#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:21:51 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179661 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/14/4511418.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4511418
loop_
_publ_author_name
'Gagnon, Kevin J.'
'Teat, Simon J.'
'Beal, Zachary J.'
'Embry, Alyssa M.'
'Strayer, Megan E.'
'Clearfield, Abraham'
_publ_section_title
;
 Isoreticular Investigation into the Formation of Four New Zinc
 Alkylbisphosphonate Families
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3612
_journal_paper_doi               10.1021/cg500568e
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C12 H26 O12 P4 Zn3'
_chemical_formula_weight         682.32
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                100.409(2)
_cell_angle_beta                 104.701(2)
_cell_angle_gamma                90.945(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6850(13)
_cell_length_b                   9.9739(15)
_cell_length_c                   12.8831(19)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.193
_cell_measurement_theta_min      2.7935
_cell_volume                     1059.4(3)
_computing_cell_refinement       'SAINT V8.34A Bruker-AXS, Madison WI'
_computing_data_collection       'Bruker APEX-II Bruker-AXS, Madison WI'
_computing_data_reduction        'SAINT V8.34A Bruker-AXS, Madison WI'
_computing_molecular_graphics
;
Bruker SHELXTL Bruker-AXS, Madison WI
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
and local programs
;
_computing_publication_material  'Bruker SHELXTL Bruker-AXS, Madison WI'
_computing_structure_refinement  'SHELXL-2013/4 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT 2014/1 Bruker-AXS, Madison WI'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       '/w scans with narrow frames'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7749
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10669
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        27.706
_diffrn_reflns_theta_max         33.607
_diffrn_reflns_theta_min         2.793
_diffrn_source
;
Advanced Light Source, station 11.3.1
;
_exptl_absorpt_coefficient_mu    4.714
_exptl_absorpt_correction_T_max  0.704
_exptl_absorpt_correction_T_min  0.540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS-2012/1 - Bruker AXS, Madison WI'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.915
_refine_diff_density_min         -0.970
_refine_diff_density_rms         0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         6449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0629P)²+0.1788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1017
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5524
_reflns_number_total             6449
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg500568e_si_002.cif
_cod_data_source_block           zal6
_cod_depositor_comments
'Adding full bibliography for 4511411--4511421.cif.'
_cod_database_code               4511418
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.332
_shelx_estimated_absorpt_t_max   0.704
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Zn01 Zn 0.35382(3) 0.44854(3) 0.57583(2) 0.01073(7) Uani 1 1 d . .
Zn02 Zn -0.24604(3) 0.25532(3) 0.49562(2) 0.01143(8) Uani 1 1 d . .
Zn03 Zn 0.29850(3) 0.04432(3) 0.44900(2) 0.01214(8) Uani 1 1 d . .
P2 P 0.54489(7) 0.21866(6) -0.34794(5) 0.00973(12) Uani 1 1 d . .
P3 P 0.03414(7) 0.47031(7) 0.65856(5) 0.01185(12) Uani 1 1 d . .
P1 P 0.41102(7) 0.28506(7) 0.36142(5) 0.00973(12) Uani 1 1 d . .
P4 P -0.08768(7) 0.02999(7) 0.34738(6) 0.01232(13) Uani 1 1 d . .
O1 O 0.2973(2) 0.35863(19) 0.42228(15) 0.0119(3) Uani 1 1 d . .
O5 O 0.6690(2) 0.15353(18) -0.40736(15) 0.0111(3) Uani 1 1 d . .
O8 O 0.2044(2) 0.4423(2) 0.66123(15) 0.0143(4) Uani 1 1 d . .
O2 O 0.5830(2) 0.35460(18) 0.41220(15) 0.0112(3) Uani 1 1 d . .
O3 O 0.4142(2) 0.13423(18) 0.36424(15) 0.0125(3) Uani 1 1 d . .
O6 O 0.3790(2) 0.1496(2) -0.40295(15) 0.0134(3) Uani 1 1 d . .
O10 O 0.0826(2) 0.0821(2) 0.39515(17) 0.0172(4) Uani 1 1 d . .
O11 O -0.2030(2) 0.0934(2) 0.40864(18) 0.0186(4) Uani 1 1 d . .
