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_4106315
_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         'C15 H15 N3 O2'
_chemical_formula_sum            'C15 H15 N3 O2'
_chemical_formula_weight         269.30
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.309(2)
_cell_angle_beta                 89.473(2)
_cell_angle_gamma                85.920(2)
_cell_formula_units_Z            4
_cell_length_a                   5.2162(2)
_cell_length_b                   15.3273(4)
_cell_length_c                   16.7226(5)
_cell_measurement_reflns_used    7326
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.30
_cell_measurement_theta_min      2.89
_cell_volume                     1332.09(7)
_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 0.968
_diffrn_measured_fraction_theta_max 0.968
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23115
_diffrn_reflns_theta_full        67.85
_diffrn_reflns_theta_max         67.85
_diffrn_reflns_theta_min         2.65
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.9359
_exptl_absorpt_correction_T_min  0.6878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0550P)^2^+0.4838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1231
_reflns_number_gt                3516
_reflns_number_total             4679
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja200699v_si_002.cif
_cod_data_source_block           ia309_0m
_cod_database_code               4106315