Asymmetric Formation of Bridged Benzoxazocines through an Organocatalytic Multicomponent Dienamine-Mediated One-Pot Cascade.
Ransborg, Lars Krogager; Overgaard, Mette; Hejmanowska, Joanna; Barfüsser, Sebastian; Jørgensen, Karl Anker; Albrecht, Lukasz; Organic letters 16 (2014) 4182–4185; doi:10.1021/ol501882x

data_1517284
_publ_section_title
;
 Asymmetric Formation of Bridged Benzoxazocines through an Organocatalytic
 Multicomponent Dienamine-Mediated One-Pot Cascade.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4182
_journal_page_last               4185
_journal_paper_doi               10.1021/ol501882x
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H17 Br N2 O3'
_chemical_formula_sum            'C22 H17 Br N2 O3'
_chemical_formula_weight         437.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.37972(12)
_cell_length_b                   14.8985(2)
_cell_length_c                   16.3419(3)
_cell_measurement_reflns_used    9812
_cell_measurement_temperature    105(7)
_cell_measurement_theta_max      28.3160
_cell_measurement_theta_min      2.4840
_cell_volume                     1796.74(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      105(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details
;
  1 omega  -73.00   60.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       18.5303  -57.0000  -30.0000 133

  2 omega  -23.00  110.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       18.5303   57.0000   90.0000 133

  3 omega  -73.00   60.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       18.5303  -57.0000  120.0000 133

  4 omega  -20.00   12.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -19.5459  -99.0000 -150.0000 32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0658678000
_diffrn_orient_matrix_UB_12      0.0291668000
_diffrn_orient_matrix_UB_13      0.0171196000
_diffrn_orient_matrix_UB_21      -0.0699474000
_diffrn_orient_matrix_UB_22      -0.0264412000
_diffrn_orient_matrix_UB_23      -0.0173738000
_diffrn_orient_matrix_UB_31      -0.0024715000
_diffrn_orient_matrix_UB_32      -0.0267698000
_diffrn_orient_matrix_UB_33      0.0359056000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15571
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.512
_diffrn_reflns_theta_min         1.850
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.315
_exptl_absorpt_correction_T_max  0.553
_exptl_absorpt_correction_T_min  0.308
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_description
;
;
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.2233
_exptl_crystal_size_mid          0.1614
_exptl_crystal_size_min          0.0931
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 1609 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0284
_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^)+(0.0261P)^2^+0.7193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0642
_refine_ls_wR_factor_ref         0.0653
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                4068
_reflns_number_total             4253
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol501882x_si_002.cif
_cod_data_source_block           exp_2257
_cod_depositor_comments          'Adding full bibliography for 1517284.cif.'
_cod_database_code               1517284
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C22 H17 N2 O3 Br'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C15(H15), C29(H29)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C17(H17), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25),
 C27(H27), C28(H28), C31(H31)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'