##############################################################################
###                                                                        ###
###        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/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
Guanidinum diphenylphosphinate monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C H6 N3 + , C12 H10 O2 P - , H2 O'
_chemical_formula_sum     'C13 H18 N3 O3 P'
_chemical_formula_iupac     'C H6 N3 + , C12 H10 O2 P - , H2 O'
_chemical_formula_weight     295.27
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     11.2395(10)
_cell_length_b     10.0101(9)
_cell_length_c     12.9814(12)
_cell_angle_alpha     90.00
_cell_angle_beta     98.653(2)
_cell_angle_gamma     90.00
_cell_volume     1443.9(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5028
_cell_measurement_theta_min     2.58
_cell_measurement_theta_max     28.81
_cell_measurement_temperature     150(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.358
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     624
_exptl_absorpt_coefficient_mu     0.201
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.85
_exptl_absorpt_correction_T_max     0.96
_exptl_special_details
; Spectroscopic analysis: IR (KBr, ν, cm⁻¹) inter alia: 3473 (m,
sharp), 3228 (s, br), 1662 (s), 1438 (m), 1152
(m), 1126 (m). Analysis calculated for
(CH₆N)(C₁₂H₁₀O₂P)(H₂O): C 52.9, H 6.1, N 14.2%; found: C 51.5, H
6.1, N 14.2%.
;
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'normal-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11089
_diffrn_reflns_av_R_equivalents     0.0279
_diffrn_reflns_av_sigmaI/netI     0.0249
_diffrn_reflns_theta_min     1.83
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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     2839
_reflns_number_gt     2376
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0441
_refine_ls_R_factor_gt     0.0356
_refine_ls_wR_factor_gt     0.0883
_refine_ls_wR_factor_ref     0.0943
_refine_ls_goodness_of_fit_ref     1.043
_refine_ls_restrained_S_all     1.043
_refine_ls_number_reflns     2839
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0468P)²+0.6736P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.322
_refine_diff_density_min     -0.347
_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'
    'P' 'P' 0.1023 0.0942
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1998)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics
                              'SHELXTL and MERCURY (Bruno et al.,  2002)'
_computing_publication_material     'SHELXTL'
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
    P P1 0.79796(4) 0.67583(4) 0.17036(3) 0.01833(13) Uani d . 1 . .
    O O1 0.83595(11) 0.57444(11) 0.25453(8) 0.0236(3) Uani d . 1 . .
    O O2 0.88275(10) 0.79023(11) 0.15923(9) 0.0227(3) Uani d . 1 . .
    C C11 0.77115(15) 0.59049(16) 0.04612(12) 0.0193(3) Uani d . 1 . .
    C C12 0.66859(15) 0.51252(17) 0.01707(13) 0.0230(4) Uani d . 1 . .
    H H12 0.6107 0.5045 0.0631 0.028 Uiso calc R 1 . .
    C C13 0.64994(16) 0.44662(17) -0.07783(13) 0.0258(4) Uani d . 1 . .
    H H13 0.5791 0.3951 -0.0970 0.031 Uiso calc R 1 . .
    C C14 0.73516(16) 0.45604(17) -0.14498(13) 0.0258(4) Uani d . 1 . .
    H H14 0.7222 0.4117 -0.2104 0.031 Uiso calc R 1 . .
    C C15 0.83878(16) 0.53014(18) -0.11620(13) 0.0275(4) Uani d . 1 . .
    H H15 0.8979 0.5349 -0.1612 0.033 Uiso calc R 1 . .
    C C16 0.85656(16) 0.59763(17) -0.02159(13) 0.0237(4) Uani d . 1 . .
    H H16 0.9275 0.6491 -0.0027 0.028 Uiso calc R 1 . .
    C C21 0.65394(14) 0.74541(16) 0.18905(12) 0.0204(4) Uani d . 1 . .
    C C22 0.60393(15) 0.71836(17) 0.27863(13) 0.0239(4) Uani d . 1 . .
    H H22 0.6443 0.6595 0.3298 0.029 Uiso calc R 1 . .
    C C23 0.49556(16) 0.77648(19) 0.29409(15) 0.0292(4) Uani d . 1 . .
    H H23 0.4624 0.7574 0.3556 0.035 Uiso calc R 1 . .
    C C24 0.43604(16) 0.86223(19) 0.21980(15) 0.0305(4) Uani d . 1 . .
    H H24 0.3621 0.9021 0.2303 0.037 Uiso calc R 1 . .
    C C25 0.48457(17) 0.88968(19) 0.13031(15) 0.0313(4) Uani d . 1 . .
    H H25 0.4436 0.9482 0.0792 0.038 Uiso calc R 1 . .
    C C26 0.59263(16) 0.83230(17) 0.11475(13) 0.0257(4) Uani d . 1 . .
    H H26 0.6254 0.8521 0.0532 0.031 Uiso calc R 1 . .
    C C1 0.84951(15) 0.42953(17) 0.51824(13) 0.0211(4) Uani d . 1 . .
