#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/14/2201403.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_2201403
loop_
_publ_author_name
'Selvanayagam, S.'
'Rajakannan, V.'
'Velmurugan, D.'
'Dhanasekaran, M.'
'Rajakumar, P.'
'Moon, Jib-Kim'
_publ_section_title
;
 2,6-Bis(N,N'-benzotriazol-1-ylmethyl)pyridine
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1190
_journal_page_last               o1192
_journal_paper_doi               10.1107/S1600536802017567
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C19 H15 N7'
_chemical_formula_moiety         'C19 H15 N7'
_chemical_formula_sum            'C19 H15 N7'
_chemical_formula_weight         341.38
_chemical_name_systematic
;
2,6-Bis(N,N'-benzotriazol-1-ylmethyl)pyridine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.480(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5526(12)
_cell_length_b                   7.9438(9)
_cell_length_c                   14.2666(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      19.69
_cell_volume                     1646.2(2)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990)
;
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Enraf Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3025
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.123
_refine_ls_extinction_coef       0.0058(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0476P)²+0.2138P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0995
_reflns_number_gt                2104
_reflns_number_total             2901
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6166.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2201403
_cod_database_fobs_code          2201403
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.31396(8) 0.18574(16) 0.34202(8) 0.0395(3) Uani d . 1 . . N
N2 0.59335(11) 0.4266(2) 0.29172(12) 0.0647(4) Uani d . 1 . . N
N3 0.53300(10) 0.4351(2) 0.35576(11) 0.0609(4) Uani d . 1 . . N
N4 0.50281(8) 0.27785(18) 0.37372(9) 0.0452(3) Uani d . 1 . . N
N5 0.15538(10) 0.3414(2) 0.01910(10) 0.0572(4) Uani d . 1 . . N
N6 0.13086(9) 0.26556(19) 0.09427(10) 0.0524(4) Uani d . 1 . . N
N7 0.20714(8) 0.21196(16) 0.14464(9) 0.0420(3) Uani d . 1 . . N
C1 0.22398(10) 0.18759(19) 0.31806(10) 0.0398(4) Uani d . 1 . . C
C2 0.16004(11) 0.2606(2) 0.37278(11) 0.0502(4) Uani d . 1 . . C
H2 0.0977 0.2583 0.3542 0.060 Uiso calc R 1 . . H
C3 0.19040(11) 0.3371(2) 0.45555(12) 0.0542(5) Uani d . 1 . . C
H3 0.1489 0.3879 0.4937 0.065 Uiso calc R 1 . . H
C4 0.28293(11) 0.3371(2) 0.48092(11) 0.0463(4) Uani d . 1 . . C
H4 0.3050 0.3881 0.5365 0.056 Uiso calc R 1 . . H
C5 0.34269(10) 0.26032(19) 0.42261(10) 0.0390(4) Uani d . 1 . . C
C6 0.44344(11) 0.2494(2) 0.45017(11) 0.0510(4) Uani d . 1 . . C
H6A 0.4582 0.3317 0.4990 0.061 Uiso calc R 1 . . H
H6B 0.4565 0.1388 0.4765 0.061 Uiso calc R 1 . . H
C7 0.60389(11) 0.2602(2) 0.26876(11) 0.0463(4) Uani d . 1 . . C
C8 0.54604(10) 0.1638(2) 0.32077(10) 0.0400(4) Uani d . 1 . . C
C9 0.54173(11) -0.0105(2) 0.31385(11) 0.0503(4) Uani d . 1 . . C
H9 0.5018 -0.0738 0.3482 0.060 Uiso calc R 1 . . H
C10 0.59956(13) -0.0836(2) 0.25369(12) 0.0579(5) Uani d . 1 . . C
H10 0.5990 -0.2000 0.2469 0.069 Uiso calc R 1 . . H
C11 0.65981(12) 0.0124(3) 0.20173(12) 0.0591(5) Uani d . 1 . . C
H11 0.6986 -0.0422 0.1621 0.071 Uiso calc R 1 . . H
C12 0.66269(12) 0.1827(3) 0.20804(12) 0.0573(5) Uani d . 1 . . C
H12 0.7024 0.2457 0.1732 0.069 Uiso calc R 1 . . H
C13 0.19628(12) 0.1042(2) 0.22585(11) 0.0494(4) Uani d . 1 . . C
H13A 0.2332 0.0036 0.2196 0.059 Uiso calc R 1 . . H
H13B 0.1324 0.0696 0.2264 0.059 Uiso calc R 1 . . H
C14 0.24949(12) 0.3355(2) 0.01881(11) 0.0468(4) Uani d . 1 . . C
C15 0.28371(10) 0.25378(19) 0.09966(10) 0.0417(4) Uani d . 1 . . C
C16 0.37750(12) 0.2283(2) 0.11894(14) 0.0583(5) Uani d . 1 . . C
H16 0.4004 0.1755 0.1736 0.070 Uiso calc R 1 . . H
C17 0.43400(14) 0.2854(3) 0.05292(16) 0.0731(6) Uani d . 1 . . C
H17 0.4972 0.2708 0.0631 0.088 Uiso calc R 1 . . H
C18 0.39997(16) 0.3654(3) -0.02983(15) 0.0735(6) Uani d . 1 . . C
H18 0.4411 0.4011 -0.0731 0.088 Uiso calc R 1 . . H
C19 0.30849(15) 0.3917(2) -0.04813(13) 0.0635(5) Uani d . 1 . . C
H19 0.2861 0.4449 -0.1029 0.076 Uiso calc R 1 . . H
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'
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
C1 N1 C5 117.80(13) ?
