#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/89/2208994.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_2208994
loop_
_publ_author_name
'G. Senthil Kumar'
'K. Chinnakali'
'M. Gayatri Swaroop'
'P. Rajakumar'
'Hoong-Kun Fun'
_publ_section_title
1,9-Diazahexacyclo[17.6.1.1^3,7^.1^9,16^.0^10,15^.0^20,25^]hexacosa-3,5,7(26),10(15),11,13,16(27),17,19(28),20(25),21,23-dodecaene
_journal_coeditor_code           SJ2029
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1809
_journal_page_last               o1811
_journal_paper_doi               10.1107/S1600536806010919
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C26 H20 N2'
_chemical_formula_moiety         'C26 H20 N2'
_chemical_formula_sum            'C26 H20 N2'
_chemical_formula_weight         360.44
_chemical_name_systematic
;
Dibenzo[a-4,5;a'-10,11]-3,12-diazatetracyclo[12.3.1.1^3,6^.1^9,12^]
eicosa-6(19),7,9(20),14(18),15,17-hexene
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.635(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.6434(9)
_cell_length_b                   11.2843(5)
_cell_length_c                   9.0441(3)
_cell_measurement_reflns_used    1440
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.243
_cell_measurement_theta_min      2.246
_cell_volume                     1850.32(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      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0670
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13509
_diffrn_reflns_theta_full        30.80
_diffrn_reflns_theta_max         30.80
_diffrn_reflns_theta_min         2.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.7615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.175
_refine_ls_extinction_coef       0.0035(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 1998)'
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.0514
_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)+(0.0658P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1543
_reflns_number_gt                1316
_reflns_number_total             2891
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2029.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 
;
_cod_original_cell_volume        1850.32(13)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2208994
_cod_database_fobs_code          2208994
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 0.37824(7) 0.30926(11) 0.05131(15) 0.0495(4) Uani d . 1
C C1 0.42547(9) 0.21631(14) 0.0625(2) 0.0539(4) Uani d . 1
H H1 0.4582 0.2135 0.0107 0.065 Uiso calc R 1
C C2 0.41798(9) 0.12908(14) 0.1595(2) 0.0532(4) Uani d . 1
C C3 0.36182(9) 0.16900(14) 0.21269(19) 0.0509(4) Uani d . 1
C C4 0.32884(10) 0.12107(16) 0.3115(2) 0.0634(5) Uani d . 1
H H4 0.3428 0.0468 0.3579 0.076 Uiso calc R 1
C C5 0.27535(11) 0.18558(19) 0.3390(2) 0.0713(6) Uani d . 1
H H5 0.2525 0.1537 0.4030 0.086 Uiso calc R 1
C C6 0.25482(10) 0.29821(18) 0.2723(2) 0.0686(5) Uani d . 1
H H6 0.2188 0.3401 0.2935 0.082 Uiso calc R 1
C C7 0.28656(9) 0.34807(16) 0.17651(19) 0.0572(5) Uani d . 1
H H7 0.2730 0.4233 0.1330 0.069 Uiso calc R 1
C C8 0.33969(8) 0.28272(14) 0.14635(18) 0.0473(4) Uani d . 1
C C9 0.38667(9) 0.42826(14) -0.0023(2) 0.0558(5) Uani d . 1
H H9A 0.3397 0.4692 -0.0361 0.067 Uiso calc R 1
H H9B 0.4004 0.4225 -0.0942 0.067 Uiso calc R 1
C C10 0.44456(8) 0.49999(13) 0.12796(18) 0.0472(4) Uani d . 1
C C11 0.44502(9) 0.62272(14) 0.1287(2) 0.0564(5) Uani d . 1
H H11 0.4086 0.6647 0.0483 0.068 Uiso calc R 1
C C12 0.5000 0.6822(2) 0.2500 0.0634(7) Uani d S 1
H H12 0.5000 0.7646 0.2500 0.076 Uiso calc SR 1
C C13 0.5000 0.44210(19) 0.2500 0.0508(6) Uani d S 1
H H13 0.5000 0.3597 0.2500 0.061 Uiso calc SR 1
C C14 0.46359(9) 0.02190(14) 0.2112(2) 0.0685(6) Uani d . 1
H H14 0.4398 -0.0511 0.1880 0.082 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 0.0033 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 . . 107.73(13) y
C1 N1 C9 . . 124.46(14) y
C8 N1 C9 . . 124.52(14) y
C2 C1 N1 . . 111.13(15) ?
C2 C1 H1 . . 124.4 ?
N1 C1 H1 . . 124.4 ?
C1 C2 C3 . . 106.04(14) ?
C1 C2 C14 . . 126.53(16) ?
C3 C2 C14 . . 127.17(15) ?
C4 C3 C8 . . 118.70(16) ?
C4 C3 C2 . . 134.24(16) ?
C8 C3 C2 . . 107.05(14) ?
C5 C4 C3 . . 118.95(18) ?
