##############################################################################
###                                                                        ###
###        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_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2004-10-25
_journal_date_accepted     2004-11-01
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue     12
_journal_page_first     o2232
_journal_page_last     o2234
_journal_paper_category     EO
_publ_contact_author_name     'Craig C. McLauchlan'
_publ_contact_author_address
; Department of Chemistry
  Illinois State University
  Campus Box 4160
  Normal, IL 61790-4160, USA
;
_publ_contact_author_email     mclauchlan@ilstu.edu
_publ_contact_author_fax     '(309)438-5538'
_publ_contact_author_phone     '(309)438-7019'
_publ_section_title
;
Bis[3-(trimethylsilyl)propyl] methylenebisphosphonate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'McLauchlan, Craig C.' .
;
Department of Chemistry
Illinois State University
Campus Box 4160
Normal
IL 61790-4160
USA
;
    'Stepinski, Dominique C.' .
;
Department of Chemistry
Loyola University Chicago
Chicago
IL 60626
USA
;
    'Herlinger, Albert W.' .
;
Department of Chemistry
Loyola University Chicago
Chicago
IL 60626
USA
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Bis[3-(trimethylsilyl)propyl] methylenebisphosphonate
;
_chemical_formula_moiety     'C13 H34 O6 P2 Si2'
_chemical_formula_sum     'C13 H34 O6 P2 Si2'
_chemical_formula_iupac     'C13 H34 O6 P2 Si2'
_chemical_formula_weight     404.52
_chemical_melting_point     313.0(10)
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.534(2)
_cell_length_b     11.130(2)
_cell_length_c     16.325(2)
_cell_angle_alpha     100.640(10)
_cell_angle_beta     100.250(10)
_cell_angle_gamma     106.23(2)
_cell_volume     1086.6(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3959
_cell_measurement_theta_min     1.7559
_cell_measurement_theta_max     29.4232
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.36465
_exptl_crystal_size_mid     0.13321
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.236
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     436
_exptl_absorpt_coefficient_mu     0.332
_exptl_absorpt_correction_type     'numerical'
_exptl_absorpt_process_details     '(Clark & Reid, 1995)'
_exptl_absorpt_correction_T_min     0.88844
_exptl_absorpt_correction_T_max     0.98329
_exptl_special_details
;
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark & Reid, 1995)
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur3 diffractometer equipped with a CCD detector
;
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10850
_diffrn_reflns_av_R_equivalents     0.0463
_diffrn_reflns_av_sigmaI/netI     0.0556
_diffrn_reflns_theta_min     4.20
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     <1
_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     4971
_reflns_number_gt     3556
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0815
_refine_ls_R_factor_gt     0.0607
_refine_ls_wR_factor_gt     0.1591
_refine_ls_wR_factor_ref     0.1780
_refine_ls_goodness_of_fit_ref     1.148
_refine_ls_restrained_S_all     1.148
_refine_ls_number_reflns     4971
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                'calc w = 1/[σ²(Fo²)+(0.1P)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     0.998
_refine_diff_density_min     -0.573
_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'
    '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'
    'Si' 'Si' 0.0817 0.0704
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2004)
;
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2004)
;
_computing_data_reduction
;
CrysAlis RED
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _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
    _atom_site_type_symbol
    C1 0.7308(4) 0.9586(3) 0.07610(19) 0.0266(7) Uani d . 1 . . C
