Biomimetic macrocycle-forming Diels-Alder reaction of an iminium dienophile: synthetic studies directed toward gymnodimine.
Johannes, Jeffrey W.; Wenglowsky, Steve; Kishi, Yoshito; Organic letters 7 (2005) 3997–4000; doi:10.1021/ol051553n

data_1506691
_publ_section_title
;
 Biomimetic macrocycle-forming Diels-Alder reaction of an iminium
 dienophile: synthetic studies directed toward gymnodimine.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              3997
_journal_page_last               4000
_journal_paper_doi               10.1021/ol051553n
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C35 H48 Br N O4'
_chemical_formula_weight         626.65
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.470(2)
_cell_length_b                   17.247(4)
_cell_length_c                   17.307(4)
_cell_measurement_reflns_used    934
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      24.22
_cell_measurement_theta_min      2.56
_cell_volume                     3125.2(12)
_computing_cell_refinement       'SMART (BRUKER, V5.625, 2001)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.22, 2001)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 2000, V6.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       '\w, 0.3 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22114
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.354
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.834556
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     562
_refine_ls_number_reflns         7466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0095P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0775
_reflns_number_gt                6061
_reflns_number_total             7466
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051553nsi20050701_020600.cif
_cod_data_source_block           yk40t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1506691