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_4037057
_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
_audit_creation_date             2016-07-18
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_cell_angle_alpha                90
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_cell_formula_units_Z            4
_cell_length_a                   11.2737(4)
_cell_length_b                   14.8446(4)
_cell_length_c                   16.9670(5)
_cell_measurement_reflns_used    8916
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8910
_cell_measurement_theta_min      3.9350
_cell_volume                     2833.38(15)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
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  1 omega  -75.00  -38.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 37

  2 omega  -73.00  -29.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
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  3 omega  -12.00   33.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
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  4 omega  -43.00   30.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000  150.0000 73

  5 omega   48.00  126.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   75.0000   13.5941 78

  6 omega   47.00   74.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -180.0000 27

  7 omega  -12.00   21.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000 -120.0000 33

  8 omega  -12.00   77.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
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  9 omega   -4.00   92.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
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 10 omega   41.00   68.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000 -120.0000 27

 11 omega   44.00   70.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -92.0000    0.0000 26

 12 omega   92.00  122.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   64.0000   30.0000 30

 13 omega   91.00  130.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000  120.0000 39

 14 omega   55.00   92.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000 -180.0000 37

 15 omega   91.00  159.00   1.0000    8.5000
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 16 omega   53.00   80.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   90.0000 27

 17 omega  101.00  144.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000  -90.0000 43

 18 omega  134.00  160.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000 -150.0000 26

 19 omega  126.00  171.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000 -120.0000 45

 20 omega   90.00  116.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000 -120.0000 26

 21 omega   54.00   82.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -60.0000 28

 22 omega   39.00   69.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  120.0000 30

 23 omega   42.00   68.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -92.0000  -30.0000 26

 24 omega   95.00  130.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -92.0000  -30.0000 35

 25 omega   95.00  132.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000  -30.0000 37

 26 omega   50.00   78.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000   30.0000 28

 27 omega   60.00  100.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  -30.0000 40

 28 omega  136.00  168.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000 -180.0000 32

 29 omega   75.00  101.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000   60.0000 26

 30 omega   46.00   84.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  150.0000 38

 31 omega  129.00  178.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000   30.0000 49

 32 omega   42.00   67.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000   90.0000 25

 33 omega   47.00   83.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -27.0000   61.7910 36

 34 omega   54.00   95.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  120.0000 41

 35 omega  146.00  172.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   60.0000 26

 36 omega   86.00  122.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000   30.0000 36

 37 omega   60.00   86.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -64.0000 -120.0000 26

 38 omega   39.00   91.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -30.0000 52

 39 omega   45.00   91.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   30.0000 46

 40 omega   91.00  117.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -64.0000  120.0000 26

 41 omega  -72.00   26.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -90.0000 98

 42 omega   -4.00   42.00   1.0000    2.1200
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    -        0.0000  -99.0000    0.0000 46

 43 omega  -69.00   21.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  150.0000 90

 44 omega -113.00  -12.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  120.0000 101

 45 omega -113.00  -12.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -180.0000 101

 46 omega -113.00  -12.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000   60.0000 101

 47 omega -113.00  -12.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -120.0000 101

 48 omega  -16.00   82.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -38.0000  -30.0000 98

 49 omega   26.00  126.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  -30.0000 100

 50 omega   26.00   76.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  -90.0000 50
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_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0446
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_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
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_diffrn_reflns_point_group_measured_fraction_full 1.000
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_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.535
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_exptl_absorpt_correction_T_min  0.26523
_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            yellow
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0755
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1167P)^2^+1.1043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2144
_refine_ls_wR_factor_ref         0.2372
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_reflns_number_gt                3719
_reflns_number_total             5192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01395_si_005.cif
_cod_data_source_block           exp_937
_cod_original_cell_volume        2833.38(16)
_cod_database_code               4037057
_chemical_oxdiff_formula         'C H N'
_reflns_odcompleteness_completeness 90.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B)
2.b Me refined with riding coordinates:
 C92(H92A,H92B,H92C)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C31(H31), C9(H9), C28(H28), C24(H24), C17(H17), C37(H37), C27(H27),
 C10(H10), C15(H15), C32(H32), C14(H14), C25(H25), C12(H12), C36(H36), C11(H11),
  C33(H33), C34(H34), C90(H90), C91(H91)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'