#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2003030.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_2003030
loop_
_publ_author_name
'Kiralj, Rudolf'
'Koji\'c-Prodi\'c, Biserka'
'Piantanida, Ivo'
'\<Zini\'c, Mladen'
_publ_section_title
;
 Crystal and molecular structures of diazapyrenes and a study of
 \p&#x00B7;&#x00B7;&#x00B7;\p interactions
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              55
_journal_page_last               69
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C16 H12 N2'
_chemical_formula_weight         232.286
_chemical_name_systematic
;
5,10-dimethyl-4,9-diazapyrene
;
_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'
_cell_angle_alpha                90
_cell_angle_beta                 101.230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.0246(5)
_cell_length_b                   15.5147(5)
_cell_length_c                   9.1453(9)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    295(3)
_cell_measurement_theta_max      42
_cell_measurement_theta_min      11
_cell_volume                     560.10(9)
_computing_cell_refinement
'CAD4 (Enraf Nonius 1988) software <CELDIM> routine'
_computing_data_collection       'EXPRESS-CAD4 (Enraf Nonius 1992) software'
_computing_data_reduction        'HELENA (Spek, 1994)'
_computing_molecular_graphics
;
PLATON93 (Spek, 1982, 1990) & ORTEP (Johnson, 1965), PLUTON93 (Spek 1991)
;
_computing_publication_material  'PLATON93 (Spek 1982, 1990)'
_computing_structure_refinement  'SHELX76 (Sheldrick, 1976)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985, 1990)'
_diffrn_ambient_temperature      295(3)
_diffrn_measurement_device       'Enraf-Nonius CAD4 diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focused sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  .0360
_diffrn_reflns_av_sigmaI/netI    .0946
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1297
_diffrn_reflns_reduction_process
;
 ?
;
_diffrn_reflns_theta_max         74.19
_diffrn_reflns_theta_min         5.70
_diffrn_standards_interval_count 41
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .60
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       needle
_exptl_crystal_F_000             244
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .04
_exptl_crystal_size_min          .04
_refine_diff_density_max         .138
_refine_diff_density_min         -.147
_refine_ls_abs_structure_details
;
 ?
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   .629
_refine_ls_goodness_of_fit_obs   .660
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.238
_refine_ls_restrained_S_obs      .660
_refine_ls_R_factor_all          .2272
_refine_ls_R_factor_obs          .0425
_refine_ls_shift/esd_max         -.031
_refine_ls_shift/esd_mean        .006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.1673P)^2^+0.5865P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         .4272
_refine_ls_wR_factor_obs         .1281
_reflns_number_observed          425
_reflns_number_total             1135
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    na0085.cif
_[local]_cod_data_source_block   DIAZA1
_cod_original_cell_volume        560.10(10)
_cod_database_code               2003030
loop_
_symmetry_equiv_pos_as_xyz
X,Y,Z
X,1/2-Y,1/2+Z
-X,-Y,-Z
-X,1/2+Y,1/2-Z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N4 .050(2) .0373(18) .055(2) .0011(17) .0137(17) .0012(17)
C1 .050(3) .045(3) .056(3) -.002(2) .013(2) .000(2)