    N N1 0.84711(15) 0.31513(16) 0.46534(13) 0.0287(4) Uani d . 1 . .
    N N2 0.85314(14) 0.54552(15) 0.47013(12) 0.0260(3) Uani d . 1 . .
    N N3 0.84615(15) 0.42724(17) 0.61987(12) 0.0285(4) Uani d . 1 . .
    O O1W 0.88781(12) 0.31041(13) 0.24274(11) 0.0299(3) Uani d . 1 . .
    H H1A 0.8343(19) 0.243(2) 0.4964(17) 0.040 Uiso d . 1 . .
    H H1B 0.8498(19) 0.317(2) 0.3955(18) 0.040 Uiso d . 1 . .
    H H2A 0.8634(19) 0.615(2) 0.5120(17) 0.040 Uiso d . 1 . .
    H H2B 0.8496(19) 0.552(2) 0.4010(18) 0.040 Uiso d . 1 . .
    H H3A 0.8597(19) 0.352(2) 0.6541(17) 0.040 Uiso d . 1 . .
    H H3B 0.8528(19) 0.509(2) 0.6505(17) 0.040 Uiso d . 1 . .
    H H1WA 0.8740(19) 0.394(2) 0.2340(17) 0.040 Uiso d . 1 . .
    H H1WB 0.963(2) 0.302(2) 0.2650(17) 0.040 Uiso d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    P1 0.0214(2) 0.0171(2) 0.0164(2) 0.00022(16) 0.00256(16) 0.00037(16)
    O1 0.0308(7) 0.0209(6) 0.0190(6) 0.0036(5) 0.0030(5) 0.0017(5)
    O2 0.0237(6) 0.0221(6) 0.0219(6) -0.0034(5) 0.0023(5) -0.0005(5)
    C11 0.0237(9) 0.0162(8) 0.0179(8) 0.0015(6) 0.0029(6) 0.0022(6)
    C12 0.0238(9) 0.0223(9) 0.0236(9) -0.0008(7) 0.0056(7) -0.0015(7)
    C13 0.0245(9) 0.0220(9) 0.0296(9) 0.0007(7) -0.0001(7) -0.0044(7)
    C14 0.0343(10) 0.0240(9) 0.0187(8) 0.0041(7) 0.0028(7) -0.0025(7)
    C15 0.0332(10) 0.0285(10) 0.0227(9) 0.0005(8) 0.0103(7) -0.0006(7)
    C16 0.0240(9) 0.0236(9) 0.0237(9) -0.0016(7) 0.0047(7) 0.0009(7)
    C21 0.0225(8) 0.0168(8) 0.0216(9) -0.0013(6) 0.0021(7) -0.0034(6)
    C22 0.0276(9) 0.0221(9) 0.0223(9) -0.0004(7) 0.0045(7) -0.0009(7)
    C23 0.0301(10) 0.0298(10) 0.0295(10) -0.0051(8) 0.0107(8) -0.0063(8)
    C24 0.0254(9) 0.0283(10) 0.0382(11) 0.0018(8) 0.0063(8) -0.0104(8)
    C25 0.0297(10) 0.0277(10) 0.0355(10) 0.0061(8) 0.0013(8) 0.0022(8)
    C26 0.0286(9) 0.0240(9) 0.0252(9) 0.0023(7) 0.0060(7) 0.0018(7)
    C1 0.0193(8) 0.0236(9) 0.0204(8) 0.0013(6) 0.0030(6) -0.0018(7)
    N1 0.0380(9) 0.0235(8) 0.0256(8) -0.0027(7) 0.0078(7) -0.0039(6)
    N2 0.0376(9) 0.0227(8) 0.0176(7) 0.0010(6) 0.0038(6) -0.0003(6)
    N3 0.0438(10) 0.0224(8) 0.0200(8) 0.0042(7) 0.0070(7) 0.0029(6)
    O1W 0.0263(7) 0.0213(7) 0.0398(8) 0.0030(5) -0.0019(6) -0.0037(6)
_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
    P1 O1 . 1.5053(12) ?
    P1 O2 . 1.5105(12) ?
    P1 C11 . 1.8099(16) ?
    P1 C21 . 1.8117(17) ?
    C11 C12 . 1.396(2) ?
    C11 C16 . 1.397(2) ?
    C12 C13 . 1.385(2) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.392(2) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.384(2) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.390(2) ?
    C15 H15 . 0.9500 ?
    C16 H16 . 0.9500 ?
    C21 C22 . 1.392(2) ?
    C21 C26 . 1.401(2) ?
    C22 C23 . 1.391(2) ?
    C22 H22 . 0.9500 ?
    C23 C24 . 1.386(3) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.383(3) ?
    C24 H24 . 0.9500 ?
    C25 C26 . 1.385(2) ?
    C25 H25 . 0.9500 ?
    C26 H26 . 0.9500 ?
    C1 N2 . 1.322(2) ?
    C1 N3 . 1.326(2) ?
    C1 N1 . 1.333(2) ?
    C1 N2 3_766 3.332(2) ?
    N1 H1A . 0.85(2) ?
