First Synthesis of Naphthalene Annulated Oxepins
Koenig, Burkhard; Dobelmann, Lars; Parham, Amir; Buchholz, Herwig; Buesing, Arne; RSC Adv.  (2014) –; doi:10.1039/C4RA10652K

data_7218700
_publ_section_title
;
 First Synthesis of Naphthalene Annulated Oxepins
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA10652K
_journal_year                    2014
_chemical_formula_moiety         'C44 H28 O'
_chemical_formula_sum            'C44 H28 O'
_chemical_formula_weight         572.66
_chemical_name_common            AMP011/230
_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_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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             2012-08-23
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.09.07 svn.r1971, GUI svn.r3853)
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
SHELXL-97, enCifer 1.4
;
_cell_angle_alpha                112.582(7)
_cell_angle_beta                 103.862(5)
_cell_angle_gamma                95.539(5)
_cell_formula_units_Z            2
_cell_length_a                   10.9104(5)
_cell_length_b                   11.7223(10)
_cell_length_c                   12.8808(9)
_cell_measurement_reflns_used    16825
_cell_measurement_temperature    200
_cell_measurement_theta_max      73.8577
_cell_measurement_theta_min      4.2619
_cell_volume                     1443.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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
;
SHELXD, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      200
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 10.3876
_diffrn_detector_type            'Atlas CCD'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega   -2.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   94.0000   12.0000 25

  2 omega  -97.00   -2.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.8658  125.0000 -150.0000 95

  3 omega  -98.00  -51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.8658  -38.0000  -30.0000 47

  4 omega  -49.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.8658  -38.0000  -30.0000 34

  5 omega   12.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.8658   57.0000   60.0000 103

  6 omega  -32.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.8658  -57.0000   30.0000 102

  7 omega   18.00   52.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.8658   57.0000 -180.0000 34

  8 omega   80.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.8658   57.0000 -180.0000 26

  9 omega    7.00   32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   81.0000 -134.0000 25

 10 omega   19.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   82.0000 -176.0000 25

 11 omega   19.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   82.0000  116.0000 25

 12 omega   19.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   82.0000  -11.0000 25

 13 omega   21.00   46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000  -60.0000 25

 14 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   80.0000   40.0000 25

 15 omega   19.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000   90.0000 25

 16 omega   25.00   53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000  -91.0000 28

 17 omega   71.00  100.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  113.0000 29

 18 omega   27.00   53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  113.0000 26

 19 omega   29.00   61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000 -140.0000 32

 20 omega   33.00   61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000  134.0000 28

 21 omega   32.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  173.0000 75

 22 omega  -89.00  -39.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000  -75.0000  -94.0000 50

 23 omega -149.00 -104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -69.0000   46.0000 45

 24 omega  -69.00  -42.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -69.0000   46.0000 27

 25 omega  -66.00  -40.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -77.0000   -5.0000 26

 26 omega -146.00  -89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -77.0000   -5.0000 57

 27 omega  -78.00  -41.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -75.0000  -33.0000 37

 28 omega  -76.00  -45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -78.0000  -73.0000 -169.0000 31

 29 omega -149.00 -106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -78.0000  -73.0000 -169.0000 43

 30 omega  -75.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -120.0000 26

 31 omega  -76.00  -50.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -76.0000 -168.0000 26

 32 omega  -79.00  -53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -68.0000   89.0000 26

 33 omega  -77.00  -51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   50.0000 26

 34 omega  -76.00  -50.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -76.0000   21.0000 26

 35 omega  -78.00  -52.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -69.0000 -149.0000 26

 36 omega  -78.00  -52.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -66.0000  -92.0000 26

 37 omega  -76.00  -50.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -30.0000 26

 38 omega  -75.00  -50.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -72.0000  -62.0000 25

 39 omega  -77.00  -51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -180.0000 26

 40 omega  -75.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  150.0000 26

 41 omega  -77.00  -50.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  120.0000 27

 42 omega  -76.00  -50.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -90.0000 26

 43 omega  -77.00  -51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -70.0000   66.0000 26

 44 omega   25.00   57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707  -94.0000  -30.0000 32

 45 omega   81.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   61.0000 -150.0000 27

 46 omega   41.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707  -45.0000  -30.0000 35

 47 omega   23.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707  -94.0000  120.0000 85

 48 omega  120.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707  126.0000  -69.0000 35

 49 omega   24.00   61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707  -94.0000 -120.0000 37

 50 omega   73.00  142.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   77.0000    0.0000 69

 51 omega   45.00  134.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707  -77.0000  -90.0000 89

 52 omega   73.00  153.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   77.0000  -60.0000 80

 53 omega   73.00  143.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   77.0000 -120.0000 70

 54 omega   74.00  144.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   77.0000   90.0000 70

 55 omega   42.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707  -45.0000   90.0000 25

 56 omega  116.00  157.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   77.0000   60.0000 41

 57 omega   78.00  113.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   77.0000   60.0000 35

 58 omega   75.00  150.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   77.0000  120.0000 75

 59 omega  109.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   77.0000 -180.0000 49

 60 omega   74.00  149.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   77.0000   30.0000 75

 61 omega   73.00  156.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   77.0000  150.0000 83

 62 omega   73.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   77.0000 -180.0000 32

 63 omega   33.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707 -125.0000  120.0000 78

 64 omega   36.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707 -126.0000 -110.0000 66

 65 omega   73.00  152.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   77.0000  -30.0000 79

 66 omega   77.00  138.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   61.0000 -120.0000 61

 67 omega   74.00  150.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707   77.0000  -90.0000 76

 68 omega   37.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707 -125.0000  -60.0000 84

 69 omega   78.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707  -94.0000    0.0000 26

 70 omega  123.00  154.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707  125.0000 -180.0000 31

 71 omega   29.00   54.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707  -94.0000    0.0000 25

 72 omega   85.00  120.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0707  125.0000 -180.0000 35
;
_diffrn_measurement_device       'kappa four circle diffractometer'
_diffrn_measurement_device_type  'Agilent Technologies SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0068629000
_diffrn_orient_matrix_UB_12      0.1063160000
_diffrn_orient_matrix_UB_13      -0.0419364000
_diffrn_orient_matrix_UB_21      -0.0347791000
_diffrn_orient_matrix_UB_22      -0.0982283000
_diffrn_orient_matrix_UB_23      -0.1287468000
_diffrn_orient_matrix_UB_31      -0.1443430000
_diffrn_orient_matrix_UB_32      -0.0127278000
_diffrn_orient_matrix_UB_33      -0.0089307000
_diffrn_radiation_collimation    'focussing mirrors'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27946
_diffrn_reflns_theta_full        74.36
_diffrn_reflns_theta_max         74.36
_diffrn_reflns_theta_min         4.27
_diffrn_source                   'microfocus source'
_diffrn_source_current           0.8
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent NOVA microfocus source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_id                exp_1062
_exptl_crystal_size_max          0.4212
_exptl_crystal_size_mid          0.2811
_exptl_crystal_size_min          0.1181
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0104(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.426
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         5788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.426
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0438
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1644
_reflns_number_gt                5394
_reflns_number_total             5788
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra10652k2.cif
_cod_data_source_block           exp_1062
_cod_original_cell_volume        1443.76(17)
_cod_database_code               7218700
_chemical_oxdiff_formula         'C44 H28 O1'
_chemical_oxdiff_usercomment     AMP011/230
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97