#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:20:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180073 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/19/7051915.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_7051915
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             2007-12-30T18:36:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.957(3)
_cell_length_b                   22.606(6)
_cell_length_c                   6.2052(16)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.25
_cell_measurement_theta_min      3.1
_cell_volume                     1354.0(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1487
_diffrn_reflns_av_unetI/netI     0.1016
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10773
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         1.8
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.1428
_refine_ls_R_factor_gt           0.063
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0768P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.143
_refine_ls_wR_factor_ref         0.1845
_reflns_number_gt                930
_reflns_number_total             1942
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b800050f.txt
_cod_data_source_block           4
_cod_database_code               7051915
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
C2 C 0.1074(5) -0.4839(2) 0.2912(9) 0.0688(15) Uani 1 1 d . A 1
H2 H 0.0351 -0.4651 0.1912 0.083 Uiso 1 1 calc R A 1
C3 C 0.1483(6) -0.4621(2) 0.5097(9) 0.0733(15) Uani 0.87 1 d P A 1
H3 H 0.0998 -0.4314 0.5559 0.088 Uiso 0.87 1 calc PR A 1
C4 C 0.2571(6) -0.4861(2) 0.6484(9) 0.0746(16) Uani 1 1 d . A 1
H4 H 0.2861 -0.4717 0.7928 0.09 Uiso 1 1 calc R A 1
C5 C 0.4577(6) -0.5534(3) 0.7068(9) 0.0714(16) Uani 1 1 d . A 1
H5 H 0.4908 -0.5397 0.8515 0.086 Uiso 1 1 calc R A 1
C6 C 0.5336(5) -0.5924(2) 0.6223(9) 0.0703(16) Uani 1 1 d . A 1
H6 H 0.6221 -0.6027 0.7031 0.084 Uiso 1 1 calc R A 1
C7 C 0.5649(5) -0.6552(2) 0.3134(10) 0.0713(16) Uani 1 1 d . A 1
H7 H 0.6545 -0.6641 0.3935 0.086 Uiso 1 1 calc R A 1
C8 C 0.5163(6) -0.6772(2) 0.1073(10) 0.0693(15) Uani 1 1 d . A 1
H8 H 0.5766 -0.6974 0.0402 0.083 Uiso 1 1 calc R A 1
C9 C 0.3259(6) -0.6971(2) -0.2198(9) 0.0708(15) Uani 1 1 d . A 1
H9 H 0.3889 -0.7148 -0.2884 0.085 Uiso 1 1 calc R A 1
C10 C 0.1934(6) -0.6982(2) -0.3250(8) 0.0656(15) Uani 1 1 d . A 1
H10 H 0.1655 -0.7123 -0.4699 0.079 Uiso 1 1 calc R A 1
C11 C -0.0469(7) -0.6878(2) -0.2935(9) 0.0707(16) Uani 1 1 d . A 1
H11 H -0.0748 -0.7036 -0.436 0.085 Uiso 1 1 calc R A 1
C13 C -0.0973(5) -0.6541(2) 0.0191(8) 0.0620(14) Uani 1 1 d . A 1
H13 H -0.1615 -0.6472 0.1027 0.074 Uiso 1 1 calc R A 1
C14 C 0.0366(5) -0.63982(17) 0.1129(7) 0.0535(12) Uani 0.87 1 d P A 1