    H1A 0.7430 1.0399 0.0606 0.032 Uiso calc R 1 . . H
    H1B 0.7628 0.9020 0.0309 0.032 Uiso calc R 1 . . H
    C2 0.8949(5) 0.9821(3) 0.15949(18) 0.0245(6) Uani d . 1 . . C
    H2A 0.9009 0.8998 0.1696 0.029 Uiso calc R 1 . . H
    H2B 0.8467 1.0247 0.2062 0.029 Uiso calc R 1 . . H
    C3 1.1261(5) 1.0657(3) 0.15930(18) 0.0236(6) Uani d . 1 . . C
    H3A 1.1167 1.1447 0.1443 0.028 Uiso calc R 1 . . H
    H3B 1.1776 1.0197 0.1152 0.028 Uiso calc R 1 . . H
    C4 1.2286(5) 1.1882(4) 0.3517(2) 0.0333(7) Uani d . 1 . . C
    H4A 1.0940 1.1293 0.3557 0.050 Uiso calc R 1 . . H
    H4B 1.2025 1.2642 0.3389 0.050 Uiso calc R 1 . . H
    H4C 1.3359 1.2118 0.4053 0.050 Uiso calc R 1 . . H
    C5 1.3742(5) 0.9597(3) 0.2894(2) 0.0306(7) Uani d . 1 . . C
    H5A 1.4199 0.9152 0.2435 0.046 Uiso calc R 1 . . H
    H5B 1.2389 0.9045 0.2957 0.046 Uiso calc R 1 . . H
    H5C 1.4852 0.9824 0.3419 0.046 Uiso calc R 1 . . H
    C6 1.5974(5) 1.2221(3) 0.2584(2) 0.0290(7) Uani d . 1 . . C
    H6A 1.7099 1.2322 0.3082 0.043 Uiso calc R 1 . . H
    H6B 1.5806 1.3046 0.2563 0.043 Uiso calc R 1 . . H
    H6C 1.6381 1.1879 0.2076 0.043 Uiso calc R 1 . . H
    C7 0.0968(5) 0.4456(3) 0.21447(19) 0.0249(6) Uani d . 1 . . C
    H7A 0.1727 0.3831 0.2207 0.030 Uiso calc R 1 . . H
    H7B -0.0511 0.4000 0.1794 0.030 Uiso calc R 1 . . H
    C8 0.0894(5) 0.5167(3) 0.30150(18) 0.0232(6) Uani d . 1 . . C
    H8A 0.2387 0.5619 0.3353 0.028 Uiso calc R 1 . . H
    H8B 0.0203 0.4542 0.3308 0.028 Uiso calc R 1 . . H
    C9 -0.0351(5) 0.6139(3) 0.29746(18) 0.0233(6) Uani d . 1 . . C
    H9A -0.1772 0.5707 0.2572 0.028 Uiso calc R 1 . . H
    H9B 0.0452 0.6821 0.2747 0.028 Uiso calc R 1 . . H
    C10 0.1891(6) 0.7757(4) 0.4815(2) 0.0385(8) Uani d . 1 . . C
    H10A 0.2669 0.7157 0.4901 0.058 Uiso calc R 1 . . H
    H10B 0.1637 0.8130 0.5351 0.058 Uiso calc R 1 . . H
    H10C 0.2751 0.8427 0.4603 0.058 Uiso calc R 1 . . H
    C11 -0.2517(5) 0.5594(3) 0.4417(2) 0.0327(7) Uani d . 1 . . C
    H11A -0.3837 0.5110 0.3981 0.049 Uiso calc R 1 . . H
    H11B -0.2889 0.5977 0.4923 0.049 Uiso calc R 1 . . H
    H11C -0.1708 0.5029 0.4555 0.049 Uiso calc R 1 . . H
    C12 -0.2285(6) 0.8063(4) 0.3837(2) 0.0378(8) Uani d . 1 . . C
    H12A -0.1419 0.8721 0.3618 0.057 Uiso calc R 1 . . H
    H12B -0.2530 0.8452 0.4370 0.057 Uiso calc R 1 . . H
    H12C -0.3672 0.7618 0.3429 0.057 Uiso calc R 1 . . H
    C13 0.5061(5) 0.6658(3) 0.10563(18) 0.0217(6) Uani d . 1 . . C
    H13A 0.6340 0.6576 0.0856 0.026 Uiso calc R 1 . . H
    H13B 0.5577 0.7169 0.1647 0.026 Uiso calc R 1 . . H
    O1 0.3779(3) 0.7121(2) -0.04950(12) 0.0251(5) Uani d . 1 . . O
    O2 0.1511(3) 0.7452(2) 0.05977(13) 0.0249(5) Uani d . 1 . . O
    H2 0.0683 0.6704 0.0423 0.037 Uiso calc R 1 . . H
    O3 0.5065(3) 0.89973(19) 0.08340(13) 0.0228(4) Uani d . 1 . . O
    O4 0.1958(3) 0.4386(2) 0.01683(13) 0.0244(5) Uani d . 1 . . O
    O5 0.4835(3) 0.4356(2) 0.14237(12) 0.0246(5) Uani d . 1 . . O
    H5 0.5660 0.4247 0.1113 0.037 Uiso calc R 1 . . H
    O6 0.2130(3) 0.5408(2) 0.17442(13) 0.0277(5) Uani d . 1 . . O
    P1 0.37690(11) 0.75255(7) 0.04168(5) 0.0198(2) Uani d . 1 . . P
    P2 0.33550(12) 0.50793(7) 0.10407(5) 0.0200(2) Uani d . 1 . . P
    Si1 1.33252(13) 1.10894(8) 0.26433(5) 0.0212(2) Uani d . 1 . . Si
    Si2 -0.08000(13) 0.68904(8) 0.40161(5) 0.0236(2) Uani d . 1 . . Si
_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
    C1 O3 . 1.464(3) ?
    C1 C2 . 1.505(4) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 C3 . 1.538(4) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 Si1 . 1.871(3) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 Si1 . 1.867(3) ?
    C4 H4A . 0.9600 ?
    C4 H4B . 0.9600 ?
    C4 H4C . 0.9600 ?
    C5 Si1 . 1.862(3) ?
    C5 H5A . 0.9600 ?
    C5 H5B . 0.9600 ?
    C5 H5C . 0.9600 ?
    C6 Si1 . 1.865(3) ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C7 O6 . 1.453(3) ?
