#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/96/2209665.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_2209665
loop_
_publ_author_name
'G. Senthil Kumar'
'K. Chinnakali'
'M. Gayatri Swaroop'
'P. Rajakumar'
'Hoong-Kun Fun'
_publ_section_title
1,9,26-Triazahexacyclo[17.6.1.1^3,7^.1^9,16^.0^10,15^.0^20,25^]pentacosa-3,5,7(26),10(15),11,13,16(27),17,19(28),20(25),21,23-dodecaene
_journal_coeditor_code           SJ2088
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2608
_journal_page_last               o2610
_journal_paper_doi               10.1107/S1600536806020514
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C25 H19 N3'
_chemical_formula_moiety         'C25 H19 N3'
_chemical_formula_sum            'C25 H19 N3'
_chemical_formula_weight         361.43
_chemical_name_systematic
;
1,9,26-Triazahexacyclo[17.6.1.1^3,7^.1^9,16^.0^10,15^.0^20,25^]
pentacosa-3,5,7(26),10(15),11,13,16(27),17,19(28),20(25),21,23-dodecaene
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 113.994(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.9027(7)
_cell_length_b                   11.3107(3)
_cell_length_c                   8.7157(5)
_cell_measurement_reflns_used    6564
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      37.100
_cell_measurement_theta_min      2.627
_cell_volume                     1792.48(14)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Bruker SMART APEX2 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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0122
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24681
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_correction_T_min  0.9173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.305
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0566P)²+1.0129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                1927
_reflns_number_total             2064
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2088.cif
_cod_data_source_block           I
_cod_original_cell_volume        1792.48(13)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2209665
_cod_database_fobs_code          2209665
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
N N1 -0.11929(4) 0.18374(7) 0.06151(10) 0.0179(2) Uani d . 1
N N2 0.0000 0.05214(10) 0.2500 0.0176(2) Uani d S 1
C C1 -0.07190(5) 0.27541(9) 0.07460(12) 0.0201(2) Uani d . 1
H H1 -0.0361(7) 0.2678(12) 0.0245(16) 0.026(3) Uiso d . 1
C C2 -0.08178(5) 0.36627(8) 0.16726(12) 0.0194(2) Uani d . 1
C C3 -0.13917(5) 0.32878(8) 0.21660(12) 0.0180(2) Uani d . 1
C C4 -0.17396(5) 0.38041(9) 0.31150(12) 0.0211(2) Uani d . 1
H H4 -0.1596(7) 0.4604(13) 0.3603(17) 0.028(3) Uiso d . 1
C C5 -0.22839(6) 0.31735(9) 0.33640(13) 0.0234(2) Uani d . 1
H H5 -0.2539(7) 0.3512(12) 0.4035(17) 0.029(3) Uiso d . 1
C C6 -0.24860(6) 0.20292(10) 0.26929(13) 0.0229(2) Uani d . 1
H H6 -0.2881(8) 0.1597(13) 0.2865(18) 0.035(4) Uiso d . 1
C C7 -0.21486(5) 0.14955(9) 0.17644(12) 0.0198(2) Uani d . 1
H H7 -0.2295(7) 0.0718(12) 0.1290(16) 0.023(3) Uiso d . 1
C C8 -0.16023(5) 0.21329(8) 0.15079(11) 0.0173(2) Uani d . 1
C C9 -0.11353(5) 0.06674(8) 0.00008(12) 0.0196(2) Uani d . 1
H H9B -0.0998(7) 0.0764(11) -0.0976(16) 0.020(3) Uiso d . 1
H H9A -0.1621(7) 0.0269(11) -0.0388(15) 0.021(3) Uiso d . 1
C C10 -0.05444(5) -0.00786(8) 0.13195(11) 0.0169(2) Uani d . 1
C C11 -0.05675(5) -0.13101(9) 0.12605(12) 0.0201(2) Uani d . 1
H H11 -0.0970(7) -0.1715(12) 0.0387(16) 0.025(3) Uiso d . 1
C C12 0.0000 -0.19247(12) 0.2500 0.0226(3) Uani d S 1
H H12 0.0000 -0.2786(19) 0.2500 0.032(5) Uiso d S 1
C C13 -0.03684(6) 0.47429(9) 0.21611(14) 0.0239(2) Uani d . 1
H H13 -0.0640(7) 0.5515(12) 0.1941(16) 0.025(3) Uiso d . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C8 . . 108.28(8) y
C1 N1 C9 . . 124.37(9) y
C8 N1 C9 . . 125.74(8) y
C10 N2 C10 . 2 118.97(12) ?
C2 C1 N1 . . 110.90(9) ?
C2 C1 H1 . . 129.4(8) ?
N1 C1 H1 . . 119.7(8) ?
C1 C2 C3 . . 106.07(8) ?
C1 C2 C13 . . 125.28(9) ?
C3 C2 C13 . . 128.44(9) ?
C4 C3 C8 . . 119.05(9) ?
C4 C3 C2 . . 134.06(9) ?
C8 C3 C2 . . 106.88(8) ?
C5 C4 C3 . . 118.85(9) ?
C5 C4 H4 . . 120.7(8) ?
