Molecular Complexes of DiethylN,N′-1,3-Phenyldioxalamate and Resorcinols: Conformational Switching through Intramolecular Three-Centered Hydrogen-Bonding
González-González, Juan Saulo; Martínez-Martínez, Francisco J.; García-Báez, Efrén V.; Cruz, Alejandro; Morín-Sánchez, Luis M.; Rojas-Lima, Susana; Padilla-Martínez, Itzia I.; Crystal Growth & Design 14 (2014) 628–; doi:10.1021/cg401500k

data_4509882
_publ_contact_author
;
      "Itzia I. Padilla-Mart\'inez"
      Unidad Profesional Interdisciplinaria de Biotecnolog\'ia
      Instituto Polit\'ecnico Nacional
      Avenida Acueducto s/n
      Barrio La Laguna Ticom\'an
      M\'exico D. F. 07340, M\'exico.
;
_publ_section_related_literature
;
?
;
_publ_section_title
;
 Molecular Complexes of DiethylN,N&#x2032;-1,3-Phenyldioxalamate and
 Resorcinols: Conformational Switching through Intramolecular
 Three-Centered Hydrogen-Bonding
;
_journal_issue                   2
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              628
_journal_paper_doi               10.1021/cg401500k
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C21 H24 N2 O8'
_chemical_formula_weight         432.42
_chemical_name_systematic
;
5-Methyl-1,3-benzenediol-diethyl N,N'-(1,3-phenylene)
dioxalamate complex 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_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                 97.223(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.9410(2)
_cell_length_b                   18.7803(5)
_cell_length_c                   11.2062(4)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      20
_cell_volume                     1031.61(6)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'Mercury 2.4 (Macrae <i>et al</i>., 2006)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008)/WINGX-2003 (Farrugia, 1999)/PublCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.434
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Ruby Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10094
_diffrn_reflns_theta_full        73.51
_diffrn_reflns_theta_max         73.51
_diffrn_reflns_theta_min         3.98
_exptl_absorpt_coefficient_mu    0.908
_exptl_absorpt_correction_T_max  0.8643
_exptl_absorpt_correction_T_min  0.8614
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
Interpolation using  Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975)
A31,146-148) is used with some modification.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_size_rad          0.1200
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0598P)^2^+0.2348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                1668
_reflns_number_total             2092
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401500k_si_002.cif
_cod_data_source_block           SRL37
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4509882
_exptl_absorpt_correction_t_ave  0.8629