X-Ray crystallographic and spectroscopic properties of eight Schiff bases as evidence of the proton transfer reaction. Role of the intermolecular hydrogen bond
Domínguez, Oscar; Rodríguez-Molina, Braulio; Rodríguez, Mario; Ariza, Armando; Farfán, Norberto; Santillan, Rosa; New Journal of Chemistry 35 (2011) 156–; doi:10.1039/c0nj00179a

data_7052536
_publ_section_title
;
 X-Ray crystallographic and spectroscopic properties of eight Schiff
 bases as evidence of the proton transfer reaction. Role of the
 intermolecular hydrogen bond
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              156
_journal_paper_doi               10.1039/c0nj00179a
_journal_volume                  35
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C16 H16 N2 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_name_common
;2-(((1S,2R)-1-hydroxy-1-phenylpropan-2-ylimino)methyl)-4-
nitrophenol
;
_chemical_name_systematic
;
2-[{(1S,2R)-1-hydroxy-1-phenylpropan-2-ylimino}methyl]-4-nitrophenol
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-07-21T21:55:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                93.254(2)
_cell_angle_beta                 100.417(2)
_cell_angle_gamma                92.940(2)
_cell_formula_units_Z            2
_cell_length_a                   6.1083(2)
_cell_length_b                   10.3445(4)
_cell_length_c                   12.3439(5)
_cell_measurement_reflns_used    5803
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      1.018
_cell_measurement_wavelength     0.71073
_cell_volume                     764.38(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.617435E-1
_diffrn_orient_matrix_UB_12      0.166736E-1
_diffrn_orient_matrix_UB_13      -0.783024E-1
_diffrn_orient_matrix_UB_21      -0.545443E-1
_diffrn_orient_matrix_UB_22      0.839541E-1
_diffrn_orient_matrix_UB_23      0.253895E-1
_diffrn_orient_matrix_UB_31      0.145015
_diffrn_orient_matrix_UB_32      0.456721E-1
_diffrn_orient_matrix_UB_33      -0.62939E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7278
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.68
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
The light-atom structure prevented a useful absolute structure parameter.
However, the chirality of the molecule is completely reliable by considering
the enantiomeric purity of the starting material,
(1S,2R)-norephedrine . The Friedel-pairs reflections were
merged in the refinement by using MERG4. Flack H D (1983), Acta Cryst. A39,
876-881.
;
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_coef       0.25(5)
_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   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         3435
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1068P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.1787
_reflns_number_gt                2447
_reflns_number_total             3435
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            C0NJ00179A.TXT
_cod_data_source_block           Compound6
_cod_database_code               7052536