    C7 C8 . 1.509(4) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C9 . 1.529(4) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 Si2 . 1.861(3) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 Si2 . 1.869(4) ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 Si2 . 1.864(3) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 Si2 . 1.865(3) ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C13 P2 . 1.791(3) ?
    C13 P1 . 1.803(3) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    O1 P1 . 1.475(2) y
    O2 P1 . 1.539(2) y
    O2 H2 . 0.8200 ?
    O3 P1 . 1.572(2) y
    O4 P2 . 1.481(2) y
    O5 P2 . 1.543(2) y
    O5 H5 . 0.8200 ?
    O6 P2 . 1.559(2) y
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
    O3 C1 C2 . . 110.9(2) ?
    O3 C1 H1A . . 109.5 ?
    C2 C1 H1A . . 109.5 ?
    O3 C1 H1B . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 108.1 ?
    C1 C2 C3 . . 112.1(2) ?
    C1 C2 H2A . . 109.2 ?
    C3 C2 H2A . . 109.2 ?
    C1 C2 H2B . . 109.2 ?
    C3 C2 H2B . . 109.2 ?
    H2A C2 H2B . . 107.9 ?
    C2 C3 Si1 . . 114.02(19) ?
    C2 C3 H3A . . 108.7 ?
    Si1 C3 H3A . . 108.7 ?
    C2 C3 H3B . . 108.7 ?
    Si1 C3 H3B . . 108.7 ?
    H3A C3 H3B . . 107.6 ?
    Si1 C4 H4A . . 109.5 ?
    Si1 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    Si1 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    Si1 C5 H5A . . 109.5 ?
    Si1 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    Si1 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    Si1 C6 H6A . . 109.5 ?
    Si1 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    Si1 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    O6 C7 C8 . . 107.5(2) ?
    O6 C7 H7A . . 110.2 ?
    C8 C7 H7A . . 110.2 ?
    O6 C7 H7B . . 110.2 ?
    C8 C7 H7B . . 110.2 ?
    H7A C7 H7B . . 108.5 ?
    C7 C8 C9 . . 113.7(2) ?
    C7 C8 H8A . . 108.8 ?
    C9 C8 H8A . . 108.8 ?
    C7 C8 H8B . . 108.8 ?
    C9 C8 H8B . . 108.8 ?
    H8A C8 H8B . . 107.7 ?
    C8 C9 Si2 . . 115.46(19) ?
    C8 C9 H9A . . 108.4 ?
    Si2 C9 H9A . . 108.4 ?
    C8 C9 H9B . . 108.4 ?
    Si2 C9 H9B . . 108.4 ?
    H9A C9 H9B . . 107.5 ?
    Si2 C10 H10A . . 109.5 ?
    Si2 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    Si2 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    Si2 C11 H11A . . 109.5 ?
    Si2 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    Si2 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    Si2 C12 H12A . . 109.5 ?
    Si2 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    Si2 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    P2 C13 P1 . . 115.45(15) ?
    P2 C13 H13A . . 108.4 ?
    P1 C13 H13A . . 108.4 ?
    P2 C13 H13B . . 108.4 ?
    P1 C13 H13B . . 108.4 ?
    H13A C13 H13B . . 107.5 ?
    P1 O2 H2 . . 109.5 ?
    C1 O3 P1 . . 121.46(19) ?
    P2 O5 H5 . . 109.5 ?
    C7 O6 P2 . . 123.21(18) ?
    O1 P1 O2 . . 115.79(12) y
    O1 P1 O3 . . 113.16(12) y
    O2 P1 O3 . . 100.31(11) y
    O1 P1 C13 . . 111.17(13) y
    O2 P1 C13 . . 109.79(12) y
    O3 P1 C13 . . 105.72(12) y
    O4 P2 O5 . . 113.86(12) y
    O4 P2 O6 . . 116.29(12) y
    O5 P2 O6 . . 104.70(11) y
    O4 P2 C13 . . 111.41(12) y
    O5 P2 C13 . . 108.38(13) y
    O6 P2 C13 . . 101.16(13) y
    C5 Si1 C6 . . 110.22(15) ?
    C5 Si1 C4 . . 108.40(15) ?
    C6 Si1 C4 . . 109.39(16) ?
    C5 Si1 C3 . . 109.60(14) ?
    C6 Si1 C3 . . 109.63(13) ?
    C4 Si1 C3 . . 109.59(14) ?
    C9 Si2 C11 . . 108.58(15) ?
    C9 Si2 C12 . . 108.90(14) ?
    C11 Si2 C12 . . 109.31(16) ?
    C9 Si2 C10 . . 110.31(15) ?
    C11 Si2 C10 . . 110.35(16) ?
    C12 Si2 C10 . . 109.37(18) ?
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
    O2 H2 O4 2_565 0.82 1.78 2.518(3) 148
    O5 H5 O1 2_665 0.82 1.83 2.493(3) 137
