##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-02-07
_journal_date_accepted     2006-02-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      3
_journal_page_first     o1067
_journal_page_last     o1069
_journal_paper_category     EO
_journal_coeditor_code     TK2003
_publ_contact_author_name     'Pedro Silva'
_publ_contact_author_address
; Escola Superior Agrária
  Instituto Politécnico de Castelo Branco
  Quinta da Senhora de Mércules,  Apartado 119
  6001-909 Castelo Branco
  Portugal
;
_publ_contact_author_email     psidonio@esa.ipcb.pt
_publ_contact_author_fax     '351 272339901'
_publ_contact_author_phone     '351 272339952'
_publ_section_title
;
N,N'-Diphenylguanidinium phthalate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Pereira Silva, P. S. ' .
; Escola Superior Agrária
  Instituto Politécnico de Castelo Branco
  Quinta da Senhora de Mércules,  Apartado 119
  6001-909 Castelo Branco
  Portugal
;
    'Ramos Silva, M.' .
; CEMDRX, Departamento de Física
  Faculdade de Ciências e Tecnologia
  Universidade de Coimbra
  P-3004-516 Coimbra
  Portugal
;
    'Matos Beja, A.' .
; CEMDRX, Departamento de Física
  Faculdade de Ciências e Tecnologia
  Universidade de Coimbra
  P-3004-516 Coimbra
  Portugal
;
    'Paixão, J. A.' .
; CEMDRX, Departamento de Física
  Faculdade de Ciências e Tecnologia
  Universidade de Coimbra
  P-3004-516 Coimbra
  Portugal
;
data_I
_chemical_name_systematic
;
N,N'-diphenylguanidinium phthalate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H14 N3 +, C8 H5 O4 -'
_chemical_formula_sum     'C21 H19 N3 O4'
_chemical_formula_iupac     'C13 H14 N3 +, C8 H5 O4 -'
_chemical_formula_weight     377.39
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     10.7714(12)
_cell_length_b     8.440(2)
_cell_length_c     11.420(3)
_cell_angle_alpha     90
_cell_angle_beta     112.172(12)
_cell_angle_gamma     90
_cell_volume     961.4(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     8.2
_cell_measurement_theta_max     12.0
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.34
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.304
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     396
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     'profile data from ω-2θ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5916
_diffrn_reflns_av_R_equivalents     0.031
_diffrn_reflns_av_sigmaI/netI     0.033
_diffrn_reflns_theta_min     3.1
_diffrn_reflns_theta_max     30.1
_diffrn_reflns_theta_full     30.1
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     180
_diffrn_standards_decay_%     3
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2999
_reflns_number_gt     1803
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.086
_refine_ls_R_factor_gt     0.038
_refine_ls_wR_factor_gt     0.096
_refine_ls_wR_factor_ref     0.114
_refine_ls_goodness_of_fit_ref     1.00
_refine_ls_restrained_S_all     1.00
_refine_ls_number_reflns     2999
_refine_ls_number_parameters     256
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0647P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.16
_refine_diff_density_min     -0.22
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software'
_computing_data_reduction     'SDP-Plus (Frenz, 1985)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     'SHELXL97'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.01506(18) 0.0035(3) 0.54850(16) 0.0669(5) Uani d . 1 . .
    H H1 -0.0607 -0.0180 0.5538 0.080 Uiso calc R 1 . .
    N N2 0.10893(19) 0.0115(3) 0.76358(17) 0.0684(6) Uani d . 1 . .
    H H2A 0.1735 0.0367 0.8329 0.082 Uiso calc R 1 . .
    H H2B 0.0389 -0.0352 0.7658 0.082 Uiso calc R 1 . .
    N N3 0.22323(17) 0.1159(3) 0.64597(16) 0.0630(5) Uani d . 1 . .
    H H3A 0.2185 0.1431 0.5718 0.076 Uiso calc R 1 . .
    C C1 0.1173(2) 0.0442(3) 0.65443(19) 0.0574(5) Uani d . 1 . .
    C C2 0.0239(2) -0.0064(3) 0.4280(2) 0.0622(6) Uani d . 1 . .
