#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/45/2204594.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_2204594
loop_
_publ_author_name
'S. Selvanayagam'
'D. Velmurugan'
'K. Ravikumar'
'M. Dhanasekaran'
'P. Rajakumar'
_publ_section_title
;
 Benzyl 3,5-bis(1H-benzotriazol-1-ylmethyl)phenyl ether
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2165
_journal_page_last               o2167
_journal_paper_doi               10.1107/S1600536804027138
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C27 H22 N6 O'
_chemical_formula_moiety         'C27 H22 N6 O'
_chemical_formula_sum            'C27 H22 N6 O'
_chemical_formula_weight         446.51
_chemical_name_systematic
;
Benzyl 3,5-bis(1H-benzotriazol-1-ylmethyl)phenyl ether
;
_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                 98.780(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5494(9)
_cell_length_b                   9.5609(10)
_cell_length_c                   27.627(3)
_cell_measurement_reflns_used    4863
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.28
_cell_volume                     2231.8(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            13153
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0493
_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)+(0.0648P)²+0.3501P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                3847
_reflns_number_total             5095
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6299.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2204594
_cod_database_fobs_code          2204594
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_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_type_symbol
C1 -0.24900(17) 0.38762(16) 0.24547(5) 0.0437(3) Uani d . 1 C
H1 -0.3078 0.3925 0.2143 0.052 Uiso calc R 1 H
C2 -0.11705(17) 0.30081(16) 0.25415(5) 0.0425(3) Uani d . 1 C
C3 -0.03168(17) 0.29322(15) 0.30041(5) 0.0418(3) Uani d . 1 C
H3 0.0567 0.2355 0.3063 0.050 Uiso calc R 1 H
C4 -0.07633(17) 0.37111(14) 0.33847(5) 0.0395(3) Uani d . 1 C
C5 -0.20615(17) 0.45911(15) 0.32980(5) 0.0400(3) Uani d . 1 C
H5 -0.2351 0.5128 0.3551 0.048 Uiso calc R 1 H
C6 -0.29294(16) 0.46661(14) 0.28305(5) 0.0373(3) Uani d . 1 C
C7 -0.0596(2) 0.2137(2) 0.21448(5) 0.0651(5) Uani d . 1 C
H7A 0.0455 0.2451 0.2104 0.078 Uiso calc R 1 H
H7B -0.0511 0.1170 0.2252 0.078 Uiso calc R 1 H
C8 -0.29272(18) 0.27637(16) 0.09726(5) 0.0441(3) Uani d . 1 C
C9 -0.3411(2) 0.3578(2) 0.05562(6) 0.0607(5) Uani d . 1 C
H9 -0.4184 0.3266 0.0306 0.073 Uiso calc R 1 H
C10 -0.2709(3) 0.4835(2) 0.05331(7) 0.0752(6) Uani d . 1 C
H10 -0.3006 0.5399 0.0260 0.090 Uiso calc R 1 H
C11 -0.1554(3) 0.5310(2) 0.09063(9) 0.0794(6) Uani d . 1 C
H11 -0.1116 0.6191 0.0877 0.095 Uiso calc R 1 H
C12 -0.1039(2) 0.45367(19) 0.13129(7) 0.0643(5) Uani d . 1 C
H12 -0.0255 0.4855 0.1559 0.077 Uiso calc R 1 H