C5 C4 H4 . . 120.5 ?
C3 C4 H4 . . 120.5 ?
C4 C5 C6 . . 121.06(19) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C7 C6 C5 . . 121.41(18) ?
C7 C6 H6 . . 119.3 ?
C5 C6 H6 . . 119.3 ?
C6 C7 C8 . . 117.80(17) ?
C6 C7 H7 . . 121.1 ?
C8 C7 H7 . . 121.1 ?
N1 C8 C7 . . 129.92(15) ?
N1 C8 C3 . . 107.99(14) ?
C7 C8 C3 . . 122.07(15) ?
N1 C9 C10 . . 112.33(13) y
N1 C9 H9A . . 109.1 ?
C10 C9 H9A . . 109.1 ?
N1 C9 H9B . . 109.1 ?
C10 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.9 ?
C13 C10 C11 . . 117.87(16) ?
C13 C10 C9 . . 119.53(14) ?
C11 C10 C9 . . 122.59(15) ?
C12 C11 C10 . . 119.43(17) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
C11 C12 C11 . 2_655 121.9(2) ?
C11 C12 H12 . . 119.1 ?
C11 C12 H12 2_655 . 119.1 ?
C10 C13 C10 2_655 . 123.5(2) ?
C10 C13 H13 2_655 . 118.2 ?
C10 C13 H13 . . 118.2 ?
C14 C14 C2 2_655 . 124.63(9) y
C14 C14 H14 2_655 . 117.7 ?
C2 C14 H14 . . 117.7 ?
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 . 1.378(2) y
N1 C8 . 1.379(2) y
N1 C9 . 1.459(2) y
C1 C2 . 1.363(2) y
C1 H1 . 0.93 ?
C2 C3 . 1.435(2) y
C2 C14 . 1.470(2) y
C3 C4 . 1.399(2) y
C3 C8 . 1.412(2) y
C4 C5 . 1.377(2) y
C4 H4 . 0.93 ?
C5 C6 . 1.398(3) y
C5 H5 . 0.93 ?
C6 C7 . 1.368(2) y
C6 H6 . 0.93 ?
C7 C8 . 1.388(2) y
C7 H7 . 0.93 ?
C9 C10 . 1.518(2) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 C13 . 1.3805(18) ?
C10 C11 . 1.385(2) ?
C11 C12 . 1.381(2) ?
C11 H11 . 0.93 ?
C12 C11 2_655 1.381(2) ?
C12 H12 . 0.93 ?
C13 C10 2_655 1.3805(18) ?
C13 H13 . 0.93 ?
C14 C14 2_655 1.329(3) y
C14 H14 . 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
C13 H13 N1 . 0.93 2.44 2.8087(18) 103
C13 H13 N1 2_655 0.93 2.44 2.8087(18) 103
C9 H9B Cg2 5_665 0.97 2.82 3.7184(19) 154
C9 H9B Cg2 6_565 0.97 2.82 3.7184(19) 154
C13 H13 Cg1 1_555 0.93 2.62 3.2625(18) 127
C13 H13 Cg1 2_655 0.93 2.62 3.2625(18) 127
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_4
_geom_torsion
C8 N1 C1 C2 . 1.12(17)
C9 N1 C1 C2 . 161.33(14)
N1 C1 C2 C3 . 0.38(18)
N1 C1 C2 C14 . -174.05(14)
C1 C2 C3 C4 . 179.50(17)
C14 C2 C3 C4 . -6.1(3)
C1 C2 C3 C8 . -1.69(17)
C14 C2 C3 C8 . 172.69(15)
C8 C3 C4 C5 . 0.8(2)
C2 C3 C4 C5 . 179.54(16)
C3 C4 C5 C6 . -1.2(3)
C4 C5 C6 C7 . 0.5(3)
C5 C6 C7 C8 . 0.5(2)
C1 N1 C8 C7 . 179.24(15)
C9 N1 C8 C7 . 19.0(2)
C1 N1 C8 C3 . -2.17(16)
C9 N1 C8 C3 . -162.37(13)
C6 C7 C8 N1 . 177.61(14)
C6 C7 C8 C3 . -0.8(2)
C4 C3 C8 N1 . -178.58(13)
C2 C3 C8 N1 . 2.39(16)
C4 C3 C8 C7 . 0.1(2)
C2 C3 C8 C7 . -178.88(13)
C1 N1 C9 C10 . -78.79(19)
C8 N1 C9 C10 . 78.17(17)
N1 C9 C10 C13 . 24.37(19)
N1 C9 C10 C11 . -156.67(15)
C13 C10 C11 C12 . -0.2(2)
C9 C10 C11 C12 . -179.14(12)
C10 C11 C12 C11 2_655 0.09(11)
C11 C10 C13 C10 2_655 0.08(11)
C9 C10 C13 C10 2_655 179.09(15)
C1 C2 C14 C14 2_655 57.1(3)
C3 C2 C14 C14 2_655 -116.2(3)
