##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2006-12-12
_journal_date_accepted     2006-12-21
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2007
_journal_volume     63
_journal_issue      2
_journal_page_first     o132
_journal_page_last     o134
_journal_paper_category     FO
_journal_coeditor_code     SQ3056
_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] ethylenebisphosphonate, H₂DTMSP[EBP]
;
loop_
    _publ_author_name
    _publ_author_address
    'McLauchlan, Craig C.'
;
Department of Chemistry
Illinois State University
Campus Box 4160
Normal
IL 61790-4160
USA
;
    'Ziegler, Amanda J.'
;
Department of Chemistry
Loyola University Chicago
Chicago
IL 60626
USA
;
    'Sosnowski, Cyndi R.'
;
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     SHELXL97
_chemical_name_systematic
;
Bis[3-(trimethylsilyl)propyl] ethylenebisphosphonate
;
_chemical_name_common
;
P,P'-di[3-(trimethylsilyl)-1-propyl]
ethylenebisphosphonic acid
;
_chemical_formula_moiety     'C14 H36 O6 P2 Si2'
_chemical_formula_sum     'C14 H36 O6 P2 Si2'
_chemical_formula_iupac     'C14 H36 O6 P2 Si2'
_chemical_formula_weight     418.55
_chemical_melting_point     91.0(10)
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    '-x-1/2, y-1/2, z'
    'x, -y-1/2, z-1/2'
_cell_length_a     7.6865(3)
_cell_length_b     11.0294(8)
_cell_length_c     26.8912(13)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2279.8(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6010
_cell_measurement_theta_min     3.7833
_cell_measurement_theta_max     28.4975
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.3874
_exptl_crystal_size_mid     0.2385
_exptl_crystal_size_min     0.2140
_exptl_crystal_density_diffrn     1.219
_exptl_crystal_density_meas     .
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     904
_exptl_absorpt_coefficient_mu     0.319
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details
;
Analytical numerical absorption correction using a multifaceted crystal
model based on expressions derived by Clark & Reid (1995)
;
_exptl_absorpt_correction_T_min     0.923
_exptl_absorpt_correction_T_max     0.948
_exptl_special_details
;
 ?
;
_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 Xcalibur3 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     15.9890
_diffrn_reflns_number     10013
_diffrn_reflns_av_R_equivalents     0.0255
_diffrn_reflns_av_sigmaI/netI     0.0239
_diffrn_reflns_theta_min     3.95
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -32
_diffrn_reflns_limit_l_max     34
_diffrn_standards_number     0
_diffrn_standards_interval_count     '50 frames'
_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     2598
_reflns_number_gt     2091
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0449
_refine_ls_R_factor_gt     0.0327
_refine_ls_wR_factor_gt     0.0801
_refine_ls_wR_factor_ref     0.0869
_refine_ls_goodness_of_fit_ref     1.051
_refine_ls_restrained_S_all     1.050
_refine_ls_number_reflns     2598
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0448P)²+0.9918P] 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     0.403
_refine_diff_density_min     -0.283
_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'
    'Si' 'Si' 0.0817 0.0704
                         '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     'CrysAlis CCD (Oxford, 2006)'
_computing_cell_refinement     'CrysAlis RED (Oxford, 2006)'
_computing_data_reduction     'CrysAlis RED'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXL97'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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
    C C1 0.6663(2) 0.59694(16) 0.07682(6) 0.0228(4) Uani d . 1 . .
    H H1A 0.6451 0.5477 0.0476 0.027 Uiso calc R 1 . .
    H H1B 0.5980 0.6706 0.0740 0.027 Uiso calc R 1 . .
    C C2 0.6139(2) 0.52865(16) 0.12270(6) 0.0230(4) Uani d . 1 . .
    H H2A 0.6298 0.5800 0.1516 0.028 Uiso calc R 1 . .
    H H2B 0.6879 0.4580 0.1265 0.028 Uiso calc R 1 . .