C13 -0.17597(17) 0.32371(15) 0.13371(5) 0.0412(3) Uani d . 1 C
C14 -0.43529(18) 0.56300(17) 0.27563(5) 0.0492(4) Uani d . 1 C
H14A -0.5010 0.5426 0.3004 0.059 Uiso calc R 1 H
H14B -0.3989 0.6588 0.2804 0.059 Uiso calc R 1 H
C15 -0.6332(2) 0.56075(17) 0.15099(6) 0.0535(4) Uani d . 1 C
C16 -0.6576(3) 0.6103(2) 0.10278(6) 0.0711(6) Uani d . 1 C
H16 -0.7328 0.5701 0.0790 0.085 Uiso calc R 1 H
C17 -0.5675(3) 0.7193(2) 0.09213(6) 0.0728(6) Uani d . 1 C
H17 -0.5819 0.7544 0.0604 0.087 Uiso calc R 1 H
C18 -0.4536(2) 0.7805(2) 0.12741(7) 0.0663(5) Uani d . 1 C
H18 -0.3936 0.8545 0.1184 0.080 Uiso calc R 1 H
C19 -0.4280(2) 0.73474(17) 0.17482(6) 0.0532(4) Uani d . 1 C
H19 -0.3526 0.7758 0.1984 0.064 Uiso calc R 1 H
C20 -0.52089(17) 0.62330(15) 0.18589(5) 0.0418(3) Uani d . 1 C
C21 -0.0221(2) 0.42788(19) 0.42365(5) 0.0586(5) Uani d . 1 C
H21A -0.1329 0.4157 0.4265 0.070 Uiso calc R 1 H
H21B -0.0025 0.5267 0.4194 0.070 Uiso calc R 1 H
C22 0.08034(19) 0.37432(16) 0.46888(5) 0.0473(4) Uani d . 1 C
C23 0.2305(2) 0.42702(19) 0.48294(5) 0.0543(4) Uani d . 1 C
H23 0.2702 0.4940 0.4637 0.065 Uiso calc R 1 H
C24 0.3224(2) 0.3811(2) 0.52547(6) 0.0600(4) Uani d . 1 C
H24 0.4230 0.4182 0.5349 0.072 Uiso calc R 1 H
C25 0.2656(2) 0.28076(19) 0.55380(5) 0.0592(5) Uani d . 1 C
H25 0.3276 0.2497 0.5824 0.071 Uiso calc R 1 H
C26 0.1173(2) 0.22670(19) 0.53981(6) 0.0607(5) Uani d . 1 C
H26 0.0787 0.1583 0.5588 0.073 Uiso calc R 1 H
C27 0.0253(2) 0.27352(18) 0.49761(6) 0.0554(4) Uani d . 1 C
H27 -0.0755 0.2365 0.4884 0.066 Uiso calc R 1 H
N1 -0.16053(15) 0.22001(13) 0.16754(4) 0.0461(3) Uani d . 1 N
N2 -0.26320(18) 0.11547(14) 0.15298(5) 0.0570(4) Uani d . 1 N
N3 -0.34235(18) 0.14762(15) 0.11063(5) 0.0585(4) Uani d . 1 N
N4 -0.53119(14) 0.55107(13) 0.22765(4) 0.0456(3) Uani d . 1 N
N5 -0.64182(17) 0.44953(16) 0.21882(6) 0.0654(4) Uani d . 1 N
N6 -0.70412(19) 0.45445(17) 0.17274(6) 0.0741(5) Uani d . 1 N
O1 0.01518(13) 0.35108(12) 0.38279(3) 0.0545(3) Uani d . 1 O
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
_geom_angle_publ_flag
C6 C1 C2 120.19(12) ?
C6 C1 H1 119.9 ?
C2 C1 H1 119.9 ?
C3 C2 C1 119.57(12) ?
C3 C2 C7 117.31(13) ?
C1 C2 C7 123.12(12) ?
C2 C3 C4 120.51(13) ?
C2 C3 H3 119.7 ?
C4 C3 H3 119.7 ?
O1 C4 C5 125.19(12) ?
O1 C4 C3 114.75(12) ?
C5 C4 C3 120.06(12) ?
C4 C5 C6 119.50(12) ?
C4 C5 H5 120.3 ?
C6 C5 H5 120.3 ?
C1 C6 C5 120.16(12) ?
C1 C6 C14 122.39(12) ?
C5 C6 C14 117.45(12) ?
N1 C7 C2 114.26(13) ?
N1 C7 H7A 108.7 ?
C2 C7 H7A 108.7 ?
N1 C7 H7B 108.7 ?
C2 C7 H7B 108.7 ?
H7A C7 H7B 107.6 ?
N3 C8 C13 108.47(13) ?
N3 C8 C9 131.03(14) ?
C13 C8 C9 120.50(15) ?
C10 C9 C8 117.18(17) ?
C10 C9 H9 121.4 ?
C8 C9 H9 121.4 ?
C9 C10 C11 121.78(18) ?
C9 C10 H10 119.1 ?
C11 C10 H10 119.1 ?
C12 C11 C10 122.55(18) ?
C12 C11 H11 118.7 ?
C10 C11 H11 118.7 ?
C11 C12 C13 115.76(17) ?
C11 C12 H12 122.1 ?
C13 C12 H12 122.1 ?
N1 C13 C8 104.27(13) ?
N1 C13 C12 133.51(15) ?
C8 C13 C12 122.21(15) ?
