#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/53/4025395.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_4025395
loop_
_publ_author_name
'Jan Storch'
'Jan Čermák'
'Jindřich Karban'
'Ivana Císařová'
'Jan Sýkora'
_publ_section_title
;
 Synthesis of 2-Aza[6]helicene and Attempts To Synthesize
 2,14-Diaza[6]helicene Utilizing Metal-Catalyzed Cycloisomerization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3137
_journal_page_last               3140
_journal_paper_doi               10.1021/jo100252a
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C26 H18 N2'
_chemical_formula_sum            'C26 H18 N2'
_chemical_formula_weight         358.44
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             10-02-08
_audit_creation_method           CRYSTALS_ver_12.82
_cell_angle_alpha                109.3100(10)
_cell_angle_beta                 110.1600(10)
_cell_angle_gamma                95.9220(10)
_cell_formula_units_Z            2
_cell_length_a                   10.0297(2)
_cell_length_b                   10.3403(2)
_cell_length_c                   10.7915(2)
_cell_measurement_reflns_used    4386
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      1
_cell_volume                     961.27(3)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT. Nonius (1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.007
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8727
_diffrn_reflns_theta_full        27.483
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.153
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1126
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.000277
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.811 0.704 0.417 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0578
_refine_ls_wR_factor_gt          0.0458
_refine_ls_wR_factor_ref         0.0458
_reflns_limit_h_max              11
_reflns_limit_h_min              -13
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3397
_reflns_number_total             4395
_reflns_threshold_expression     I>1.96u(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          1.293(2)
_cod_data_source_file            jo100252a_si_002.cif
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4025395
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N2 N 0.18310(13) 0.28185(10) 0.15164(11) 0.0436 1.0000 Uani . . . . . .
N21 N 0.31197(12) 0.80416(11) 0.72470(11) 0.0420 1.0000 Uani . . . . . .
C1 C 0.32311(15) 0.33702(12) 0.23269(12) 0.0393 1.0000 Uani . . . . . .
C3 C 0.09894(14) 0.37372(12) 0.12712(13) 0.0385 1.0000 Uani . . . . . .
C4 C 0.15151(12) 0.51752(11) 0.18345(11) 0.0311 1.0000 Uani . . . . . .
C5 C 0.36846(11) 0.72647(10) 0.33516(10) 0.0271 1.0000 Uani . . . . . .
C6 C 0.51725(12) 0.77293(12) 0.41523(12) 0.0338 1.0000 Uani . . . . . .
C7 C 0.60555(13) 0.67846(14) 0.43731(13) 0.0394 1.0000 Uani . . . . . .
C8 C 0.54488(13) 0.53635(14) 0.37845(12) 0.0383 1.0000 Uani . . . . . .
C9 C 0.39229(12) 0.48370(11) 0.29461(11) 0.0313 1.0000 Uani . . . . . .
C10 C 0.30248(11) 0.57770(10) 0.27129(10) 0.0265 1.0000 Uani . . . . . .
C11 C 0.27448(11) 0.82558(10) 0.30967(10) 0.0271 1.0000 Uani . . . . . .
C12 C 0.27868(12) 0.88694(10) 0.21140(11) 0.0307 1.0000 Uani . . . . . .
C13 C 0.18326(14) 0.97188(11) 0.17883(12) 0.0376 1.0000 Uani . . . . . .
C14 C 0.08458(15) 0.99603(12) 0.24212(14) 0.0410 1.0000 Uani . . . . . .
C15 C 0.08167(13) 0.93826(11) 0.34057(13) 0.0361 1.0000 Uani . . . . . .
C16 C 0.17670(11) 0.85385(10) 0.37605(11) 0.0288 1.0000 Uani . . . . . .
C17 C 0.17649(11) 0.80092(10) 0.48895(11) 0.0289 1.0000 Uani . . . . . .
C18 C 0.05065(11) 0.71542(11) 0.47735(11) 0.0298 1.0000 Uani . . . . . .
C19 C 0.05865(13) 0.68036(12) 0.59400(12) 0.0351 1.0000 Uani . . . . . .
C20 C 0.18928(14) 0.72666(12) 0.71314(13) 0.0391 1.0000 Uani . . . . . .
C22 C 0.30245(13) 0.84042(12) 0.61431(12) 0.0363 1.0000 Uani . . . . . .
C23 C 0.38272(13) 0.86577(11) 0.14709(11) 0.0336 1.0000 Uani . . . . . .
C24 C 0.47404(13) 0.85911(11) 0.09916(12) 0.0363 1.0000 Uani . . . . . .
