#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/46/2204607.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2204607
loop_
_publ_author_name
'McLauchlan, Craig C.'
'Stepinski, Dominique C.'
'Herlinger, Albert W.'
_publ_section_title
;
 Bis[3-(trimethylsilyl)propyl] methylenebisphosphonate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2232
_journal_page_last               o2234
_journal_paper_doi               10.1107/S1600536804028028
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C13 H34 O6 P2 Si2'
_chemical_formula_moiety         'C13 H34 O6 P2 Si2'
_chemical_formula_sum            'C13 H34 O6 P2 Si2'
_chemical_formula_weight         404.52
_chemical_melting_point          313.0(10)
_chemical_name_systematic
;
Bis[3-(trimethylsilyl)propyl] methylenebisphosphonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.640(10)
_cell_angle_beta                 100.250(10)
_cell_angle_gamma                106.23(2)
_cell_formula_units_Z            2
_cell_length_a                   6.534(2)
_cell_length_b                   11.130(2)
_cell_length_c                   16.325(2)
_cell_measurement_reflns_used    3959
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.4232
_cell_measurement_theta_min      1.7559
_cell_volume                     1086.6(4)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2004)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2004)
;
_computing_data_reduction
;
CrysAlis RED
;
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur3 diffractometer equipped with a CCD detector
;
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10850
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         4.20
_diffrn_standards_decay_%        <1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  0.98329
_exptl_absorpt_correction_T_min  0.88844
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(Clark & Reid, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.36465
_exptl_crystal_size_mid          0.13321
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.998
_refine_diff_density_min         -0.573
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0607
_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/[σ²(Fo²)+(0.1P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.1780
_reflns_number_gt                3556
_reflns_number_total             4971
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            br6168.cif
_cod_data_source_block           I
_cod_database_code               2204607
_cod_database_fobs_code          2204607
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_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
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_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_bond_atom_site_label_1
_geom_bond_atom_site_label_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_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
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8448066
