Synthesis and Structural Elucidation of Diversely Functionalized 5,10-Diaza[5]Helicenes
Deepali Waghray; Jing Zhang; Jeroen Jacobs; Wienand Nulens; Nikola Basarić; Luc Van Meervelt; Wim Dehaen; Journal of Organic Chemistry 77 (2012) 10176–10183; doi:10.1021/jo301814m

data_4027725
_publ_contact_author_name
;
;
_publ_section_title
;
 Synthesis and Structural Elucidation of Diversely Functionalized
 5,10-Diaza[5]Helicenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10176
_journal_page_last               10183
_journal_paper_doi               10.1021/jo301814m
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C22 H16 N2 O2'
_chemical_formula_sum            'C22 H16 N2 O2'
_chemical_formula_weight         340.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-02-07
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                100.64(3)
_cell_angle_beta                 107.39(3)
_cell_angle_gamma                96.14(3)
_cell_formula_units_Z            2
_cell_length_a                   7.965(3)
_cell_length_b                   8.718(3)
_cell_length_c                   12.816(5)
_cell_measurement_reflns_used    2907
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3084
_cell_measurement_theta_min      3.2539
_cell_volume                     822.1(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega   22.00   51.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   57.0000   60.0000 29

  2 omega  -20.00   24.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -99.0000 -180.0000 44

  3 omega  -86.00   -1.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -57.0000  -90.0000 85

  4 omega  -37.00   39.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   38.0000   60.0000 76

  5 omega  -47.00   34.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   77.0000  150.0000 81
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0533278000
_diffrn_orient_matrix_UB_12      0.0582861000
_diffrn_orient_matrix_UB_13      -0.0132660000
_diffrn_orient_matrix_UB_21      0.0605496000
_diffrn_orient_matrix_UB_22      0.0321110000
_diffrn_orient_matrix_UB_23      -0.0244747000
_diffrn_orient_matrix_UB_31      -0.0498332000
_diffrn_orient_matrix_UB_32      -0.0512822000
_diffrn_orient_matrix_UB_33      -0.0526489000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0131
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5069
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'SuperNova (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.5136
_exptl_crystal_size_mid          0.1932
_exptl_crystal_size_min          0.1117
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+0.1687P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                2768
_reflns_number_total             3300
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301814m_si_002.cif
_cod_data_source_block           wdh1000
_cod_original_cell_volume        822.0(5)
_cod_database_code               4027725
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 98.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32