H14 H 0.0607 -0.6238 0.2553 0.064 Uiso 0.87 1 calc PR A 1
C15 C 0.2758(5) -0.5557(2) 0.3628(7) 0.0489(12) Uani 1 1 d . A 1
C16 C 0.3295(5) -0.5332(2) 0.5795(8) 0.0560(13) Uani 1 1 d . A 1
C17 C 0.3446(4) -0.60563(19) 0.2868(7) 0.0471(12) Uani 1 1 d . A 1
C18 C 0.4781(5) -0.6178(2) 0.4094(8) 0.0550(13) Uani 1 1 d . A 1
C19 C 0.2835(5) -0.63935(18) 0.0885(7) 0.0476(12) Uani 1 1 d . A 1
C20 C 0.3780(5) -0.67059(19) -0.0084(8) 0.0568(13) Uani 1 1 d . A 1
C21 C 0.1394(5) -0.64908(17) -0.0042(7) 0.0501(12) Uani 1 1 d . A 1
C22 C 0.0934(5) -0.67708(18) -0.2117(8) 0.0547(13) Uani 1 1 d . A 1
C1 C 0.1676(4) -0.53041(17) 0.2205(6) 0.0550(11) Uani 0.13 1 d P A 1
H1 H 0.1353 -0.5448 0.0767 0.066 Uiso 0.13 1 calc PR A 1
C12 C -0.1455(5) -0.67767(18) -0.1869(8) 0.0741(14) Uani 0.13 1 d P A 1
H12 H -0.2386 -0.6859 -0.2477 0.089 Uiso 0.13 1 calc PR A 1
N1 N 0.1676(4) -0.53041(17) 0.2205(6) 0.0550(11) Uani 0.87 1 d P B 2
N12 N -0.1455(5) -0.67767(18) -0.1869(8) 0.0741(14) Uani 0.87 1 d P C 2
N3 N 0.1483(6) -0.4621(2) 0.5097(9) 0.0733(15) Uani 0.13 1 d P D 2
N14 N 0.0366(5) -0.63982(17) 0.1129(7) 0.0535(12) Uani 0.13 1 d P E 2
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
C1 C2 C3 123.1(5) . . ?
C4 C3 C2 118.8(5) . . ?
C3 C4 C16 120.7(5) . . ?
C6 C5 C16 120.9(5) . . ?
C5 C6 C18 119.9(5) . . ?
C8 C7 C18 119.9(5) . . ?
C7 C8 C20 121.8(5) . . ?
C10 C9 C20 123.9(5) . . ?
C9 C10 C22 118.8(5) . . ?
C12 C11 C22 126.0(5) . . ?
C14 C13 C12 125.5(5) . . ?
C13 C14 C21 120.4(5) . . ?
C1 C15 C16 121.8(4) . . ?
C1 C15 C17 118.8(4) . . ?
C16 C15 C17 119.2(4) . . ?
C5 C16 C4 122.5(5) . . ?
C5 C16 C15 119.9(5) . . ?
C4 C16 C15 117.2(5) . . ?
C18 C17 C19 120.5(4) . . ?
C18 C17 C15 116.0(4) . . ?
C19 C17 C15 123.4(4) . . ?
C17 C18 C6 122.1(5) . . ?
C17 C18 C7 118.8(5) . . ?
C6 C18 C7 119.0(5) . . ?
C20 C19 C21 117.2(4) . . ?
C20 C19 C17 115.9(4) . . ?
C21 C19 C17 126.5(4) . . ?
C8 C20 C9 121.3(5) . . ?
C8 C20 C19 120.5(5) . . ?
C9 C20 C19 118.1(5) . . ?
C22 C21 C14 115.1(5) . . ?
C22 C21 C19 120.5(5) . . ?
C14 C21 C19 123.8(4) . . ?
C11 C22 C21 119.1(5) . . ?
C11 C22 C10 121.4(5) . . ?
C21 C22 C10 119.3(5) . . ?
C2 C1 C15 118.1(4) . . ?
C11 C12 C13 113.7(5) . . ?
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
C2 C1 1.337(6) . ?
C2 C3 1.406(6) . ?
C3 C4 1.322(6) . ?
C4 C16 1.411(6) . ?
C5 C6 1.349(7) . ?
C5 C16 1.402(6) . ?
C6 C18 1.421(6) . ?
C7 C8 1.347(6) . ?
C7 C18 1.439(6) . ?
C8 C20 1.397(6) . ?
C9 C10 1.321(6) . ?
C9 C20 1.419(6) . ?
C10 C22 1.434(6) . ?
C11 C12 1.331(6) . ?
C11 C22 1.386(6) . ?
C13 C14 1.356(6) . ?
C13 C12 1.359(5) . ?
C14 C21 1.408(6) . ?
C15 C1 1.342(5) . ?
C15 C16 1.414(6) . ?
C15 C17 1.457(6) . ?
C17 C18 1.388(5) . ?
C17 C19 1.448(5) . ?
C19 C20 1.422(6) . ?
C19 C21 1.426(6) . ?
C21 C22 1.407(6) . ?