C3 C4 H4 . . 120.5(8) ?
C4 C5 C6 . . 121.12(10) ?
C4 C5 H5 . . 120.9(8) ?
C6 C5 H5 . . 118.0(8) ?
C7 C6 C5 . . 121.27(10) ?
C7 C6 H6 . . 118.6(9) ?
C5 C6 H6 . . 120.1(9) ?
C6 C7 C8 . . 117.60(9) ?
C6 C7 H7 . . 121.0(8) ?
C8 C7 H7 . . 121.4(8) ?
N1 C8 C7 . . 130.04(9) ?
N1 C8 C3 . . 107.83(8) ?
C7 C8 C3 . . 122.11(9) ?
N1 C9 C10 . . 112.34(8) ?
N1 C9 H9B . . 107.8(7) ?
C10 C9 H9B . . 108.0(7) ?
N1 C9 H9A . . 109.2(7) ?
C10 C9 H9A . . 110.6(7) ?
H9B C9 H9A . . 108.9(10) ?
N2 C10 C11 . . 122.69(9) y
N2 C10 C9 . . 115.81(9) y
C11 C10 C9 . . 121.49(8) ?
C12 C11 C10 . . 117.82(9) ?
C12 C11 H11 . . 121.7(8) ?
C10 C11 H11 . . 120.5(8) ?
C11 C12 C11 2 . 120.01(13) ?
C11 C12 H12 2 . 120.00(6) ?
C11 C12 H12 . . 120.00(6) ?
C13 C13 C2 2 . 123.73(5) y
C13 C13 H13 2 . 119.5(7) ?
C2 C13 H13 . . 116.7(7) ?
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 . 1.3748(13) y
N1 C8 . 1.3773(12) y
N1 C9 . 1.4494(12) y
N2 C10 . 1.3366(11) y
N2 C10 2 1.3366(11) y
C1 C2 . 1.3698(14) y
C1 H1 . 0.979(14) ?
C2 C3 . 1.4383(13) y
C2 C13 . 1.4711(13) ?
C3 C4 . 1.4037(14) y
C3 C8 . 1.4197(13) y
C4 C5 . 1.3858(15) y
C4 H4 . 0.992(14) ?
C5 C6 . 1.4098(15) y
C5 H5 . 0.993(14) ?
C6 C7 . 1.3827(15) y
C6 H6 . 0.988(15) ?
C7 C8 . 1.3963(14) y
C7 H7 . 0.965(14) ?
C9 C10 . 1.5221(13) ?
C9 H9B . 1.000(13) ?
C9 H9A . 0.993(12) ?
C10 C11 . 1.3939(13) ?
C11 C12 . 1.3906(12) ?
C11 H11 . 0.967(13) ?
C12 C11 2 1.3906(12) ?
C12 H12 . 0.97(2) ?
C13 C13 2 1.340(2) y
C13 H13 . 1.005(13) ?
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
C9 H9B Cg1 5_555 1.000(13) 2.804(15) 3.7233(11) 153.0(10)
C9 H9B Cg1 6_555 1.000(13) 2.804(15) 3.7233(11) 153.0(10)
C11 H11 Cg2 6_555 0.967(13) 2.728(13) 3.6732(11) 166.0(10)
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_4
_geom_torsion
C8 N1 C1 C2 . . -1.46(11)
C9 N1 C1 C2 . . -167.67(8)
N1 C1 C2 C3 . . 0.31(11)
N1 C1 C2 C13 . . 175.40(9)
C1 C2 C3 C4 . . 179.80(10)
C13 C2 C3 C4 . . 4.93(18)
C1 C2 C3 C8 . . 0.91(10)
C13 C2 C3 C8 . . -173.97(9)
C8 C3 C4 C5 . . -0.68(14)
C2 C3 C4 C5 . . -179.47(10)
C3 C4 C5 C6 . . 0.45(15)
C4 C5 C6 C7 . . 0.04(15)
C5 C6 C7 C8 . . -0.29(15)
C1 N1 C8 C7 . . -179.47(9)
C9 N1 C8 C7 . . -13.50(16)
C1 N1 C8 C3 . . 2.00(10)
C9 N1 C8 C3 . . 167.97(8)
C6 C7 C8 N1 . . -178.31(9)
C6 C7 C8 C3 . . 0.05(14)
C4 C3 C8 N1 . . 179.12(8)
C2 C3 C8 N1 . . -1.79(10)
C4 C3 C8 C7 . . 0.44(14)
C2 C3 C8 C7 . . 179.53(8)
C1 N1 C9 C10 . . 78.48(12)
C8 N1 C9 C10 . . -85.33(11)
C10 N2 C10 C11 2 . -0.33(7)
C10 N2 C10 C9 2 . -178.83(9)
N1 C9 C10 N2 . . -25.39(11)
N1 C9 C10 C11 . . 156.09(9)
N2 C10 C11 C12 . . 0.63(13)
C9 C10 C11 C12 . . 179.05(7)
C10 C11 C12 C11 . 2 -0.30(6)
C1 C2 C13 C13 . 2 -48.0(2)
C3 C2 C13 C13 . 2 125.99(15)