C2 .058(3) .056(3) .046(2) .001(2) .008(2) .003(2)
C3 .060(3) .048(3) .051(3) .009(2) .011(2) .010(2)
C5 .051(2) .033(2) .055(3) .0051(18) .017(2) .0039(19)
C11 .044(2) .035(2) .043(2) .0039(17) .0174(18) .0000(17)
C31 .046(2) .042(2) .048(2) .001(2) .0163(18) .002(2)
C51 .048(2) .037(2) .049(2) .0013(18) .0178(19) .0022(18)
C53 .070(4) .038(3) .080(4) .002(2) .016(3) .007(3)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
N4 .1676(8) .35583(19) .1291(3) .0470(11) Uani d 1
C1 .4509(10) .6138(3) .2271(4) .0500(17) Uani d 1
C2 .5860(11) .5469(3) .3198(4) .0536(16) Uani d 1
C3 .4908(11) .4623(3) .2872(4) .0530(17) Uani d 1
C5 -.0548(10) .3387(2) .0075(4) .0454(14) Uani d 1
C11 .1207(9) .5102(3) .0649(3) .0395(12) Uani d 1
C31 .2587(10) .4415(3) .1597(4) .0444(12) Uani d 1
C51 -.2135(10) .4036(2) -.0975(4) .0435(12) Uani d 1
C53 -.1415(15) .2452(3) -.0233(6) .062(2) Uani d 1
H1 .511(11) .675(3) .248(5) .067(13) Uiso d 1
H2 .756(11) .559(3) .412(5) .069(13) Uiso d 1
H3 .613(10) .421(3) .352(4) .057(13) Uiso d 1
H531 -.055(11) .226(3) -.116(5) .073(15) Uiso d 1
H532 -.394(14) .237(3) -.039(6) .103(19) Uiso d 1
H533 -.024(13) .214(3) .062(5) .089(17) 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 .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 2 2
0 2 -2
1 7 0
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
C5 N4 C31 . . 118.2(3) no
C2 C1 C51 . 3_565 119.8(4) no
C1 C2 C3 . . 121.4(4) no
C2 C3 C31 . . 121.1(4) no
N4 C5 C51 . . 124.1(3) no
N4 C5 C53 . . 116.7(3) no
C51 C5 C53 . . 119.3(4) no
C11 C11 C31 3_565 . 117.9(4) no
C31 C11 C51 . 3_565 122.0(3) no
C11 C11 C51 3_565 3_565 120.1(4) no
N4 C31 C3 . . 120.0(4) no
N4 C31 C11 . . 122.6(3) no
C3 C31 C11 . . 117.4(4) no
C1 C51 C5 3_565 . 124.6(3) no
C5 C51 C11 . 3_565 117.1(3) no
C1 C51 C11 3_565 3_565 118.3(3) no
C2 C1 H1 . . 123(3) no
C51 C1 H1 3_565 . 117(3) no
C1 C2 H2 . . 120(3) no
C3 C2 H2 . . 119(3) no
C2 C3 H3 . . 115(3) no
C31 C3 H3 . . 124(3) no
C5 C53 H531 . . 109(3) no
C5 C53 H532 . . 110(3) no
C5 C53 H533 . . 106(3) no
H531 C53 H532 . . 110(4) no
H531 C53 H533 . . 109(4) no
H532 C53 H533 . . 112(4) no
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
N4 C5 . 1.312(5) no
N4 C31 . 1.393(5) no
C1 C2 . 1.383(6) no
C1 C51 3_565 1.396(5) no
C2 C3 . 1.383(7) no
C3 C31 . 1.383(5) no
C5 C51 . 1.451(5) no
C5 C53 . 1.506(6) no
C11 C31 . 1.417(6) no
C11 C11 3_565 1.416(4) no
C11 C51 3_565 1.405(6) no
C1 H1 . .99(5) no
C2 H2 . .99(5) no
C3 H3 . .94(4) no
C53 H531 . 1.02(5) no
C53 H532 . 1.01(6) no
C53 H533 . .96(5) no
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_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C31 N4 C5 C53 . . . 178.8(4) no
C5 N4 C31 C11 . . . .0(19) no
C5 N4 C31 C3 . . . 179.6(4) no
C31 N4 C5 C51 . . . -.2(6) no
C51 C1 C2 C3 3_565 . . -.1(6) no
C2 C1 C51 C5 . 3_565 3_565 179.8(4) no
C2 C1 C51 C11 . 3_565 . -.4(6) no
C1 C2 C3 C31 . . . .6(6) no
C2 C3 C31 N4 . . . 179.8(4) no
C2 C3 C31 C11 . . . -.5(6) no
C53 C5 C51 C1 . . 3_565 1.2(6) no
C53 C5 C51 C11 . . 3_565 -179.1(4) no
N4 C5 C51 C11 . . 3_565 -.2(6) no
N4 C5 C51 C1 . . 3_565 -179.9(5) no
C51 C11 C31 N4 3_565 . . 179.7(4) no
C11 C11 C31 N4 3_565 . . .5(5) no
C11 C11 C31 C3 3_565 . . -179.1(4) no
C31 C11 C11 C31 . 3_565 3_565 -180(2) no
C51 C11 C11 C51 3_565 3_565 . -180.0(16) no
C31 C11 C51 C1 . 3_565 . .4(6) no
C31 C11 C51 C5 . 3_565 3_565 -179.8(3) no
C11 C11 C51 C1 3_565 3_565 . 179.6(4) no
C51 C11 C31 C3 3_565 . . .0(12) no
C31 C11 C11 C51 . 3_565 . -.8(5) no