N3 N2 C7 107.83(14) ?
N2 N3 N4 108.90(14) ?
N3 N4 C8 110.10(10) ?
N3 N4 C6 120.10(10) y
C8 N4 C6 129.2(2) y
N6 N5 C14 108.13(13) ?
N5 N6 N7 109.07(13) ?
N6 N7 C15 110.00(10) ?
N6 N7 C13 118.80(10) y
C15 N7 C13 130.60(10) y
N1 C1 C2 123.08(14) ?
N1 C1 C13 115.19(14) ?
C2 C1 C13 121.73(14) ?
C3 C2 C1 118.62(15) ?
C3 C2 H2 120.7 ?
C1 C2 H2 120.7 ?
C4 C3 C2 119.00(15) ?
C4 C3 H3 120.5 ?
C2 C3 H3 120.5 ?
C3 C4 C5 118.96(15) ?
C3 C4 H4 120.5 ?
C5 C4 H4 120.5 ?
N1 C5 C4 122.53(14) ?
N1 C5 C6 116.76(13) ?
C4 C5 C6 120.64(14) ?
N4 C6 C5 114.35(13) ?
N4 C6 H6A 108.7 ?
C5 C6 H6A 108.7 ?
N4 C6 H6B 108.7 ?
C5 C6 H6B 108.7 ?
H6A C6 H6B 107.6 ?
N2 C7 C8 108.89(14) ?
N2 C7 C12 130.80(16) ?
C8 C7 C12 120.25(16) ?
N4 C8 C7 104.26(14) ?
N4 C8 C9 133.14(15) ?
C7 C8 C9 122.59(15) ?
C10 C9 C8 116.17(16) ?
C10 C9 H9 121.9 ?
C8 C9 H9 121.9 ?
C9 C10 C11 121.85(18) ?
C9 C10 H10 119.1 ?
C11 C10 H10 119.1 ?
C12 C11 C10 121.56(17) ?
C12 C11 H11 119.2 ?
C10 C11 H11 119.2 ?
C11 C12 C7 117.56(17) ?
C11 C12 H12 121.2 ?
C7 C12 H12 121.2 ?
N7 C13 C1 113.57(12) ?
N7 C13 H13A 108.9 ?
C1 C13 H13A 108.9 ?
N7 C13 H13B 108.9 ?
C1 C13 H13B 108.9 ?
H13A C13 H13B 107.7 ?
N5 C14 C15 108.75(15) ?
N5 C14 C19 130.34(16) ?
C15 C14 C19 120.88(16) ?
N7 C15 C14 104.07(13) ?
N7 C15 C16 133.91(15) ?
C14 C15 C16 122.02(16) ?
C17 C16 C15 116.13(17) ?
C17 C16 H16 121.9 ?
C15 C16 H16 121.9 ?
C16 C17 C18 122.28(19) ?
C16 C17 H17 118.9 ?
C18 C17 H17 118.9 ?
C19 C18 C17 121.54(19) ?
C19 C18 H18 119.2 ?
C17 C18 H18 119.2 ?
C18 C19 C14 117.13(18) ?
C18 C19 H19 121.4 ?
C14 C19 H19 121.4 ?
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 C1 . 1.3332(19) ?
N1 C5 . 1.3377(19) ?
N2 N3 . 1.307(2) y
N2 C7 . 1.373(2) y
N3 N4 . 1.354(2) y
N4 C8 . 1.358(2) y
N4 C6 . 1.4496(19) y
N5 N6 . 1.299(2) y
N5 C14 . 1.371(2) y
N6 N7 . 1.3538(18) y
N7 C15 . 1.3603(19) y
N7 C13 . 1.457(2) y
C1 C2 . 1.378(2) ?