    C C3 0.4235(2) 0.48836(15) 0.11960(6) 0.0207(3) Uani d . 1 . .
    H H3A 0.4096 0.4374 0.0905 0.025 Uiso calc R 1 . .
    H H3B 0.3515 0.5597 0.1148 0.025 Uiso calc R 1 . .
    C C4 0.3418(2) 0.50535(16) 0.23040(6) 0.0275(4) Uani d U 1 . .
    H H4A 0.2966 0.4625 0.2587 0.041 Uiso calc R 1 . .
    H H4B 0.2705 0.5750 0.2239 0.041 Uiso calc R 1 . .
    H H4C 0.4587 0.5310 0.2372 0.041 Uiso calc R 1 . .
    C C5 0.4840(3) 0.27110(16) 0.18826(7) 0.0286(4) Uani d U 1 . .
    H H5A 0.6027 0.2977 0.1902 0.043 Uiso calc R 1 . .
    H H5B 0.4725 0.2125 0.1621 0.043 Uiso calc R 1 . .
    H H5C 0.4505 0.2349 0.2193 0.043 Uiso calc R 1 . .
    C C6 0.1140(2) 0.35234(18) 0.16084(7) 0.0301(4) Uani d U 1 . .
    H H6A 0.1149 0.3023 0.1316 0.045 Uiso calc R 1 . .
    H H6B 0.0413 0.4218 0.1552 0.045 Uiso calc R 1 . .
    H H6C 0.0693 0.3067 0.1884 0.045 Uiso calc R 1 . .
    C C7 0.9617(2) 0.55842(14) -0.01105(5) 0.0178(3) Uani d . 1 . .
    H H7A 0.8467 0.5412 -0.0241 0.021 Uiso calc R 1 . .
    H H7B 1.0341 0.5847 -0.0386 0.021 Uiso calc R 1 . .
    O O1 0.85763(14) 0.78640(10) 0.01125(4) 0.0218(3) Uani d . 1 . .
    O O2 1.12876(14) 0.70338(11) 0.05460(4) 0.0207(3) Uani d . 1 . .
    H H2 1.1988 0.7091 0.0317 0.031 Uiso calc R 1 . .
    O O3 0.85071(14) 0.62689(10) 0.08024(4) 0.0197(3) Uani d . 1 . .
    Si Si1 0.34062(6) 0.40350(4) 0.175058(16) 0.01931(13) Uani d U 1 . .
    P P1 0.94606(5) 0.67886(4) 0.033276(15) 0.01598(12) Uani 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
    C1 0.0122(7) 0.0296(8) 0.0267(8) -0.0002(7) 0.0004(6) 0.0032(7)
    C2 0.0190(8) 0.0269(8) 0.0232(8) -0.0020(7) -0.0008(7) 0.0034(7)
    C3 0.0166(8) 0.0223(8) 0.0232(8) -0.0006(6) -0.0007(6) 0.0022(7)
    C4 0.0214(9) 0.0302(9) 0.0310(9) -0.0001(7) -0.0003(7) -0.0047(7)
    C5 0.0339(10) 0.0248(9) 0.0270(9) 0.0032(8) -0.0014(8) 0.0033(7)
    C6 0.0237(9) 0.0347(10) 0.0320(9) -0.0095(8) 0.0001(8) -0.0020(8)
    C7 0.0163(8) 0.0207(8) 0.0166(7) -0.0003(6) -0.0015(6) -0.0008(6)
    O1 0.0170(6) 0.0204(5) 0.0279(6) 0.0013(5) -0.0014(5) 0.0008(5)
    O2 0.0136(5) 0.0267(6) 0.0217(6) -0.0016(5) -0.0013(5) -0.0022(5)
    O3 0.0134(5) 0.0270(6) 0.0188(5) -0.0015(5) 0.0011(4) 0.0002(5)
    Si1 0.0166(2) 0.0202(2) 0.0212(2) -0.00173(18) 0.00024(18) 0.00063(18)
    P1 0.0123(2) 0.0181(2) 0.0175(2) -0.00018(15) -0.00055(15) -0.00101(15)
_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 . 1.4587(18) ?