O4 O 0.5483(2) 0.37084(19) -0.34702(15) 0.0125(3) Uani 1 1 d . .
O7 O -0.0900(2) 0.3999(2) 0.55780(16) 0.0160(4) Uani 1 1 d . .
O12 O -0.1011(2) -0.1296(2) 0.34157(17) 0.0172(4) Uani 1 1 d . .
H12 H -0.1868 -0.1517 0.3549 0.026 Uiso 1 1 calc R U
O9 O 0.0195(2) 0.6294(2) 0.67017(16) 0.0158(4) Uani 1 1 d . .
H9 H -0.0752 0.6452 0.6420 0.024 Uiso 1 1 calc R U
C6 C 0.6030(3) 0.1885(3) -0.2111(2) 0.0130(4) Uani 1 1 d . .
H6A H 0.5998 0.0887 -0.2133 0.016 Uiso 1 1 calc R U
H6B H 0.7144 0.2254 -0.1768 0.016 Uiso 1 1 calc R U
C5 C 0.4966(3) 0.2532(3) -0.1404(2) 0.0156(5) Uani 1 1 d . .
H5A H 0.3839 0.2235 -0.1783 0.019 Uiso 1 1 calc R U
H5B H 0.5084 0.3538 -0.1318 0.019 Uiso 1 1 calc R U
C1 C 0.3535(3) 0.3080(3) 0.2225(2) 0.0137(4) Uani 1 1 d . .
H1A H 0.2446 0.2655 0.1874 0.016 Uiso 1 1 calc R U
H1B H 0.3505 0.4070 0.2214 0.016 Uiso 1 1 calc R U
C7 C -0.0060(3) 0.4272(3) 0.7789(2) 0.0152(5) Uani 1 1 d . .
H7A H -0.1160 0.4497 0.7805 0.018 Uiso 1 1 calc R U
H7B H 0.0006 0.3276 0.7754 0.018 Uiso 1 1 calc R U
C3 C 0.4265(3) 0.2769(3) 0.0410(2) 0.0165(5) Uani 1 1 d . .
H3A H 0.4319 0.3772 0.0463 0.020 Uiso 1 1 calc R U
H3B H 0.3154 0.2418 0.0030 0.020 Uiso 1 1 calc R U
C2 C 0.4672(3) 0.2457(3) 0.1558(2) 0.0164(5) Uani 1 1 d . .
H2A H 0.5778 0.2818 0.1944 0.020 Uiso 1 1 calc R U
H2B H 0.4625 0.1454 0.1508 0.020 Uiso 1 1 calc R U
C12 C -0.1441(3) 0.0536(3) 0.2086(2) 0.0173(5) Uani 1 1 d . .
H12A H -0.2521 0.0096 0.1725 0.021 Uiso 1 1 calc R U
H12B H -0.1486 0.1525 0.2076 0.021 Uiso 1 1 calc R U
C4 C 0.5365(3) 0.2152(3) -0.0271(2) 0.0160(5) Uani 1 1 d . .
H4A H 0.5277 0.1145 -0.0355 0.019 Uiso 1 1 calc R U
H4B H 0.6481 0.2474 0.0118 0.019 Uiso 1 1 calc R U
C8 C 0.1107(3) 0.5029(3) 0.8847(2) 0.0203(5) Uani 1 1 d . .
H8A H 0.1070 0.6024 0.8864 0.024 Uiso 1 1 calc R U
H8B H 0.2202 0.4778 0.8837 0.024 Uiso 1 1 calc R U
C10 C -0.0598(4) 0.0285(3) 0.0309(2) 0.0222(6) Uani 1 1 d . .
H10A H -0.1684 -0.0084 -0.0118 0.027 Uiso 1 1 calc R U
H10B H -0.0562 0.1291 0.0379 0.027 Uiso 1 1 calc R U
C11 C -0.0272(4) -0.0067(3) 0.1442(2) 0.0211(5) Uani 1 1 d . .
H11A H 0.0827 0.0277 0.1859 0.025 Uiso 1 1 calc R U
H11B H -0.0337 -0.1073 0.1369 0.025 Uiso 1 1 calc R U
C9 C 0.0762(3) 0.4721(3) 0.9896(2) 0.0213(6) Uani 1 1 d . .