C1 C13 . 1.506(2) ?
C2 C3 . 1.377(2) ?
C2 H2 . 0.93 ?
C3 C4 . 1.373(2) ?
C3 H3 . 0.93 ?
C4 C5 . 1.382(2) ?
C4 H4 . 0.93 ?
C5 C6 . 1.497(2) ?
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
C7 C8 . 1.386(2) y
C7 C12 . 1.397(2) y
C8 C9 . 1.389(2) y
C9 C10 . 1.368(2) y
C9 H9 . 0.93 ?
C10 C11 . 1.406(3) y
C10 H10 . 0.93 ?
C11 C12 . 1.357(3) y
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C14 C15 . 1.389(2) y
C14 C19 . 1.396(2) y
C15 C16 . 1.391(2) y
C16 C17 . 1.365(3) y
C16 H16 . 0.93 ?
C17 C18 . 1.404(3) y
C17 H17 . 0.93 ?
C18 C19 . 1.357(3) y
C18 H18 . 0.93 ?
C19 H19 . 0.93 ?
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
C16 H16 N1 . 0.93 2.78 3.385(2) 124
C6 H6A N3 3_666 0.97 2.78 3.734(2) 170
C13 H13B N3 2_545 0.97 2.82 3.718(2) 154
C9 H9 N6 2_545 0.93 2.49 3.405(2) 166
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
C7 N2 N3 N4 -1.10(19) ?
N2 N3 N4 C8 1.00(18) ?
N2 N3 N4 C6 172.69(14) ?
C14 N5 N6 N7 1.04(18) ?
N5 N6 N7 C15 -0.53(18) ?
N5 N6 N7 C13 -172.11(13) ?
C5 N1 C1 C2 -0.8(2) ?
C5 N1 C1 C13 179.01(13) ?
N1 C1 C2 C3 0.8(2) ?
C13 C1 C2 C3 -178.96(15) ?
C1 C2 C3 C4 -0.4(3) ?
C2 C3 C4 C5 -0.1(3) ?
C1 N1 C5 C4 0.3(2) ?
C1 N1 C5 C6 177.19(14) ?
C3 C4 C5 N1 0.1(2) ?
C3 C4 C5 C6 -176.68(16) ?
N3 N4 C6 C5 91.04(18) ?
C8 N4 C6 C5 -99.05(17) y
N1 C5 C6 N4 43.1(2) y
C4 C5 C6 N4 -139.94(16) ?
N3 N2 C7 C8 0.81(19) ?
N3 N2 C7 C12 -176.56(17) ?
N3 N4 C8 C7 -0.47(16) ?
C6 N4 C8 C7 -171.18(14) ?
N3 N4 C8 C9 178.50(16) ?
C6 N4 C8 C9 7.8(3) ?
N2 C7 C8 N4 -0.20(17) ?
C12 C7 C8 N4 177.50(14) ?
N2 C7 C8 C9 -179.31(15) ?
C12 C7 C8 C9 -1.6(2) ?
N4 C8 C9 C10 -177.56(15) ?
C7 C8 C9 C10 1.3(2) ?
C8 C9 C10 C11 -0.1(2) ?
C9 C10 C11 C12 -0.8(3) ?
C10 C11 C12 C7 0.4(3) ?
N2 C7 C12 C11 177.83(18) ?
C8 C7 C12 C11 0.7(2) ?
N6 N7 C13 C1 -111.93(15) ?
C15 N7 C13 C1 78.5(2) y
N1 C1 C13 N7 -82.23(17) ?
C2 C1 C13 N7 97.54(18) y
N6 N5 C14 C15 -1.17(19) ?
N6 N5 C14 C19 176.73(17) ?
N6 N7 C15 C14 -0.20(17) ?
C13 N7 C15 C14 170.09(14) ?
N6 N7 C15 C16 -179.11(18) ?
C13 N7 C15 C16 -8.8(3) ?
N5 C14 C15 N7 0.82(17) ?
C19 C14 C15 N7 -177.31(15) ?
N5 C14 C15 C16 179.89(15) ?
C19 C14 C15 C16 1.8(2) ?
N7 C15 C16 C17 177.54(18) ?
C14 C15 C16 C17 -1.2(3) ?
C15 C16 C17 C18 0.0(3) ?
C16 C17 C18 C19 0.7(3) ?
C17 C18 C19 C14 -0.1(3) ?
N5 C14 C19 C18 -178.7(2) ?
C15 C14 C19 C18 -1.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21132117
