#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:20:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180073 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/19/7051911.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7051911
loop_
_publ_author_name
'Bazzini, Cristina'
'Caronna, Tullio'
'Fontana, Francesca'
'Macchi, Piero'
'Mele, Andrea'
'Natali Sora, Isabella'
'Panzeri, Walter'
'Sironi, Angelo'
_publ_section_title
;
 Synthesis, crystal structure and crystal packing of diaza[5]helicenes
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1710
_journal_paper_doi               10.1039/b800050f
_journal_volume                  32
_journal_year                    2008
_chemical_formula_sum            'C20 H12 N2'
_chemical_formula_weight         280.32
_chemical_name_systematic
;
?
;
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2007-12-29T18:04:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.000
_cell_angle_beta                 107.010(2)
_cell_angle_gamma                90.000
_cell_formula_units_Z            8
_cell_length_a                   18.4176(19)
_cell_length_b                   13.8286(14)
_cell_length_c                   11.2744(12)
_cell_measurement_reflns_used    5344
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.3
_cell_volume                     2745.9(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30420
_diffrn_reflns_theta_full        31.98
_diffrn_reflns_theta_max         31.98
_diffrn_reflns_theta_min         1.16
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         8931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.3348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1489
_reflns_number_gt                4781
_reflns_number_total             8931
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b800050f.txt
_cod_data_source_block           2-I
_cod_database_code               7051911
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.10720(9) -0.82945(11) 0.48243(15) 0.0499(4) Uani 1 1 d . . .
C2 C -0.13422(10) -0.91634(14) 0.42884(18) 0.0619(4) Uani 1 1 d . . .
C3 C -0.17335(10) -0.92091(17) 0.30254(19) 0.0684(5) Uani 1 1 d . . .
C4 C -0.18830(10) -0.83840(17) 0.23476(18) 0.0683(5) Uani 1 1 d . . .
C16 C -0.16535(9) -0.74728(14) 0.28916(15) 0.0578(4) Uani 1 1 d . . .
C15 C -0.11944(8) -0.74286(11) 0.41413(14) 0.0477(3) Uani 1 1 d . . .
C6 C -0.17995(10) -0.58340(19) 0.2768(2) 0.0765(6) Uani 1 1 d . . .
C18 C -0.13468(9) -0.56870(13) 0.40213(18) 0.0611(5) Uani 1 1 d . . .
C17 C -0.09521(8) -0.64835(11) 0.46787(15) 0.0485(4) Uani 1 1 d . . .
C7 C -0.13013(11) -0.47652(14) 0.4592(2) 0.0724(6) Uani 1 1 d . . .
C8 C -0.08878(11) -0.46436(13) 0.5783(2) 0.0704(5) Uani 1 1 d . . .
C20 C -0.04088(9) -0.53931(11) 0.64148(17) 0.0563(4) Uani 1 1 d . . .
C19 C -0.03816(8) -0.62897(10) 0.58381(14) 0.0448(3) Uani 1 1 d . . .
C9 C 0.00762(11) -0.52514(14) 0.76525(19) 0.0652(5) Uani 1 1 d . . .
C22 C 0.07488(9) -0.66116(11) 0.76029(14) 0.0482(3) Uani 1 1 d . . .
C21 C 0.02775(8) -0.68845(10) 0.64146(13) 0.0413(3) Uani 1 1 d . . .
C11 C 0.14284(9) -0.71118(13) 0.81531(15) 0.0540(4) Uani 1 1 d . . .
C12 C 0.16645(9) -0.78318(12) 0.75320(15) 0.0528(4) Uani 1 1 d . . .
C13 C 0.12267(9) -0.80788(11) 0.63406(15) 0.0477(3) Uani 1 1 d . . .
C14 C 0.05485(8) -0.76229(10) 0.57973(14) 0.0433(3) Uani 1 1 d . . .
C101 C -0.55076(8) -0.24072(10) 0.02688(13) 0.0422(3) Uani 1 1 d . . .