    N1 H1B . 0.91(2) ?
    N2 H2A . 0.88(2) ?
    N2 H2B . 0.89(2) ?
    N3 H3A . 0.88(2) ?
    N3 H3B . 0.90(2) ?
    O1W H1WA . 0.86(2) ?
    O1W H1WB . 0.86(2) ?
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
    O1 P1 O2 . . 117.80(7) ?
    O1 P1 C11 . . 108.64(7) ?
    O2 P1 C11 . . 107.18(7) ?
    O1 P1 C21 . . 108.88(7) ?
    O2 P1 C21 . . 108.10(7) ?
    C11 P1 C21 . . 105.57(7) ?
    C12 C11 C16 . . 118.43(15) ?
    C12 C11 P1 . . 121.64(12) ?
    C16 C11 P1 . . 119.89(13) ?
    C13 C12 C11 . . 120.98(16) ?
    C13 C12 H12 . . 119.5 ?
    C11 C12 H12 . . 119.5 ?
    C12 C13 C14 . . 119.89(16) ?
    C12 C13 H13 . . 120.1 ?
    C14 C13 H13 . . 120.1 ?
    C15 C14 C13 . . 119.85(16) ?
    C15 C14 H14 . . 120.1 ?
    C13 C14 H14 . . 120.1 ?
    C14 C15 C16 . . 120.16(16) ?
    C14 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C15 C16 C11 . . 120.66(16) ?
    C15 C16 H16 . . 119.7 ?
    C11 C16 H16 . . 119.7 ?
    C22 C21 C26 . . 118.51(16) ?
    C22 C21 P1 . . 121.21(13) ?
    C26 C21 P1 . . 120.23(13) ?
    C23 C22 C21 . . 120.75(17) ?
    C23 C22 H22 . . 119.6 ?
    C21 C22 H22 . . 119.6 ?
    C24 C23 C22 . . 120.01(17) ?
    C24 C23 H23 . . 120.0 ?
    C22 C23 H23 . . 120.0 ?
    C25 C24 C23 . . 119.83(17) ?
    C25 C24 H24 . . 120.1 ?
    C23 C24 H24 . . 120.1 ?
    C24 C25 C26 . . 120.35(17) ?
    C24 C25 H25 . . 119.8 ?
    C26 C25 H25 . . 119.8 ?
    C25 C26 C21 . . 120.55(16) ?
    C25 C26 H26 . . 119.7 ?
    C21 C26 H26 . . 119.7 ?
    N2 C1 N3 . . 119.52(16) ?
    N2 C1 N1 . . 120.71(16) ?
    N3 C1 N1 . . 119.75(17) ?
    N2 C1 N2 . 3_766 81.58(11) ?
    N3 C1 N2 . 3_766 97.74(11) ?
    N1 C1 N2 . 3_766 91.73(11) ?
    C1 N1 H1A . . 118.3(15) ?
    C1 N1 H1B . . 119.8(13) ?
    H1A N1 H1B . . 121(2) ?
    C1 N2 H2A . . 114.6(14) ?
    C1 N2 H2B . . 122.6(14) ?
    H2A N2 H2B . . 123(2) ?
    C1 N3 H3A . . 119.4(14) ?
    C1 N3 H3B . . 114.1(14) ?
    H3A N3 H3B . . 124(2) ?
    H1WA O1W H1WB . . 107(2) ?
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
    _geom_hbond_publ_flag
    N1 H1B O1W . 0.91(2) 2.09(2) 2.993(2) 169.9(19) y
    N2 H2B O1 . 0.89(2) 1.90(2) 2.7914(19) 177(2) y
    N2 H2A O2 4_576 0.88(2) 2.11(2) 2.932(2) 153.8(19) y
    N3 H3B O2 4_576 0.90(2) 2.04(2) 2.892(2) 156.1(19) y
    N3 H3A O1W 4_566 0.88(2) 1.99(2) 2.863(2) 175(2) y
    O1W H1WA O1 . 0.86(2) 1.88(2) 2.7157(18) 164(2) y
    O1W H1WB O2 2_745 0.86(2) 1.86(2) 2.7061(18) 168(2) y
data_global
_journal_date_recd_electronic     2006-02-24
_journal_date_accepted     2006-03-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      4
_journal_page_first     o1365
_journal_page_last     o1368
_journal_paper_category     EO
_journal_coeditor_code     LH2012
_publ_contact_author_name     'Vickie McKee'
_publ_contact_author_address
;
Chemistry Department
Loughborough University
Loughborough
Leicsestershire LE11 3TU
England
;
_publ_contact_author_email     v.mckee@lboro.ac.uk
_publ_contact_author_fax     '01509 223925'
_publ_contact_author_phone     '01509 222565'
_publ_section_title
;
Guanidinum diphenylphosphinate monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Najafpour, M. Mahdi'
;
Dorna Institute of Science
Ahwaz
Khozestan
Iran
;
    'McKee, Vickie'
;
Chemistry Department
Loughborough University
Loughborough
Leicestershire LE11 3TU
England
;