N4 C14 C6 113.92(12) ?
N4 C14 H14A 108.8 ?
C6 C14 H14A 108.8 ?
N4 C14 H14B 108.8 ?
C6 C14 H14B 108.8 ?
H14A C14 H14B 107.7 ?
N6 C15 C20 108.70(14) ?
N6 C15 C16 131.16(16) ?
C20 C15 C16 120.15(16) ?
C17 C16 C15 117.40(16) ?
C17 C16 H16 121.3 ?
C15 C16 H16 121.3 ?
C16 C17 C18 121.99(17) ?
C16 C17 H17 119.0 ?
C18 C17 H17 119.0 ?
C19 C18 C17 121.83(18) ?
C19 C18 H18 119.1 ?
C17 C18 H18 119.1 ?
C18 C19 C20 116.29(15) ?
C18 C19 H19 121.9 ?
C20 C19 H19 121.9 ?
N4 C20 C15 104.08(14) ?
N4 C20 C19 133.58(14) ?
C15 C20 C19 122.34(14) ?
O1 C21 C22 108.14(12) ?
O1 C21 H21A 110.1 ?
C22 C21 H21A 110.1 ?
O1 C21 H21B 110.1 ?
C22 C21 H21B 110.1 ?
H21A C21 H21B 108.4 ?
C27 C22 C23 118.63(14) ?
C27 C22 C21 120.74(16) ?
C23 C22 C21 120.62(16) ?
C22 C23 C24 120.51(16) ?
C22 C23 H23 119.7 ?
C24 C23 H23 119.7 ?
C25 C24 C23 120.14(17) ?
C25 C24 H24 119.9 ?
C23 C24 H24 119.9 ?
C26 C25 C24 119.73(15) ?
C26 C25 H25 120.1 ?
C24 C25 H25 120.1 ?
C25 C26 C27 120.06(17) ?
C25 C26 H26 120.0 ?
C27 C26 H26 120.0 ?
C22 C27 C26 120.92(16) ?
C22 C27 H27 119.5 ?
C26 C27 H27 119.5 ?
N2 N1 C13 110.22(11) ?
N2 N1 C7 120.60(10) y
C13 N1 C7 129.20(10) y
N3 N2 N1 108.64(12) ?
N2 N3 C8 108.40(12) ?
N5 N4 C20 110.24(12) ?
N5 N4 C14 120.20(10) y
C20 N4 C14 129.40(10) y
N6 N5 N4 108.71(13) ?
N5 N6 C15 108.26(13) ?
C4 O1 C21 118.24(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.3815(19) ?
C1 C2 1.392(2) ?
C1 H1 0.9300 ?
C2 C3 1.3736(18) ?
C2 C7 1.517(2) y
C3 C4 1.3886(19) ?
C3 H3 0.9300 ?
C4 O1 1.3624(15) y
C4 C5 1.384(2) ?
C5 C6 1.3896(17) ?
C5 H5 0.9300 ?
C6 C14 1.515(2) y
C7 N1 1.4450(18) y
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 N3 1.371(2) y
C8 C13 1.381(2) .
C8 C9 1.398(2) .
C9 C10 1.350(3) .
C9 H9 0.9300 ?
C10 C11 1.391(3) .
C10 H10 0.9300 ?
C11 C12 1.361(3) .
C11 H11 0.9300 ?
C12 C13 1.393(2) .
C12 H12 0.9300 ?
C13 N1 1.355(2) y
C14 N4 1.453(2) y
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 N6 1.369(2) y
C15 C20 1.388(2) .
C15 C16 1.399(2) .
C16 C17 1.354(3) .
C16 H16 0.9300 ?
C17 C18 1.397(3) .
C17 H17 0.9300 ?
C18 C19 1.366(2) .
C18 H18 0.9300 ?
C19 C20 1.391(2) .
C19 H19 0.9300 ?
C20 N4 1.359(2) y
C21 O1 1.423(2) y
C21 C22 1.502(2) y
C21 H21A 0.9700 ?
C21 H21B 0.9700 ?
C22 C27 1.377(2) ?
C22 C23 1.379(2) ?
C23 C24 1.382(2) ?
C23 H23 0.9300 ?
C24 C25 1.373(3) ?
C24 H24 0.9300 ?
C25 C26 1.369(3) ?
C25 H25 0.9300 ?
C26 C27 1.378(2) ?
C26 H26 0.9300 ?