C102 C -0.61727(9) -0.19199(11) 0.01522(15) 0.0478(3) Uani 1 1 d . . .
C103 C -0.66262(9) -0.21505(13) 0.09085(15) 0.0546(4) Uani 1 1 d . . .
C104 C -0.64155(9) -0.28773(13) 0.17481(16) 0.0551(4) Uani 1 1 d . . .
C116 C -0.57454(9) -0.34017(11) 0.18688(13) 0.0472(3) Uani 1 1 d . . .
C115 C -0.52603(8) -0.31536(10) 0.11457(12) 0.0402(3) Uani 1 1 d . . .
C106 C -0.50994(11) -0.47828(13) 0.25800(16) 0.0615(5) Uani 1 1 d . . .
C118 C -0.45960(9) -0.46558(11) 0.18305(14) 0.0506(4) Uani 1 1 d . . .
C117 C -0.46057(8) -0.37670(10) 0.12258(12) 0.0416(3) Uani 1 1 d . . .
C107 C -0.41163(10) -0.54184(12) 0.16997(17) 0.0604(5) Uani 1 1 d . . .
C108 C -0.36792(10) -0.53230(12) 0.09363(18) 0.0610(5) Uani 1 1 d . . .
C120 C -0.36212(8) -0.44080(11) 0.03942(15) 0.0512(4) Uani 1 1 d . . .
C119 C -0.40199(8) -0.35999(10) 0.06344(13) 0.0423(3) Uani 1 1 d . . .
C109 C -0.31563(9) -0.42941(15) -0.04091(18) 0.0619(5) Uani 1 1 d . . .
C122 C -0.33050(8) -0.26510(12) -0.04855(14) 0.0507(4) Uani 1 1 d . . .
C121 C -0.37674(8) -0.26687(10) 0.03158(13) 0.0427(3) Uani 1 1 d . . .
C111 C -0.30682(10) -0.17554(14) -0.08400(17) 0.0612(5) Uani 1 1 d . . .
C112 C -0.32245(10) -0.09189(15) -0.03425(18) 0.0637(5) Uani 1 1 d . . .
C113 C -0.36185(9) -0.09297(12) 0.05476(18) 0.0572(4) Uani 1 1 d . . .
C114 C -0.38897(8) -0.17875(10) 0.08596(15) 0.0475(3) Uani 1 1 d . . .
N5 N -0.19271(8) -0.66564(15) 0.21915(15) 0.0755(5) Uani 1 1 d . . .
N10 N 0.06069(9) -0.58213(11) 0.82536(14) 0.0634(4) Uani 1 1 d . . .
N105 N -0.56244(8) -0.41930(11) 0.26550(13) 0.0602(4) Uani 1 1 d . . .
N110 N -0.30309(8) -0.34826(12) -0.08951(14) 0.0631(4) Uani 1 1 d . . .
H1 H -0.0820(9) -0.8260(10) 0.5699(15) 0.048(4) Uiso 1 1 d . . .
H2 H -0.1246(12) -0.9796(16) 0.479(2) 0.096(7) Uiso 1 1 d . . .
H3 H -0.1931(12) -0.9824(16) 0.265(2) 0.088(7) Uiso 1 1 d . . .
H4 H -0.2156(12) -0.8391(13) 0.152(2) 0.075(6) Uiso 1 1 d . . .
H6 H -0.2009(11) -0.5248(15) 0.2340(19) 0.084(6) Uiso 1 1 d . . .
H7 H -0.1590(11) -0.4292(15) 0.4051(19) 0.085(6) Uiso 1 1 d . . .
H8 H -0.0841(12) -0.4024(16) 0.6262(19) 0.088(6) Uiso 1 1 d . . .
H9 H -0.0013(10) -0.4664(14) 0.8056(18) 0.077(6) Uiso 1 1 d . . .
