12 C13 C14 . . . 3_666 -2.3(3) ?
C11 C12 C13 C14 . . . 3_666 177.30(13) ?
C14 C12 C13 C15 . . . . 177.14(15) ?
C11 C12 C13 C15 . . . . -3.2(2) ?
C13 C12 C14 C13 . . . 3_666 2.4(3) ?
C11 C12 C14 C13 . . . 3_666 -177.29(13) ?
C13 C12 C14 C16 . . . . -176.44(15) ?
C11 C12 C14 C16 . . . . 3.9(2) ?