    C C3 0.1140(3) -0.1055(4) 0.4077(3) 0.0873(8) Uani d . 1 . .
    H H3 0.1738 -0.1637 0.4743 0.105 Uiso calc R 1 . .
    C C4 0.1158(4) -0.1187(5) 0.2887(3) 0.1053(11) Uani d . 1 . .
    H H4 0.1772 -0.1866 0.2754 0.126 Uiso calc R 1 . .
    C C5 0.0316(4) -0.0364(5) 0.1915(3) 0.0970(12) Uani d . 1 . .
    H H5 0.0336 -0.0479 0.1112 0.116 Uiso calc R 1 . .
    C C6 -0.0565(3) 0.0638(6) 0.2108(3) 0.1028(12) Uani d . 1 . .
    H H6 -0.1142 0.1226 0.1434 0.123 Uiso calc R 1 . .
    C C7 -0.0628(2) 0.0809(5) 0.3294(2) 0.0795(8) Uani d . 1 . .
    H H7 -0.1241 0.1497 0.3419 0.095 Uiso calc R 1 . .
    C C8 0.3446(2) 0.1516(3) 0.75027(18) 0.0529(5) Uani d . 1 . .
    C C9 0.3475(2) 0.2564(3) 0.8414(2) 0.0669(6) Uani d . 1 . .
    H H9 0.2689 0.3053 0.8383 0.080 Uiso calc R 1 . .
    C C10 0.4681(3) 0.2902(4) 0.9391(3) 0.0823(8) Uani d . 1 . .
    H H10 0.4702 0.3593 1.0032 0.099 Uiso calc R 1 . .
    C C11 0.5831(3) 0.2225(4) 0.9411(3) 0.0914(9) Uani d . 1 . .
    H H11 0.6641 0.2468 1.0060 0.110 Uiso calc R 1 . .
    C C12 0.5807(3) 0.1193(4) 0.8488(3) 0.0919(10) Uani d . 1 . .
    H H12 0.6601 0.0744 0.8503 0.110 Uiso calc R 1 . .
    C C13 0.4609(2) 0.0811(4) 0.7532(3) 0.0714(6) Uani d . 1 . .
    H H13 0.4586 0.0083 0.6912 0.086 Uiso calc R 1 . .
    O O4 0.20405(13) 0.3301(2) 0.44567(13) 0.0607(4) Uani d . 1 . .
    O O3 0.15213(17) 0.4138(3) 0.25175(17) 0.0775(5) Uani d . 1 . .
    O O2 0.15715(18) 0.2810(3) 0.06339(16) 0.0867(6) Uani d . 1 . .
    H H2 0.150(3) 0.345(5) 0.129(3) 0.104 Uiso d . 1 . .
    O O1 0.25127(19) 0.0681(3) 0.02766(15) 0.0848(6) Uani d . 1 . .
    C C14 0.34142(18) 0.2427(3) 0.33978(17) 0.0479(4) Uani d . 1 . .
    C C15 0.44885(19) 0.2272(3) 0.45412(19) 0.0562(5) Uani d . 1 . .
    H H15 0.4423 0.2701 0.5266 0.067 Uiso calc R 1 . .
    C C16 0.5650(2) 0.1502(4) 0.4635(2) 0.0662(6) Uani d . 1 . .
    H H16 0.6357 0.1416 0.5414 0.079 Uiso calc R 1 . .
    C C17 0.5756(2) 0.0863(4) 0.3577(2) 0.0708(6) Uani d . 1 . .
    H H17 0.6543 0.0360 0.3629 0.085 Uiso calc R 1 . .
    C C18 0.4697(2) 0.0968(3) 0.2439(2) 0.0641(6) Uani d . 1 . .
    H H18 0.4767 0.0502 0.1728 0.077 Uiso calc R 1 . .
    C C19 0.35186(19) 0.1755(3) 0.23207(18) 0.0512(5) Uani d . 1 . .
    C C20 0.22337(19) 0.3330(3) 0.34626(19) 0.0534(5) Uani d . 1 . .
    C C21 0.2475(2) 0.1704(4) 0.0998(2) 0.0636(6) Uani d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C1 . 1.337(3) ?
