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_7153804
_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_absolute_configuration ad
_chemical_formula_moiety         'C24 H19 N O'
_chemical_formula_sum            'C24 H19 N O'
_chemical_formula_weight         337.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                90
_cell_angle_beta                 103.305(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9504(14)
_cell_length_b                   11.2305(10)
_cell_length_c                   9.1731(9)
_cell_measurement_reflns_used    1941
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.4560
_cell_measurement_theta_min      4.7770
_cell_volume                     1699.3(3)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 5.2031
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details
;
  1 omega  -49.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651   38.0000   90.0000 78

  2 omega -123.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -99.0000  150.0000 44

  3 omega   67.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651 -126.0000 -136.0000 32

  4 omega  -47.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   45.0000   30.0000 60

  5 omega   91.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.9963   45.0000 -120.0000 60

  6 omega   45.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.9963  -95.0000 -180.0000 56

  7 omega   34.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.9963 -125.0000  150.0000 76

  8 omega   25.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.9963  -95.0000  -90.0000 67

  9 omega   33.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.9963  -30.0000  120.0000 58

 10 omega   54.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.9963  -30.0000   60.0000 36
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0124028000
_diffrn_orient_matrix_UB_12      -0.1350092000
_diffrn_orient_matrix_UB_13      -0.0277236000
_diffrn_orient_matrix_UB_21      -0.0923260000
_diffrn_orient_matrix_UB_22      0.0160847000
_diffrn_orient_matrix_UB_23      -0.0250595000
_diffrn_orient_matrix_UB_31      -0.0062854000
_diffrn_orient_matrix_UB_32      0.0190304000
_diffrn_orient_matrix_UB_33      -0.1684134000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2772
_diffrn_reflns_point_group_measured_fraction_full 0.555
_diffrn_reflns_point_group_measured_fraction_max 0.530
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.663
_diffrn_reflns_theta_min         4.764
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79481
_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    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 191 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         1846
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.049
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0739P)^2^+2.3398P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1464
_reflns_Friedel_coverage         0.130
_reflns_Friedel_fraction_full    0.132
_reflns_Friedel_fraction_max     0.122
_reflns_number_gt                1756
_reflns_number_total             1846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob00411f3.cif
_cod_data_source_block           xstr0016
_cod_database_code               7153804
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C23 H17 N1 O1'
_chemical_oxdiff_usercomment     'Frank King MW323'
_reflns_odcompleteness_completeness 97.94
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_shelx_res_checksum              10276
_shelx_hkl_checksum              7693