H11 H 0.1718(10) -0.6908(12) 0.8979(17) 0.059(5) Uiso 1 1 d . . .
H12 H 0.2137(12) -0.8153(13) 0.7926(18) 0.074(6) Uiso 1 1 d . . .
H13 H 0.1399(9) -0.8570(11) 0.5877(15) 0.055(4) Uiso 1 1 d . . .
H14 H 0.0272(9) -0.7786(11) 0.4990(15) 0.049(4) Uiso 1 1 d . . .
H101 H -0.5208(9) -0.2271(10) -0.0294(15) 0.049(4) Uiso 1 1 d . . .
H102 H -0.6316(9) -0.1407(11) -0.0484(16) 0.054(4) Uiso 1 1 d . . .
H103 H -0.7089(11) -0.1788(12) 0.0853(16) 0.061(5) Uiso 1 1 d . . .
H104 H -0.6716(12) -0.3072(14) 0.2288(19) 0.080(6) Uiso 1 1 d . . .
H106 H -0.5012(10) -0.5336(13) 0.3084(18) 0.071(5) Uiso 1 1 d . . .
H107 H -0.4133(10) -0.6018(13) 0.2130(16) 0.065(5) Uiso 1 1 d . . .
H108 H -0.3364(10) -0.5807(13) 0.0743(17) 0.066(5) Uiso 1 1 d . . .
H109 H -0.2941(11) -0.4861(14) -0.0642(18) 0.077(6) Uiso 1 1 d . . .
H111 H -0.2753(12) -0.1776(13) -0.1446(19) 0.081(6) Uiso 1 1 d . . .
H112 H -0.3077(10) -0.0309(13) -0.0546(17) 0.071(6) Uiso 1 1 d . . .
H113 H -0.3722(10) -0.0318(13) 0.0968(17) 0.067(5) Uiso 1 1 d . . .
H114 H -0.4151(9) -0.1808(10) 0.1494(14) 0.046(4) Uiso 1 1 d . . .
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 0 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C15 121.71(16) . . ?
C1 C2 C3 120.10(19) . . ?
C4 C3 C2 119.71(19) . . ?
C3 C4 C16 121.39(17) . . ?
N5 C16 C4 117.86(17) . . ?
N5 C16 C15 122.91(17) . . ?
C4 C16 C15 119.12(16) . . ?
C1 C15 C16 117.48(15) . . ?
C1 C15 C17 123.82(14) . . ?
C16 C15 C17 118.31(14) . . ?
N5 C6 C18 126.00(18) . . ?
C17 C18 C7 120.78(18) . . ?
C17 C18 C6 118.15(18) . . ?
C7 C18 C6 121.07(17) . . ?
C18 C17 C19 117.35(15) . . ?
C18 C17 C15 115.85(15) . . ?
C19 C17 C15 126.71(13) . . ?
C8 C7 C18 120.37(17) . . ?
C7 C8 C20 119.94(19) . . ?
C19 C20 C8 121.02(18) . . ?
C19 C20 C9 118.29(15) . . ?
C8 C20 C9 120.68(17) . . ?
C20 C19 C17 117.86(14) . . ?
C20 C19 C21 115.47(14) . . ?
C17 C19 C21 126.29(13) . . ?
N10 C9 C20 126.26(16) . . ?
N10 C22 C11 115.90(14) . . ?
N10 C22 C21 123.58(14) . . ?
C11 C22 C21 120.40(14) . . ?
C14 C21 C22 116.93(13) . . ?
C14 C21 C19 124.09(13) . . ?
C22 C21 C19 118.19(13) . . ?
C12 C11 C22 120.71(15) . . ?
C11 C12 C13 119.63(15) . . ?
C14 C13 C12 120.83(15) . . ?
C13 C14 C21 121.38(14) . . ?
C102 C101 C115 121.58(14) . . ?
C101 C102 C103 120.50(15) . . ?
C104 C103 C102 119.74(15) . . ?
