Synthesis and Photophysical Properties of Aza[n]helicenes.
Upadhyay, Gourav M.; Talele, Harish R.; Bedekar, Ashutosh V.; The Journal of organic chemistry 81 (2016) 7751–7759; doi:10.1021/acs.joc.6b01395

data_4037060
_publ_section_title
;
 Synthesis and Photophysical Properties of Aza[n]helicenes.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7751
_journal_page_last               7759
_journal_paper_doi               10.1021/acs.joc.6b01395
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C40 H29 N'
_chemical_formula_sum            'C40 H29 N'
_chemical_formula_weight         523.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-14
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:32:32, GUI svn.r4372)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.1119(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.2176(6)
_cell_length_b                   7.90971(14)
_cell_length_c                   22.4566(4)
_cell_measurement_reflns_used    12896
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.3270
_cell_measurement_theta_min      3.8190
_cell_volume                     5441.08(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
SHELXL, 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      150.00(10)
_diffrn_detector_area_resol_mean 8.0851
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details
;
  1 omega  -92.00  -47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.0714  124.0000   35.0000 45

  2 omega  -50.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.0714   38.0000 -180.0000 103

  3 omega  -49.00  -23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.0714  -57.0000 -180.0000 26

  4 omega  -97.00  -59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.0714  -57.0000 -180.0000 38

  5 omega   59.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.0714  178.0000  120.0000 41

  6 omega  -46.00    1.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      -72.5000   32.0000  -60.0000 47

  7 omega  -42.00    5.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      -72.5000   32.0000  150.0000 47

  8 omega -130.00  -42.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      -72.5000  -64.0000 -180.0000 88

  9 omega  -44.00   -1.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      -72.5000   32.0000 -180.0000 43

 10 omega -139.00 -113.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      -72.5000 -104.0000  -30.0000 26

 11 omega -110.00    4.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      -72.5000   77.0000  -30.0000 114

 12 omega -107.00  -79.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      -72.5000 -104.0000  -30.0000 28

 13 omega   33.00   59.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -       75.0357 -111.0000 -180.0000 26

 14 omega   71.00   97.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -       75.0357 -111.0000 -180.0000 26

 15 omega   17.00   68.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -       75.0357  -92.0000   30.0000 51

 16 omega   46.00   80.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -43.0000    0.0000 34

 17 omega  101.00  155.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  104.0000   30.0000 54

 18 omega   67.00   93.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -21.0000   60.0000 26

 19 omega   78.00  107.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -89.0000    0.0000 29

 20 omega   59.00   85.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000   17.0000   10.9359 26

 21 omega   60.00   85.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -54.0000   30.0000 25

 22 omega  110.00  155.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  104.0000 -180.0000 45

 23 omega   61.00  104.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -54.0000  120.0000 43

 24 omega   49.00   82.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -32.0000   90.0000 33

 25 omega  128.00  154.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  104.0000   90.0000 26

 26 omega   57.00   86.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -43.0000 -120.0000 29

 27 omega   72.00   98.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -103.0000 -146.0000 26

 28 omega   74.00  100.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000  -90.0000 26

 29 omega   46.00   89.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -43.0000  -90.0000 43

 30 omega  119.00  154.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000   65.0000  -30.0000 35

 31 omega   50.00   89.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -32.0000  -90.0000 39

 32 omega   99.00  154.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -89.0000 -120.0000 55

 33 omega   50.00   89.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -32.0000  150.0000 39

 34 omega   46.00   91.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -43.0000   30.0000 45

 35 omega   55.00  113.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000 -120.0000 58

 36 omega   53.00   78.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -32.0000  120.0000 25

 37 omega   56.00   98.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -54.0000 -150.0000 42

 38 omega   66.00  111.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000  150.0000 45

 39 omega   64.00   89.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -32.0000   30.0000 25

 40 omega  146.00  178.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  138.0000   60.0000 32

 41 omega   75.00  100.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -54.0000 -180.0000 25

 42 omega   43.00   68.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -21.0000    0.0000 25

 43 omega   67.00  107.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000    0.0000 40

 44 omega  132.00  158.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000   17.0000   10.9359 26

 45 omega  111.00  136.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000   65.0000 -120.0000 25

 46 omega   92.00  177.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000   54.0000   30.0000 85

 47 omega  124.00  178.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000   26.0000  -12.3951 54

 48 omega   56.00  118.00   1.0000    3.6200
omega____ theta____ kappa____ phi______ frames
    -      124.0000   26.0000  -12.3951 62
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0499766000
_diffrn_orient_matrix_UB_12      -0.0185731000
_diffrn_orient_matrix_UB_13      -0.0092891000
_diffrn_orient_matrix_UB_21      0.0037499000
_diffrn_orient_matrix_UB_22      -0.1858596000
_diffrn_orient_matrix_UB_23      -0.0189011000
_diffrn_orient_matrix_UB_31      0.0042479000
_diffrn_orient_matrix_UB_32      -0.0553415000
_diffrn_orient_matrix_UB_33      0.0666379000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28667
_diffrn_reflns_theta_full        75.43
_diffrn_reflns_theta_max         75.43
_diffrn_reflns_theta_min         3.99
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     741
_refine_ls_number_reflns         11204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0803
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1493P)^2^+1.6656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2116
_refine_ls_wR_factor_ref         0.2224
_reflns_number_gt                9606
_reflns_number_total             11204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b01395_si_001.cif
_cod_data_source_block           exp_608
_cod_original_cell_volume        5441.07(16)
_cod_database_code               4037060
_chemical_oxdiff_formula         'C H N'
_reflns_odcompleteness_completeness 93.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H13 of C13, H44 of C44, H16 of C16, H5 of C5, {H38A,H38B} of C38, H62 of
  C62, H37 of C37, H28 of C28, H71 of C71, H36 of C36, H65 of C65, H67 of C67,
  H33 of C33, H59 of C59, H10 of C10, H34 of C34, {H79A,H79B} of C79, H31 of
  C31, H30 of C30, H4 of C4, H57 of C57, H29 of C29, H70 of C70, H24 of C24,
  H76 of C76, H51 of C51, H73 of C73, H48 of C48, {H81A,H81B} of C81, H68 of
  C68, H75 of C75, H25 of C25, {H39A,H39B} of C39, H56 of C56, H74 of C74, H53
  of C53, H20 of C20, H54 of C54, {H80A,H80B} of C80, H49 of C49, {H40A,H40B}
  of C40, H21 of C21, H8 of C8, H19 of C19, H22 of C22, H50 of C50
 At 1.5 times of:
  {H82A,H82B,H82C} of C82, {H41A,H41B,H41C} of C41
2.a Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C79(H79A,H79B), C81(H81A,H81B), C39(H39A,H39B), C80(H80A,
 H80B), C40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C44(H44), C16(H16), C5(H5), C62(H62), C37(H37), C28(H28), C71(H71),
 C36(H36), C65(H65), C67(H67), C33(H33), C59(H59), C10(H10), C34(H34), C31(H31),
  C30(H30), C4(H4), C57(H57), C29(H29), C70(H70), C24(H24), C76(H76), C51(H51),
 C73(H73), C48(H48), C68(H68), C75(H75), C25(H25), C56(H56), C74(H74), C53(H53),
  C20(H20), C54(H54), C21(H21), C8(H8), C19(H19), C49(H49), C22(H22), C50(H50)
2.c Idealised Me refined as rotating group:
 C82(H82A,H82B,H82C), C41(H41A,H41B,H41C)
;