    C1 C2 . 1.500(2) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 C3 . 1.532(2) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 Si1 . 1.8722(16) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 Si1 . 1.8645(17) ?
    C4 H4A . 0.9600 ?
    C4 H4B . 0.9600 ?
    C4 H4C . 0.9600 ?
    C5 Si1 . 1.8635(18) ?
    C5 H5A . 0.9600 ?
    C5 H5B . 0.9600 ?
    C5 H5C . 0.9600 ?
    C6 Si1 . 1.8708(18) ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C7 C7 5_765 1.537(3) ?
    C7 P1 . 1.7888(15) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    O1 P1 . 1.4898(12) y
    O2 P1 . 1.5407(11) y
    O2 H2 . 0.8200 ?
    O3 P1 . 1.5687(11) 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 . . 108.80(13) ?
    O3 C1 H1A . . 109.9 ?
    C2 C1 H1A . . 109.9 ?
    O3 C1 H1B . . 109.9 ?
    C2 C1 H1B . . 109.9 ?
    H1A C1 H1B . . 108.3 ?
    C1 C2 C3 . . 110.92(13) ?
    C1 C2 H2A . . 109.5 ?
    C3 C2 H2A . . 109.5 ?
    C1 C2 H2B . . 109.5 ?
    C3 C2 H2B . . 109.5 ?
    H2A C2 H2B . . 108.0 ?
    C2 C3 Si1 . . 115.26(11) ?
    C2 C3 H3A . . 108.5 ?
    Si1 C3 H3A . . 108.5 ?
    C2 C3 H3B . . 108.5 ?
    Si1 C3 H3B . . 108.5 ?
    H3A C3 H3B . . 107.5 ?
    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 ?
    C7 C7 P1 5_765 . 113.00(14) ?
    C7 C7 H7A 5_765 . 109.0 ?
    P1 C7 H7A . . 109.0 ?
    C7 C7 H7B 5_765 . 109.0 ?
    P1 C7 H7B . . 109.0 ?
    H7A C7 H7B . . 107.8 ?
    P1 O2 H2 . . 109.5 ?
    C1 O3 P1 . . 119.08(10) ?
    C5 Si1 C4 . . 108.50(8) ?
    C5 Si1 C6 . . 110.68(9) ?
    C4 Si1 C6 . . 110.44(8) ?
    C5 Si1 C3 . . 110.02(8) ?
    C4 Si1 C3 . . 109.45(8) ?
    C6 Si1 C3 . . 107.74(8) ?
    O1 P1 O2 . . 115.09(7) y
    O1 P1 O3 . . 113.44(7) y
    O2 P1 O3 . . 100.98(6) y
    O1 P1 C7 . . 110.91(7) y
    O2 P1 C7 . . 108.49(7) y
    O3 P1 C7 . . 107.25(7) y
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
    O3 C1 C2 C3 . . . . -176.65(13) ?
    C1 C2 C3 Si1 . . . . -179.29(12) ?
    C2 C1 O3 P1 . . . . 169.72(11) ?
    C2 C3 Si1 C5 . . . . -54.44(14) ?
    C2 C3 Si1 C4 . . . . 64.69(14) ?
    C2 C3 Si1 C6 . . . . -175.19(12) ?
    C1 O3 P1 O1 . . . . 53.09(13) ?
    C1 O3 P1 O2 . . . . 176.79(11) ?
    C1 O3 P1 C7 . . . . -69.73(12) y
    C7 C7 P1 O1 5_765 . . . -175.25(14) ?
    C7 C7 P1 O2 5_765 . . . 57.42(17) ?
    C7 C7 P1 O3 5_765 . . . -50.88(17) y
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 O1 3_565 0.82 1.68 2.4986(16) 174.0