C103 C104 C116 120.94(15) . . ?
N105 C116 C104 116.28(14) . . ?
N105 C116 C115 123.32(14) . . ?
C104 C116 C115 120.26(14) . . ?
C101 C115 C116 116.89(13) . . ?
C101 C115 C117 124.21(13) . . ?
C116 C115 C117 118.27(13) . . ?
N105 C106 C118 126.02(15) . . ?
C117 C118 C107 121.56(16) . . ?
C117 C118 C106 118.31(15) . . ?
C107 C118 C106 120.12(15) . . ?
C118 C117 C119 117.37(13) . . ?
C118 C117 C115 115.68(13) . . ?
C119 C117 C115 126.57(12) . . ?
C108 C107 C118 120.23(16) . . ?
C107 C108 C120 119.73(16) . . ?
C119 C120 C108 120.99(16) . . ?
C119 C120 C109 118.63(15) . . ?
C108 C120 C109 120.38(16) . . ?
C120 C119 C117 117.70(13) . . ?
C120 C119 C121 115.76(14) . . ?
C117 C119 C121 126.45(13) . . ?
N110 C109 C120 125.28(16) . . ?
N110 C122 C111 117.44(16) . . ?
N110 C122 C121 123.02(15) . . ?
C111 C122 C121 119.44(15) . . ?
C114 C121 C122 117.77(14) . . ?
C114 C121 C119 123.76(14) . . ?
C122 C121 C119 118.13(13) . . ?
C112 C111 C122 120.85(17) . . ?
C111 C112 C113 120.39(17) . . ?
C114 C113 C112 119.79(17) . . ?
C113 C114 C121 121.24(16) . . ?
C6 N5 C16 116.55(17) . . ?
C9 N10 C22 115.97(15) . . ?
C106 N105 C116 116.24(14) . . ?
C109 N110 C122 116.65(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.371(2) . ?
C1 C15 1.406(2) . ?
C2 C3 1.397(3) . ?
C3 C4 1.356(3) . ?
C4 C16 1.411(3) . ?
C16 N5 1.385(2) . ?
C16 C15 1.417(2) . ?
C15 C17 1.455(2) . ?
C6 N5 1.297(3) . ?
C6 C18 1.430(3) . ?
C18 C17 1.406(2) . ?
C18 C7 1.420(3) . ?
C17 C19 1.443(2) . ?
C7 C8 1.346(3) . ?
C8 C20 1.411(2) . ?
C20 C19 1.408(2) . ?
C20 C9 1.433(3) . ?
C19 C21 1.453(2) . ?
C9 N10 1.284(2) . ?
C22 N10 1.383(2) . ?
C22 C11 1.406(2) . ?
C22 C21 1.418(2) . ?
C21 C14 1.407(2) . ?
C11 C12 1.360(2) . ?
C12 C13 1.392(2) . ?
C13 C14 1.373(2) . ?
C101 C102 1.370(2) . ?
C101 C115 1.4096(19) . ?
C102 C103 1.394(2) . ?
C103 C104 1.357(3) . ?
C104 C116 1.403(2) . ?
C116 N105 1.385(2) . ?
C116 C115 1.417(2) . ?
C115 C117 1.455(2) . ?
C106 N105 1.287(2) . ?
C106 C118 1.436(3) . ?
C118 C117 1.403(2) . ?
C118 C107 1.411(2) . ?
C117 C119 1.443(2) . ?
C107 C108 1.346(3) . ?
C108 C120 1.423(2) . ?
C120 C119 1.406(2) . ?
C120 C109 1.425(3) . ?
C119 C121 1.450(2) . ?
C109 N110 1.299(2) . ?
C122 N110 1.388(2) . ?
C122 C111 1.409(2) . ?
C122 C121 1.411(2) . ?
C121 C114 1.412(2) . ?
C111 C112 1.353(3) . ?
C112 C113 1.400(3) . ?
C113 C114 1.372(2) . ?