    N1 C2 . 1.417(3) yes
    N1 H1 . 0.8600 ?
    N2 C1 . 1.313(3) ?
    N2 H2A . 0.8600 ?
    N2 H2B . 0.8600 ?
    N3 C1 . 1.327(3) ?
    N3 C8 . 1.429(3) yes
    N3 H3A . 0.8600 ?
    C2 C3 . 1.365(4) ?
    C2 C7 . 1.374(4) ?
    C3 C4 . 1.372(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.333(6) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.351(5) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.389(4) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.357(3) ?
    C8 C13 . 1.376(3) ?
    C9 C10 . 1.386(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.356(4) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.360(5) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.378(4) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    O4 C20 . 1.229(2) yes
    O3 C20 . 1.262(3) yes
    O2 C21 . 1.299(3) yes
    O2 H2 . 0.95(4) ?
    O1 C21 . 1.205(3) yes
    C14 C15 . 1.386(3) ?
    C14 C19 . 1.397(3) ?
    C14 C20 . 1.508(3) ?
    C15 C16 . 1.377(3) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.367(3) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.371(3) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.394(3) ?
    C18 H18 . 0.9300 ?
    C19 C21 . 1.505(3) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 N1 C2 . . 123.99(17) ?
    C1 N1 H1 . . 118.0 ?
    C2 N1 H1 . . 118.0 ?
    C1 N2 H2A . . 120.0 ?
    C1 N2 H2B . . 120.0 ?
    H2A N2 H2B . . 120.0 ?
    C1 N3 C8 . . 125.21(17) ?
    C1 N3 H3A . . 117.4 ?
    C8 N3 H3A . . 117.4 ?
    N2 C1 N3 . . 122.3(2) ?
    N2 C1 N1 . . 118.47(18) yes
    N3 C1 N1 . . 119.24(18) yes
    C3 C2 C7 . . 119.7(2) ?
    C3 C2 N1 . . 120.9(2) ?
    C7 C2 N1 . . 119.3(2) ?
    C2 C3 C4 . . 119.7(3) ?
    C2 C3 H3 . . 120.2 ?
    C4 C3 H3 . . 120.2 ?
    C5 C4 C3 . . 121.6(4) ?
    C5 C4 H4 . . 119.2 ?
    C3 C4 H4 . . 119.2 ?
    C4 C5 C6 . . 119.3(3) ?
    C4 C5 H5 . . 120.3 ?
    C6 C5 H5 . . 120.3 ?
    C5 C6 C7 . . 121.3(3) ?
    C5 C6 H6 . . 119.3 ?
    C7 C6 H6 . . 119.3 ?
    C2 C7 C6 . . 118.4(3) ?
    C2 C7 H7 . . 120.8 ?
    C6 C7 H7 . . 120.8 ?
    C9 C8 C13 . . 120.4(2) ?
    C9 C8 N3 . . 121.70(19) ?
    C13 C8 N3 . . 117.8(2) ?
    C8 C9 C10 . . 119.7(2) ?
    C8 C9 H9 . . 120.2 ?
    C10 C9 H9 . . 120.2 ?
    C11 C10 C9 . . 120.0(3) ?
    C11 C10 H10 . . 120.0 ?
    C9 C10 H10 . . 120.0 ?
    C10 C11 C12 . . 120.4(3) ?
    C10 C11 H11 . . 119.8 ?
    C12 C11 H11 . . 119.8 ?
    C11 C12 C13 . . 120.2(3) ?
    C11 C12 H12 . . 119.9 ?
    C13 C12 H12 . . 119.9 ?
    C8 C13 C12 . . 119.3(3) ?
    C8 C13 H13 . . 120.3 ?
    C12 C13 H13 . . 120.3 ?
    C21 O2 H2 . . 116(2) ?
    C15 C14 C19 . . 118.37(18) ?
    C15 C14 C20 . . 114.91(17) ?
    C19 C14 C20 . . 126.72(17) ?
    C16 C15 C14 . . 121.9(2) ?
    C16 C15 H15 . . 119.0 ?
    C14 C15 H15 . . 119.0 ?
    C17 C16 C15 . . 119.6(2) ?