H9A H 0.0698 0.3719 0.9848 0.026 Uiso 1 1 calc R U
H9B H 0.1665 0.5114 1.0526 0.026 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020 'Calculated using XDISP in WinGX (Farrugia, 1999)'
H H 0.0000 0.0000 'Calculated using XDISP in WinGX (Farrugia, 1999)'
O O 0.0132 0.0074 'Calculated using XDISP in WinGX (Farrugia, 1999)'
P P 0.1183 0.1134 'Calculated using XDISP in WinGX (Farrugia, 1999)'
Zn Zn 0.2282 1.6718 'Calculated using XDISP in WinGX (Farrugia, 1999)'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O8 Zn01 O1 119.97(8) . .
O8 Zn01 O4 106.05(8) . 1_556
O1 Zn01 O4 108.53(8) . 1_556
O8 Zn01 O2 106.97(8) . 2_666
O1 Zn01 O2 109.31(8) . 2_666
O4 Zn01 O2 105.02(7) 1_556 2_666
O7 Zn02 O11 121.52(8) . .
O7 Zn02 O2 99.61(8) . 1_455
O11 Zn02 O2 112.29(9) . 1_455
O7 Zn02 O5 119.91(8) . 1_456
O11 Zn02 O5 93.31(8) . 1_456
O2 Zn02 O5 110.72(7) 1_455 1_456
O10 Zn03 O6 108.55(8) . 1_556
O10 Zn03 O3 104.29(8) . .
O6 Zn03 O3 102.93(8) 1_556 .
O10 Zn03 O5 111.42(8) . 2_655
O6 Zn03 O5 123.40(8) 1_556 2_655
O3 Zn03 O5 104.12(7) . 2_655
O4 P2 O6 111.68(11) . .
O4 P2 O5 109.18(10) . .
O6 P2 O5 110.45(10) . .
O4 P2 C6 110.10(12) . .
O6 P2 C6 108.26(11) . .
O5 P2 C6 107.06(11) . .
O8 P3 O7 116.05(11) . .
O8 P3 O9 107.76(11) . .
O7 P3 O9 108.47(11) . .
O8 P3 C7 107.96(11) . .
O7 P3 C7 110.37(12) . .
O9 P3 C7 105.73(12) . .
O3 P1 O1 113.32(10) . .
O3 P1 O2 109.45(10) . .
O1 P1 O2 109.00(10) . .
O3 P1 C1 109.57(12) . .
O1 P1 C1 108.69(11) . .
O2 P1 C1 106.59(11) . .
O10 P4 O11 115.18(12) . .
O10 P4 O12 109.17(11) . .
O11 P4 O12 107.97(11) . .
O10 P4 C12 107.74(12) . .
O11 P4 C12 110.60(12) . .
O12 P4 C12 105.78(13) . .
P1 O1 Zn01 125.69(11) . .
P2 O5 Zn03 127.70(10) . 2_655
P2 O5 Zn02 119.88(10) . 1_654
Zn03 O5 Zn02 108.36(8) 2_655 1_654
P3 O8 Zn01 140.53(12) . .
P1 O2 Zn02 120.29(10) . 1_655
P1 O2 Zn01 125.78(10) . 2_666
Zn02 O2 Zn01 113.15(8) 1_655 2_666
P1 O3 Zn03 123.41(11) . .
P2 O6 Zn03 128.56(11) . 1_554
P4 O10 Zn03 148.66(14) . .
P4 O11 Zn02 144.21(13) . .
P2 O4 Zn01 118.72(11) . 1_554
P3 O7 Zn02 146.66(13) . .
P4 O12 H12 109.5 . .
P3 O9 H9 109.5 . .
C5 C6 P2 113.18(17) . .
C5 C6 H6A 108.9 . .
P2 C6 H6A 108.9 . .
C5 C6 H6B 108.9 . .
P2 C6 H6B 108.9 . .
H6A C6 H6B 107.8 . .
C6 C5 C4 112.9(2) . .
C6 C5 H5A 109.0 . .
C4 C5 H5A 109.0 . .
C6 C5 H5B 109.0 . .
C4 C5 H5B 109.0 . .
H5A C5 H5B 107.8 . .
C2 C1 P1 112.85(17) . .
C2 C1 H1A 109.0 . .