C25 C 0.58763(17) 0.85461(16) 0.04387(17) 0.0469 1.0000 Uani . . . . . .
C26 C -0.08058(12) 0.66035(11) 0.34823(12) 0.0331 1.0000 Uani . . . . . .
C27 C -0.18794(12) 0.60729(12) 0.23913(13) 0.0370 1.0000 Uani . . . . . .
C28 C -0.32067(16) 0.54255(16) 0.10743(16) 0.0496 1.0000 Uani . . . . . .
H11 H 0.3874(17) 0.2727(17) 0.2532(16) 0.051(4) 1.0000 Uiso . . . . . .
H31 H -0.0076(17) 0.3299(16) 0.0646(16) 0.050(4) 1.0000 Uiso . . . . . .
H41 H 0.0840(15) 0.5790(15) 0.1633(14) 0.040(3) 1.0000 Uiso . . . . . .
H61 H 0.5634(15) 0.8748(16) 0.4588(15) 0.044(4) 1.0000 Uiso . . . . . .
H71 H 0.7129(17) 0.7160(15) 0.4963(16) 0.047(4) 1.0000 Uiso . . . . . .
H81 H 0.6084(16) 0.4696(16) 0.3933(16) 0.050(4) 1.0000 Uiso . . . . . .
H131 H 0.1862(15) 1.0160(15) 0.1090(15) 0.043(4) 1.0000 Uiso . . . . . .
H141 H 0.0163(16) 1.0566(17) 0.2214(16) 0.052(4) 1.0000 Uiso . . . . . .
H151 H 0.0122(15) 0.9568(15) 0.3882(15) 0.042(4) 1.0000 Uiso . . . . . .
H191 H -0.0286(16) 0.6232(16) 0.5916(15) 0.046(4) 1.0000 Uiso . . . . . .
H201 H 0.1978(16) 0.7018(15) 0.7961(16) 0.045(4) 1.0000 Uiso . . . . . .
H221 H 0.3943(16) 0.9015(15) 0.6256(15) 0.043(4) 1.0000 Uiso . . . . . .
H251 H 0.678(2) 0.857(2) 0.115(2) 0.081(6) 1.0000 Uiso . . . . . .
H252 H 0.563(2) 0.767(3) -0.039(2) 0.092(6) 1.0000 Uiso . . . . . .
H253 H 0.601(2) 0.932(2) 0.014(2) 0.096(7) 1.0000 Uiso . . . . . .
H281 H -0.308(2) 0.569(2) 0.030(2) 0.088(6) 1.0000 Uiso . . . . . .
H282 H -0.402(2) 0.582(2) 0.124(2) 0.093(7) 1.0000 Uiso . . . . . .
H283 H -0.342(2) 0.442(3) 0.078(2) 0.097(7) 1.0000 Uiso . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . N2 . C3 . 116.72(10) yes
C20 . N21 . C22 . 116.62(10) yes
N2 . C1 . C9 . 124.87(11) yes
N2 . C1 . H11 . 118.6(9) no
C9 . C1 . H11 . 116.5(9) no
N2 . C3 . C4 . 124.10(12) yes
N2 . C3 . H31 . 115.7(9) no
C4 . C3 . H31 . 120.1(9) no
C3 . C4 . C10 . 119.42(10) yes
C3 . C4 . H41 . 120.2(8) no
C10 . C4 . H41 . 120.4(8) no
C6 . C5 . C10 . 118.87(10) yes
C6 . C5 . C11 . 122.10(9) yes
C10 . C5 . C11 . 119.01(9) yes
C5 . C6 . C7 . 121.76(10) yes
C5 . C6 . H61 . 119.3(8) no
C7 . C6 . H61 . 118.9(8) no
C6 . C7 . C8 . 120.39(11) yes
C6 . C7 . H71 . 119.5(8) no
C8 . C7 . H71 . 120.1(8) no
C7 . C8 . C9 . 119.80(10) yes
C7 . C8 . H81 . 120.0(9) no
C9 . C8 . H81 . 120.2(9) no
C1 . C9 . C8 . 122.14(10) yes
C1 . C9 . C10 . 117.55(10) yes
C8 . C9 . C10 . 120.30(10) yes
C5 . C10 . C9 . 118.87(10) yes
C5 . C10 . C4 . 123.85(9) yes
C9 . C10 . C4 . 117.27(9) yes
C5 . C11 . C12 . 119.45(9) yes
C5 . C11 . C16 . 121.21(9) yes
C12 . C11 . C16 . 119.27(9) yes
C11 . C12 . C13 . 119.89(10) yes
C11 . C12 . C23 . 120.60(10) yes
C13 . C12 . C23 . 119.50(9) yes
C12 . C13 . C14 . 120.33(10) yes
C12 . C13 . H131 . 120.1(8) no