    C17 C16 H16 . . 120.2 ?
    C15 C16 H16 . . 120.2 ?
    C16 C17 C18 . . 119.7(2) ?
    C16 C17 H17 . . 120.1 ?
    C18 C17 H17 . . 120.1 ?
    C17 C18 C19 . . 121.6(2) ?
    C17 C18 H18 . . 119.2 ?
    C19 C18 H18 . . 119.2 ?
    C18 C19 C14 . . 118.79(18) ?
    C18 C19 C21 . . 113.05(19) ?
    C14 C19 C21 . . 128.12(18) ?
    O4 C20 O3 . . 122.7(2) yes
    O4 C20 C14 . . 118.35(18) ?
    O3 C20 C14 . . 118.87(17) ?
    O1 C21 O2 . . 120.7(2) yes
    O1 C21 C19 . . 120.1(2) ?
    O2 C21 C19 . . 119.1(2) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C8 N3 C1 N2 . . . . 6.7(4) yes
    C8 N3 C1 N1 . . . . -173.4(2) yes
    C2 N1 C1 N2 . . . . -163.0(3) yes
    C2 N1 C1 N3 . . . . 17.1(4) yes
    C1 N1 C2 C3 . . . . 58.5(4) ?
    C1 N1 C2 C7 . . . . -123.8(3) ?
    C7 C2 C3 C4 . . . . -1.0(5) ?
    N1 C2 C3 C4 . . . . 176.7(3) ?
    C2 C3 C4 C5 . . . . 0.2(6) ?
    C3 C4 C5 C6 . . . . 0.8(6) ?
    C4 C5 C6 C7 . . . . -1.1(6) ?
    C3 C2 C7 C6 . . . . 0.7(4) ?
    N1 C2 C7 C6 . . . . -177.0(3) ?
    C5 C6 C7 C2 . . . . 0.4(5) ?
    C1 N3 C8 C9 . . . . -65.4(3) ?
    C1 N3 C8 C13 . . . . 117.3(3) ?
    C13 C8 C9 C10 . . . . -1.2(4) ?
    N3 C8 C9 C10 . . . . -178.4(2) ?
    C8 C9 C10 C11 . . . . 2.1(4) ?
    C9 C10 C11 C12 . . . . -1.1(5) ?
    C10 C11 C12 C13 . . . . -0.9(5) ?
    C9 C8 C13 C12 . . . . -0.7(4) ?
    N3 C8 C13 C12 . . . . 176.6(2) ?
    C11 C12 C13 C8 . . . . 1.8(4) ?
    C19 C14 C15 C16 . . . . 1.0(3) ?
    C20 C14 C15 C16 . . . . -178.9(2) ?
    C14 C15 C16 C17 . . . . -0.2(4) ?
    C15 C16 C17 C18 . . . . -1.3(4) ?
    C16 C17 C18 C19 . . . . 2.0(4) ?
    C17 C18 C19 C14 . . . . -1.1(4) ?
    C17 C18 C19 C21 . . . . -178.9(3) ?
    C15 C14 C19 C18 . . . . -0.4(3) ?
    C20 C14 C19 C18 . . . . 179.5(2) ?
    C15 C14 C19 C21 . . . . 177.0(2) ?
    C20 C14 C19 C21 . . . . -3.0(4) ?
    C15 C14 C20 O4 . . . . -28.7(3) ?
    C19 C14 C20 O4 . . . . 151.3(2) ?
    C15 C14 C20 O3 . . . . 148.2(2) ?
    C19 C14 C20 O3 . . . . -31.7(3) ?
    C18 C19 C21 O1 . . . . 22.3(3) ?
    C14 C19 C21 O1 . . . . -155.3(2) ?
    C18 C19 C21 O2 . . . . -155.0(2) ?
    C14 C19 C21 O2 . . . . 27.5(4) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1 O4 2_546 0.86 2.01 2.799(2) 152
    N2 H2A O1 1_556 0.86 2.08 2.861(3) 151
    N3 H3A O4 . 0.86 2.10 2.861(3) 147
    O2 H2 O3 . 0.95(4) 1.51(4) 2.444(3) 167(4)
