Isomerization Mechanism in Hydrazone-Based Rotary Switches: Lateral Shift, Rotation, or Tautomerization?
Shainaz M. Landge; Ekatarina Tkatchouk; Diego Benítez; Don Antoine Lanfranchi; Mourad Elhabiri; William A. Goddard; Ivan Aprahamian; Journal of the American Chemical Society 133 (2011) 9812–9823; doi:10.1021/ja200699v

data_4106317
_publ_contact_author             'Ivan Aprahamian'
_publ_contact_author_email       ivan.aprahamian@dartmouth.edu
_publ_section_title
;
 Isomerization Mechanism in Hydrazone-Based Rotary Switches: Lateral
 Shift, Rotation, or Tautomerization?
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9812
_journal_page_last               9823
_journal_paper_doi               10.1021/ja200699v
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C19 H18 N3 O2, C2 O2 F3'
_chemical_formula_sum            'C21 H18 F3 N3 O4'
_chemical_formula_weight         433.38
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.1330(10)
_cell_angle_beta                 83.3570(10)
_cell_angle_gamma                66.9750(10)
_cell_formula_units_Z            2
_cell_length_a                   7.6924(6)
_cell_length_b                   8.5035(6)
_cell_length_c                   16.6802(12)
_cell_measurement_reflns_used    8185
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.60
_cell_volume                     997.13(13)
_computing_cell_refinement       'APEX2 (BRUKER, V2008.5-0, 2006)'
_computing_data_collection       'COSMO (BRUKER, V1.58, 2006)'
_computing_data_reduction        'SAINT (BRUKER, V7.34A, 2006)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_publication_material
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_refinement
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution
'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w,and/f 0.5 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16260
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         2.46
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_correction_T_min  0.9554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         3654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0814P)^2^+0.2558P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1630
_reflns_number_gt                3054
_reflns_number_total             3654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja200699v_si_004.cif
_cod_data_source_block           ia910_0m
_cod_database_code               4106317