Total synthesis of an oxepine natural product, (±)-janoxepin.
Doveston, Richard G.; Steendam, René; Jones, Stuart; Taylor, Richard J. K.; Organic letters 14 (2012) 1122–1125; doi:10.1021/ol300039x

data_1503625
_publ_section_title
;
 Total synthesis of an oxepine natural product, (+-)-janoxepin.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1122
_journal_page_last               1125
_journal_paper_doi               10.1021/ol300039x
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C19 H23 N3 O3'
_chemical_formula_sum            'C19 H23 N3 O3'
_chemical_formula_weight         341.41
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-09-13
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.09.07 svn.r1971, GUI svn.r3853)
;
_cell_angle_alpha                97.904(4)
_cell_angle_beta                 105.810(4)
_cell_angle_gamma                112.461(4)
_cell_formula_units_Z            4
_cell_length_a                   13.0580(5)
_cell_length_b                   13.0653(5)
_cell_length_c                   14.0770(6)
_cell_measurement_reflns_used    6176
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      30.6057
_cell_measurement_theta_min      2.8356
_cell_volume                     2055.14(18)
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_details
;
  1 omega  -59.00    5.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.4240   90.0000  172.0000 64

  2 omega  -47.00   47.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8302  -77.0000 -120.0000 94

  3 omega  -40.00   -3.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8302  -77.0000  -30.0000 37

  4 omega   -7.00   86.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8302   77.0000    0.0000 93

  5 omega    3.00   93.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8302   77.0000   90.0000 90
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0220516000
_diffrn_orient_matrix_UB_12      -0.0600742000
_diffrn_orient_matrix_UB_13      -0.0209273000
_diffrn_orient_matrix_UB_21      0.0122427000
_diffrn_orient_matrix_UB_22      0.0100258000
_diffrn_orient_matrix_UB_23      -0.0448754000
_diffrn_orient_matrix_UB_31      0.0575935000
_diffrn_orient_matrix_UB_32      0.0041952000
_diffrn_orient_matrix_UB_33      0.0225997000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17882
_diffrn_reflns_theta_full        28.22
_diffrn_reflns_theta_max         30.66
_diffrn_reflns_theta_min         2.84
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75470
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.3654
_exptl_crystal_size_mid          0.1716
_exptl_crystal_size_min          0.1007
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         11009
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0686
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1085P)^2^+0.3226P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1927
_refine_ls_wR_factor_ref         0.2104
_reflns_number_gt                7619
_reflns_number_total             11009
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300039x_si_001.cif
_cod_data_source_block           rjkt1101
_cod_original_cell_volume        2055.13(18)
_cod_database_code               1503625
_chemical_oxdiff_formula         'C24 Al1 Cl3 F54 O6 P2'
_chemical_oxdiff_usercomment     'Richard's RD10/003/C1 Janoxepin'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22