Controlling Diaza-Cope Rearrangement Reactions with Resonance-Assisted Hydrogen Bonds
Jik Chin; Fabrizio Mancin; Nirusha Thavarajah; Donghyung Lee; Alan Lough; Doo Soo Chung; Journal of the American Chemical Society 125 (2003) 15276–15277; doi:10.1021/ja0387554

data_4114505
_publ_section_title
;
 Controlling Diaza-Cope Rearrangement Reactions with Resonance-Assisted
 Hydrogen Bonds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15276
_journal_page_last               15277
_journal_paper_doi               10.1021/ja0387554
_journal_volume                  125
_journal_year                    2003
_chemical_formula_moiety         'C30 H28 N2 O4, C H Cl3, C H4 O'
_chemical_formula_sum            'C32 H33 Cl3 N2 O5'
_chemical_formula_weight         631.95
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                108.690(2)
_cell_angle_beta                 101.930(2)
_cell_angle_gamma                95.511(2)
_cell_formula_units_Z            1
_cell_length_a                   6.7660(3)
_cell_length_b                   10.2215(4)
_cell_length_c                   11.6018(6)
_cell_measurement_reflns_used    13687
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.6
_cell_volume                     732.15(6)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'SHELXTL V6.12'
_computing_publication_material  'SHELXTL V6.12'
_computing_structure_refinement  'SHELXTL V6.12(Sheldrick, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f scans and \w scans with \k offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0954
_diffrn_reflns_av_sigmaI/netI    0.0999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9007
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.358
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
?
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       plate
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       0.13(3)
_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   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0852
_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^)+(0.1325P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2136
_refine_ls_wR_factor_ref         0.2328
_reflns_number_gt                1681
_reflns_number_total             2557
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja0387554si20030929_024325.cif
_cod_data_source_block           k02164
_cod_database_code               4114505