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_4106316
_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 H16 N3 O2, C4 H F6 O4 '
_chemical_formula_sum            'C19 H17 F6 N3 O6'
_chemical_formula_weight         497.36
_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                98.277(2)
_cell_angle_beta                 98.104(2)
_cell_angle_gamma                98.997(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0657(15)
_cell_length_b                   10.783(2)
_cell_length_c                   14.797(3)
_cell_measurement_reflns_used    4942
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      2.59
_cell_volume                     1086.4(4)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0449
_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       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11003
_diffrn_reflns_theta_full        25.32
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_min         1.94
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_correction_T_min  0.9373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       needle
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.782
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.015(10)
_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   1.313
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         3935
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.324
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0892
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3137
_refine_ls_wR_factor_ref         0.3445
_reflns_number_gt                2693
_reflns_number_total             3935
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja200699v_si_003.cif
_cod_data_source_block           ia1010
_cod_database_code               4106316