Enol-Enamine Tautomerism in Crystals of 1,3-Bis(pyridin-2-yl) Propan-2-one: A Combined Crystallographic and Quantum-Chemical Investigation of the Effect of Packing on Tautomerization Processes
Oded Godsi; Boaz Turner; Kinga Suwinska; Uri Peskin; Yoav Eichen; Journal of the American Chemical Society 126 (2004) 13519–13525; doi:10.1021/ja046311h

data_4113049
_publ_section_title
;
 Enol-Enamine Tautomerism in Crystals of 1,3-Bis(pyridin-2-yl)
 Propan-2-one: A Combined Crystallographic and Quantum-Chemical
 Investigation of the Effect of Packing on Tautomerization Processes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13519
_journal_page_last               13525
_journal_paper_doi               10.1021/ja046311h
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C13 H12 N2 O'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.1582(2)
_cell_length_b                   10.6203(2)
_cell_length_c                   17.8002(3)
_cell_measurement_reflns_used    3229
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      2.910
_cell_volume                     2109.38(7)
_computing_cell_refinement
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_data_collection
'Collect data collection software (Nonius B.V., 1998)'
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Johnson & Burnet, 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean
;
1242 (horizontal) x 1152 (vertical) pixels, CCD pixel size is 22.5 x 22.5 \mm
which gives at the input a pixel of 110 x 110 \mm (with 2 x 2 binning)
;
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method
;
179 frames via \f rotation and 110 frames via \o rotation   
(rotation angle 1\%) and 2*60 s per frame   
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19542
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown-red
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0051(15)
_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   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0472P)^2^+0.3798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                2266
_reflns_number_total             2951
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja046311hsi20040622_115652.cif
_cod_data_source_block           en100
_cod_original_cell_volume        2109.39(7)
_cod_database_code               4113049