C14 . C13 . H131 . 119.6(8) no
C13 . C14 . C15 . 120.08(11) yes
C13 . C14 . H141 . 121.8(9) no
C15 . C14 . H141 . 118.1(9) no
C14 . C15 . C16 . 120.80(11) yes
C14 . C15 . H151 . 120.6(8) no
C16 . C15 . H151 . 118.6(8) no
C11 . C16 . C15 . 119.59(9) yes
C11 . C16 . C17 . 121.20(9) yes
C15 . C16 . C17 . 119.15(9) yes
C16 . C17 . C18 . 122.45(9) yes
C16 . C17 . C22 . 120.14(9) yes
C18 . C17 . C22 . 117.36(10) yes
C17 . C18 . C19 . 118.04(10) yes
C17 . C18 . C26 . 121.42(9) yes
C19 . C18 . C26 . 120.48(10) yes
C18 . C19 . C20 . 119.33(10) yes
C18 . C19 . H191 . 120.6(8) no
C20 . C19 . H191 . 120.1(8) no
C19 . C20 . N21 . 123.69(11) yes
C19 . C20 . H201 . 120.6(8) no
N21 . C20 . H201 . 115.7(8) no
C17 . C22 . N21 . 124.89(11) yes
C17 . C22 . H221 . 119.2(8) no
N21 . C22 . H221 . 115.9(8) no
C12 . C23 . C24 . 174.94(11) yes
C23 . C24 . C25 . 178.47(13) yes
C24 . C25 . H251 . 110.0(12) no
C24 . C25 . H252 . 111.1(12) no
H251 . C25 . H252 . 106.8(17) no
C24 . C25 . H253 . 111.7(13) no
H251 . C25 . H253 . 110.0(17) no
H252 . C25 . H253 . 107.0(18) no
C18 . C26 . C27 . 176.31(12) yes
C26 . C27 . C28 . 178.94(13) yes
C27 . C28 . H281 . 110.1(12) no
C27 . C28 . H282 . 109.3(13) no
H281 . C28 . H282 . 105.9(17) no
C27 . C28 . H283 . 109.8(14) no
H281 . C28 . H283 . 109.9(18) no
H282 . C28 . H283 . 111.7(18) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N2 . C1 . 1.3117(18) yes
N2 . C3 . 1.3648(16) yes
N21 . C20 . 1.3403(16) yes
N21 . C22 . 1.3392(15) yes
C1 . C9 . 1.4218(16) yes
C1 . H11 . 0.997(16) no
C3 . C4 . 1.3703(15) yes
C3 . H31 . 1.002(16) no
C4 . C10 . 1.4159(15) yes
C4 . H41 . 0.994(14) no
C5 . C6 . 1.3759(15) yes
C5 . C10 . 1.4330(14) yes
C5 . C11 . 1.4905(14) yes
C6 . C7 . 1.4080(17) yes
C6 . H61 . 0.983(15) no
C7 . C8 . 1.3655(18) yes
C7 . H71 . 0.996(15) no
C8 . C9 . 1.4160(17) yes
C8 . H81 . 1.001(15) no
C9 . C10 . 1.4163(14) yes
C11 . C12 . 1.4139(14) yes
C11 . C16 . 1.4019(15) yes
C12 . C13 . 1.3988(16) yes
C12 . C23 . 1.4367(15) yes
C13 . C14 . 1.3829(18) yes
C13 . H131 . 1.008(14) no
C14 . C15 . 1.3870(16) yes
C14 . H141 . 0.994(16) no
C15 . C16 . 1.3993(15) yes
C15 . H151 . 0.998(14) no
C16 . C17 . 1.4921(14) yes
C17 . C18 . 1.4064(14) yes
C17 . C22 . 1.3939(15) yes
C18 . C19 . 1.4003(15) yes
C18 . C26 . 1.4334(15) yes
C19 . C20 . 1.3788(17) yes
C19 . H191 . 0.991(15) no
C20 . H201 . 0.989(15) no
C22 . H221 . 1.006(14) no
C23 . C24 . 1.1947(16) yes
C24 . C25 . 1.4551(18) yes
C25 . H251 . 0.96(2) no
C25 . H252 . 0.97(2) no
C25 . H253 . 0.97(2) no
C26 . C27 . 1.1932(16) yes
C27 . C28 . 1.4570(17) yes
C28 . H281 . 1.00(2) no
C28 . H282 . 0.99(2) no
C28 . H283 . 0.95(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659188
2 PubChem 46217666
