Spectroscopic and X-ray Crystallographic Evidence for Electrostatic Effects in 4-Substituted Cyclohexanone-Derived Hydrazones, Imines, and Corresponding Salts
David J. Dibble; Joseph W. Ziller; K. A. Woerpel; Journal of Organic Chemistry 76 (2011) 7706–7719; doi:10.1021/jo200950s

data_4026596
_publ_section_title
;
 Spectroscopic and X-ray Crystallographic Evidence for Electrostatic
 Effects in 4-Substituted Cyclohexanone-Derived Hydrazones, Imines, and
 Corresponding Salts
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7706
_journal_page_last               7719
_journal_paper_doi               10.1021/jo200950s
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C19 H20 N4 O5'
_chemical_formula_weight         384.39
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                101.2251(10)
_cell_angle_beta                 94.5613(9)
_cell_angle_gamma                103.6311(10)
_cell_formula_units_Z            2
_cell_length_a                   5.9628(5)
_cell_length_b                   11.7329(9)
_cell_length_c                   13.0844(10)
_cell_measurement_reflns_used    4115
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      4.37
_cell_volume                     865.01(12)
_computing_cell_refinement       'Bruker SMART APEX2/SAINT'
_computing_data_collection       'Bruker SMART APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega'
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8793
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.39
_diffrn_reflns_theta_min         4.31
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0479P)^2^+0.2286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                3004
_reflns_number_total             3866
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200950s_si_002.cif
_cod_data_source_block           kaw123
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4026596