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_4027724
_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         'C20 H10 Cl2 N2'
_chemical_formula_sum            'C20 H10 Cl2 N2'
_chemical_formula_weight         349.20
_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             2012-02-03
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                96.007(2)
_cell_angle_beta                 90.540(3)
_cell_angle_gamma                90.553(3)
_cell_formula_units_Z            4
_cell_length_a                   7.5929(3)
_cell_length_b                   9.3350(2)
_cell_length_c                   21.6474(7)
_cell_measurement_reflns_used    16653
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3126
_cell_measurement_theta_min      2.8298
_cell_volume                     1525.78(8)
_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, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -39.00   52.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   57.0000 -180.0000 91

  2 omega  -65.00  -36.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513 -178.0000  150.0000 29

  3 omega  -86.00   -1.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -57.0000   30.0000 85

  4 omega  -14.00   20.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -99.0000 -180.0000 34

  5 omega  -78.00    7.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -77.0000  -60.0000 85

  6 omega   12.00   64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701   38.0000  150.0000 52

  7 omega  -93.00  -35.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513 -178.0000  -60.0000 58

  8 omega  -94.00  -34.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  178.0000 -150.0000 60

  9 omega  -50.00   40.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  -57.0000   60.0000 90

 10 omega  -13.00   65.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701 -107.0000  -53.0000 78

 11 omega   -3.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701   57.0000 -150.0000 91

 12 omega  -20.00   25.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -99.0000  -90.0000 45

 13 omega  -86.00    4.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -57.0000   60.0000 90

 14 omega   -3.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701   57.0000  -30.0000 91

 15 omega  -13.00   50.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701 -107.0000  126.0000 63
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0114342000
_diffrn_orient_matrix_UB_12      -0.0089352000
_diffrn_orient_matrix_UB_13      0.0319248000
_diffrn_orient_matrix_UB_21      0.0898785000
_diffrn_orient_matrix_UB_22      0.0204960000
_diffrn_orient_matrix_UB_23      -0.0016789000
_diffrn_orient_matrix_UB_31      -0.0227731000
_diffrn_orient_matrix_UB_32      0.0730618000
_diffrn_orient_matrix_UB_33      0.0079836000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31138
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.84
_diffrn_source                   'SuperNova (Mo) x-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.428
_exptl_absorpt_correction_T_max  0.880
_exptl_absorpt_correction_T_min  0.857
_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    1.520
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         6234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+0.4371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0878
_reflns_number_gt                5476
_reflns_number_total             6234
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301814m_si_001.cif
_cod_data_source_block           wdh1002
_cod_original_cell_volume        1525.78(9)
_cod_database_code               4027724
_chemical_oxdiff_formula         'C30 N2 Cl2'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32