Cyclisation reactions of N-cinnamoyl-9-aminoanthracenes.
King, Frank D.; Aliev, Abil; Caddick, Stephen; Tocher, Derek; Organic & biomolecular chemistry 12 (2014) 3211–3221; doi:10.1039/c4ob00411f

data_7153805
_publ_section_title
;
 Cyclisation reactions of N-cinnamoyl-9-aminoanthracenes.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3211
_journal_page_last               3221
_journal_paper_doi               10.1039/c4ob00411f
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C25 H21 N O, 1.67(C2.1)'
_chemical_formula_sum            'C28.5 H21 N O'
_chemical_formula_weight         393.46
_chemical_name_systematic
;
 ?
;
_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
_audit_creation_date             2014-01-31
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                93.732(3)
_cell_angle_beta                 95.624(3)
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_cell_formula_units_Z            2
_cell_length_a                   8.9866(3)
_cell_length_b                   9.1620(3)
_cell_length_c                   13.9462(5)
_cell_measurement_reflns_used    10379
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.8870
_cell_measurement_theta_min      5.3830
_cell_volume                     1021.01(7)
_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)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
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_diffrn_measurement_details
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  1 omega -112.00  -58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -84.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega  -50.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000   90.0000 42

  4 omega  -36.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  -60.0000 28

  5 omega  -95.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega -115.00  -89.00   1.0000    1.0000
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  7 omega  -81.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega -111.00  -86.00   1.0000    1.0000
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  9 omega  -52.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -57.0000   60.0000 40

 10 omega   29.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651 -125.0000 -180.0000 45

 11 omega    2.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 12 omega -139.00  -74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 13 omega  -55.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 14 omega -139.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 15 omega  -53.00  -28.00   1.0000    1.0000
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 16 omega  -59.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 17 omega -135.00  -74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 18 omega  -62.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega  -54.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 20 omega -129.00 -104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 21 omega  -63.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 22 omega  -58.00  -29.00   1.0000    1.0000
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 23 omega  -53.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   90.0000 25

 24 omega -138.00 -103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 25 omega  -56.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 26 omega -124.00  -98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 27 omega -138.00 -101.00   1.0000    1.0000
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 28 omega   81.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000  120.0000 64

 29 omega   79.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000  150.0000 73

 30 omega   75.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000 -120.0000 26

 31 omega  110.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713  125.0000  -30.0000 61

 32 omega   34.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713  -45.0000  -90.0000 63

 33 omega   75.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000   60.0000 26

 34 omega   79.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000 -120.0000 77

 35 omega   75.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  -90.0000 70

 36 omega   78.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000   60.0000 98

 37 omega   78.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000 -150.0000 26

 38 omega   75.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000 -150.0000 52

 39 omega   27.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713  -95.0000  150.0000 83

 40 omega  108.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  -30.0000 27

 41 omega   25.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713  -95.0000  -90.0000 84

 42 omega   76.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  -30.0000 28

 43 omega   76.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  -60.0000 101

 44 omega   76.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000    0.0000 87

 45 omega   78.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000  -30.0000 27

 46 omega   75.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  120.0000 26

 47 omega   78.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000   90.0000 27

 48 omega   76.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  150.0000 26

 49 omega   79.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000  -90.0000 25

 50 omega   77.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 51 omega  126.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 52 omega   75.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000   30.0000 25

 53 omega   26.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 54 omega   34.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713  -45.0000   30.0000 50

 55 omega   75.00  165.00   1.0000    1.0000
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 56 omega   76.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   72.0000  -67.8892 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_12      -0.1797133000
_diffrn_orient_matrix_UB_13      -0.0451474000
_diffrn_orient_matrix_UB_21      0.1560552000
_diffrn_orient_matrix_UB_22      -0.0135607000
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_diffrn_orient_matrix_UB_31      -0.0823599000
_diffrn_orient_matrix_UB_32      -0.0541897000
_diffrn_orient_matrix_UB_33      0.0915877000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15767
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.144
_diffrn_reflns_theta_min         5.404
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72989
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       plate
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0857P)^2^+0.7310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1632
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3665
_reflns_number_total             4025
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob00411f3.cif
_cod_data_source_block           xstr0122
_cod_original_cell_volume        1021.00(7)
_cod_original_formula_sum        'C28.50 H21 N O'
_cod_database_code               7153805
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C28.5 H24 N1 O1'
_chemical_oxdiff_usercomment     'FK 15/54'
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Others
 Fixed Sof: C31(0.6) C32(0.6) C33(0.6) C34(0.3) C41(0.4) C42(0.4) C43(0.4)
 C44(0.2)
3.a Ternary CH refined with riding coordinates:
 C11(H11), C18(H18), C19(H19)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_shelx_res_checksum              8146
_shelx_hkl_checksum              77156