Tautomerism of 4-hydroxyterpyridine in the solid, solution and gas phases: an X-ray, FT-IR and NMR study
Murguly, Elisa; Norsten, Tyler B.; Branda, Neil; Journal of the Chemical Society, Perkin Transactions 2  (1999) 2789–; doi:10.1039/a904323c

data_7213109
_publ_section_title
;
 Tautomerism of 4-hydroxyterpyridine in the solid, solution and gas
 phases: an X-ray, FT-IR and NMR study
;
_journal_issue                   12
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              2789
_journal_paper_doi               10.1039/a904323c
_journal_year                    1999
_chemical_formula_sum            'C15.5 H11.5 Cl1.5 N3 O'
_chemical_formula_weight         308.95
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'manual editing of SHELXL-97 template'
_cell_angle_alpha                90.00
_cell_angle_beta                 111.328(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.0933(5)
_cell_length_b                   23.0093(8)
_cell_length_c                   10.3128(10)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      28.45
_cell_measurement_theta_min      26.57
_cell_volume                     2894.1(3)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuKa
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            4062
_diffrn_reflns_theta_max         57.49
_diffrn_reflns_theta_min         3.62
_diffrn_standards_interval_count 297
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.202
_exptl_absorpt_correction_T_max  .8289
_exptl_absorpt_correction_T_min  .5054
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       plate
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.06
_refine_diff_density_max         .405
_refine_diff_density_min         -.469
_refine_diff_density_rms         .053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.059
_refine_ls_goodness_of_fit_obs   1.114
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         3801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_restrained_S_obs      1.114
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_obs          0.0595
_refine_ls_shift/esd_max         0.004
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[s^2^(Fo^2^)+( 0.0439P)^2^+3.5258P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1415
_refine_ls_wR_factor_obs         0.1241
_reflns_number_observed          2748
_reflns_number_total             3801
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            904323csup1.cif
_cod_data_source_block           nrb9810
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w=1/[s^2^(Fo^2^)+(
0.0439P)^2^+3.5258P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'.
New tag '_refine_ls_weighting_details' was created. The value of the
new tag was set to 'w=1/[s^2^(Fo^2^)+( 0.0439P)^2^+3.5258P] where
P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_original_formula_sum        'C15.50 H11.50 Cl1.50 N3 O'
_cod_database_code               7213109