Organocatalytic [4+2] addition reactions via tetraenamine intermediate
Stiller, Julian; Poulsen, Pernille H.; Cruz, David Cruz; Dourado, Jorge; Davis, Rebecca L.; Jørgensen, Karl Anker; Chemical Science 5 (2014) 2052–; doi:10.1039/c4sc00081a

data_1514300
_publ_section_title
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 Organocatalytic [4+2] addition reactions via tetraenamine intermediate
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_journal_issue                   5
_journal_name_full               'Chemical Science'
_journal_page_first              2052
_journal_paper_doi               10.1039/c4sc00081a
_journal_volume                  5
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 Br N O4'
_chemical_formula_sum            'C21 H20 Br N O4'
_chemical_formula_weight         430.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-24
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.731(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.3326(5)
_cell_length_b                   6.3617(3)
_cell_length_c                   14.1521(7)
_cell_measurement_reflns_used    7641
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.71
_cell_measurement_theta_min      2.29
_cell_volume                     923.85(8)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13541
_diffrn_reflns_theta_full        22.69
_diffrn_reflns_theta_max         22.69
_diffrn_reflns_theta_min         1.57
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.213
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6979
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1354 before and 0.0428 after correction.
The Ratio of minimum to maximum transmission is 0.6979.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.012(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         5045
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0332P)^2^+0.6820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0774
_reflns_number_gt                4709
_reflns_number_total             5045
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc00081a2.cif
_cod_data_source_block           2013_06_24full_0m
_cod_database_code               1514300
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C15(H15), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), N5(H5), C11(H11), C12(H12), C16(H16), C20(H20), C2(H2), C14(H14),
 C7(H7A)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O7(H7)
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