C27 H27 0.9300 ?
N1 N2 1.350(2) y
N2 N3 1.296(2) y
N4 N5 1.351(2) y
N5 N6 1.304(2) y
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
C1 H1 N1 . 0.93 2.54 2.876(2) 102
C1 H1 N4 . 0.93 2.51 2.854(2) 102
C11 H11 O1 2 0.93 2.46 3.327(2) 155
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
_geom_torsion_publ_flag
C6 C1 C2 C3 0.6(2) ?
C6 C1 C2 C7 -178.57(16) ?
C1 C2 C3 C4 0.2(2) ?
C7 C2 C3 C4 179.38(15) ?
C2 C3 C4 O1 178.12(14) ?
C2 C3 C4 C5 -1.1(2) ?
O1 C4 C5 C6 -177.85(13) ?
C3 C4 C5 C6 1.3(2) ?
C2 C1 C6 C5 -0.4(2) ?
C2 C1 C6 C14 179.89(15) ?
C4 C5 C6 C1 -0.5(2) ?
C4 C5 C6 C14 179.18(14) ?
C3 C2 C7 N1 176.3(2) y
C1 C2 C7 N1 -4.5(3) ?
N3 C8 C9 C10 178.72(18) ?
C13 C8 C9 C10 -1.0(2) ?
C8 C9 C10 C11 -0.1(3) ?
C9 C10 C11 C12 1.1(3) ?
C10 C11 C12 C13 -0.9(3) ?
N3 C8 C13 N1 0.14(16) ?
C9 C8 C13 N1 179.91(14) ?
N3 C8 C13 C12 -178.60(15) ?
C9 C8 C13 C12 1.2(2) ?
C11 C12 C13 N1 -178.51(17) ?
C11 C12 C13 C8 -0.2(2) ?
C1 C6 C14 N4 7.4(2) y
C5 C6 C14 N4 -172.34(13) ?
N6 C15 C16 C17 180.0(2) ?
C20 C15 C16 C17 0.4(3) ?
C15 C16 C17 C18 0.3(3) ?
C16 C17 C18 C19 -0.7(3) ?
C17 C18 C19 C20 0.4(3) ?
N6 C15 C20 N4 -0.56(18) ?
C16 C15 C20 N4 179.10(16) ?
N6 C15 C20 C19 179.63(15) ?
C16 C15 C20 C19 -0.7(2) ?
C18 C19 C20 N4 -179.44(16) ?
C18 C19 C20 C15 0.3(2) ?
O1 C21 C22 C27 -95.25(18) ?
O1 C21 C22 C23 85.93(19) ?
C27 C22 C23 C24 -1.1(2) ?
C21 C22 C23 C24 177.76(14) ?
C22 C23 C24 C25 0.9(3) ?
C23 C24 C25 C26 -0.2(3) ?
C24 C25 C26 C27 -0.4(3) ?
C23 C22 C27 C26 0.5(2) ?
C21 C22 C27 C26 -178.32(14) ?
C25 C26 C27 C22 0.2(3) ?
C8 C13 N1 N2 -0.63(16) ?
C12 C13 N1 N2 177.89(17) ?
C8 C13 N1 C7 -177.59(14) ?
C12 C13 N1 C7 0.9(3) ?
C2 C7 N1 N2 -100.70(18) ?
C2 C7 N1 C13 76.0(2) ?
C13 N1 N2 N3 0.93(17) ?
C7 N1 N2 N3 178.19(13) ?
N1 N2 N3 C8 -0.82(18) ?
C13 C8 N3 N2 0.42(18) ?
C9 C8 N3 N2 -179.31(17) ?
C15 C20 N4 N5 0.60(17) ?
C19 C20 N4 N5 -179.62(16) ?
C15 C20 N4 C14 175.41(14) ?
C19 C20 N4 C14 -4.8(3) ?
C6 C14 N4 N5 83.39(18) ?
C6 C14 N4 C20 -90.97(18) ?
C20 N4 N5 N6 -0.43(19) ?
C14 N4 N5 N6 -175.79(14) ?
N4 N5 N6 C15 0.1(2) ?
C20 C15 N6 N5 0.3(2) ?
C16 C15 N6 N5 -179.28(19) ?
C5 C4 O1 C21 -1.3(2) ?
C3 C4 O1 C21 179.54(15) ?
C22 C21 O1 C4 172.60(10) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130260