P1 C1 H1A 109.0 . .
C2 C1 H1B 109.0 . .
P1 C1 H1B 109.0 . .
H1A C1 H1B 107.8 . .
C8 C7 P3 112.70(19) . .
C8 C7 H7A 109.1 . .
P3 C7 H7A 109.1 . .
C8 C7 H7B 109.1 . .
P3 C7 H7B 109.1 . .
H7A C7 H7B 107.8 . .
C2 C3 C4 113.5(2) . .
C2 C3 H3A 108.9 . .
C4 C3 H3A 108.9 . .
C2 C3 H3B 108.9 . .
C4 C3 H3B 108.9 . .
H3A C3 H3B 107.7 . .
C3 C2 C1 112.5(2) . .
C3 C2 H2A 109.1 . .
C1 C2 H2A 109.1 . .
C3 C2 H2B 109.1 . .
C1 C2 H2B 109.1 . .
H2A C2 H2B 107.8 . .
C11 C12 P4 112.14(19) . .
C11 C12 H12A 109.2 . .
P4 C12 H12A 109.2 . .
C11 C12 H12B 109.2 . .
P4 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
C3 C4 C5 112.3(2) . .
C3 C4 H4A 109.1 . .
C5 C4 H4A 109.1 . .
C3 C4 H4B 109.1 . .
C5 C4 H4B 109.1 . .
H4A C4 H4B 107.9 . .
C7 C8 C9 114.1(2) . .
C7 C8 H8A 108.7 . .
C9 C8 H8A 108.7 . .
C7 C8 H8B 108.7 . .
C9 C8 H8B 108.7 . .
H8A C8 H8B 107.6 . .
C10 C10 C11 112.6(3) 2 .
C10 C10 H10A 109.1 2 .
C11 C10 H10A 109.1 . .
C10 C10 H10B 109.1 2 .
C11 C10 H10B 109.1 . .
H10A C10 H10B 107.8 . .
C10 C11 C12 113.1(2) . .
C10 C11 H11A 109.0 . .
C12 C11 H11A 109.0 . .
C10 C11 H11B 109.0 . .
C12 C11 H11B 109.0 . .
H11A C11 H11B 107.8 . .
C9 C9 C8 113.8(3) 2_567 .
C9 C9 H9A 108.8 2_567 .
C8 C9 H9A 108.8 . .
C9 C9 H9B 108.8 2_567 .
C8 C9 H9B 108.8 . .
H9A C9 H9B 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn01 O8 1.9089(18) .
Zn01 O1 1.9519(19) .
Zn01 O4 1.9774(18) 1_556
Zn01 O2 1.9982(18) 2_666
Zn02 O7 1.8778(19) .
Zn02 O11 1.893(2) .
Zn02 O2 1.9910(18) 1_455
Zn02 O5 2.0100(17) 1_456
Zn03 O10 1.8969(19) .
Zn03 O6 1.9508(19) 1_556
Zn03 O3 1.9713(18) .
Zn03 O5 1.9936(18) 2_655
P2 O4 1.5155(19) .
P2 O6 1.5248(19) .
P2 O5 1.5593(18) .
P2 C6 1.789(3) .
P3 O8 1.5026(18) .
P3 O7 1.509(2) .
P3 O9 1.577(2) .
P3 C7 1.794(3) .
P1 O3 1.5119(19) .
P1 O1 1.5292(18) .
P1 O2 1.5636(18) .
P1 C1 1.790(3) .
P4 O10 1.4941(19) .
P4 O11 1.506(2) .
P4 O12 1.581(2) .
P4 C12 1.790(3) .
O12 H12 0.8400 .
O9 H9 0.8400 .
C6 C5 1.528(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C5 C4 1.530(4) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C1 C2 1.535(3) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C7 C8 1.535(4) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C3 C2 1.521(4) .
C3 C4 1.521(4) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C12 C11 1.532(4) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C8 C9 1.537(4) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C10 C10 1.519(6) 2
C10 C11 1.522(4) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C9 C9 1.512(5) 2_567
C9 H9A 0.9900 .
C9 H9B 0.9900 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 O6 0.84 1.92 2.739(3) 164.1 2
O9 H9 O1 0.84 1.89 2.720(3) 167.9 2_566
