#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:39:23 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178879 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/08/4110867.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_4110867
loop_
_publ_author_name
'Rosa E. Bulo'
'Florian Allaart'
'Andreas W. Ehlers'
'Franciscus J. J. de Kanter'
'Marius Schakel'
'Martin Lutz'
'Anthony L. Spek'
'Koop Lammertsma'
_publ_contact_author_address
; Bijvoet Center for Biomolecular Research
  Dep. Crystal and Structural Chemistry
  Utrecht University
  Padualaan 8
  3584 CH Utrecht
  The Netherlands
;
_publ_contact_author_email       m.lutz@chem.uu.nl
_publ_contact_author_fax         '[+31] 30 2533940'
_publ_contact_author_name        'Martin Lutz'
_publ_contact_author_phone       '[+31] 30 2533902'
_publ_section_title
;
 Circumambulatory Rearrangement with Characteristics of a 2:1 Covalent
 Molecular Bevel Gear
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12169
_journal_page_last               12173
_journal_paper_doi               10.1021/ja0627895
_journal_volume                  128
_journal_year                    2006
_chemical_formula_moiety         'C14 H11 O5 P W'
_chemical_formula_sum            'C14 H11 O5 P W'
_chemical_formula_weight         474.05
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.442(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0373(11)
_cell_length_b                   13.4576(11)
_cell_length_c                   13.5480(11)
_cell_measurement_reflns_used    92
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.75
_cell_measurement_theta_min      3.84
_cell_volume                     1544.0(3)
_computing_cell_refinement       Dirax
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'EvalCCD, ABST, Sortav'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF-97 (Beurskens et al., 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            20279
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    7.601
_exptl_absorpt_correction_T_max  0.37
_exptl_absorpt_correction_T_min  0.17
_exptl_absorpt_correction_type   analytical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.039
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.606
_refine_diff_density_min         -1.081
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0177
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0225P)²+1.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0432
_refine_ls_wR_factor_ref         0.0448
_reflns_number_gt                3192
_reflns_number_total             3522
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja0627895si20060501_050610_2.cif
_cod_data_source_block           s2938a
_cod_original_cell_volume        1543.9(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4110867
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'
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_symmetry_multiplicity
_atom_site_calc_flag
W1 W 0.121059(12) 0.141200(7) 0.354496(8) 0.01687(5) Uani 1 1 d
P1 P 0.36519(8) 0.22926(5) 0.35407(5) 0.01718(13) Uani 1 1 d
O1 O 0.0537(3) 0.04941(18) 0.12672(17) 0.0379(5) Uani 1 1 d
O2 O 0.3355(3) -0.04607(17) 0.45339(18) 0.0383(5) Uani 1 1 d
O3 O 0.1555(3) 0.2402(2) 0.57346(18) 0.0483(7) Uani 1 1 d
O4 O -0.0801(3) 0.32815(19) 0.2413(2) 0.0422(6) Uani 1 1 d
O5 O -0.1686(3) 0.02475(18) 0.37402(19) 0.0396(6) Uani 1 1 d
C1 C 0.4940(4) 0.2774(2) 0.4834(2) 0.0277(6) Uani 1 1 d
C2 C 0.6613(4) 0.3018(3) 0.4920(3) 0.0353(7) Uani 1 1 d
C3 C 0.7101(4) 0.3523(2) 0.4236(3) 0.0365(8) Uani 1 1 d
C4 C 0.6209(4) 0.3937(2) 0.3208(3) 0.0320(7) Uani 1 1 d
C5 C 0.4668(4) 0.3949(2) 0.2659(3) 0.0283(6) Uani 1 1 d
C6 C 0.3354(3) 0.35609(19) 0.2988(2) 0.0217(6) Uani 1 1 d
C7 C 0.3303(4) 0.4140(2) 0.3927(3) 0.0290(6) Uani 1 1 d
C8 C 0.4098(4) 0.3749(2) 0.4855(3) 0.0344(8) Uani 1 1 d
C9 C 0.4856(4) 0.1612(2) 0.2955(3) 0.0293(7) Uani 1 1 d
C10 C 0.0811(3) 0.0826(2) 0.2084(2) 0.0242(6) Uani 1 1 d
C11 C 0.2595(3) 0.0219(2) 0.4200(2) 0.0246(6) Uani 1 1 d
C12 C 0.1470(4) 0.2037(2) 0.4960(2) 0.0282(6) Uani 1 1 d
C13 C -0.0100(3) 0.2611(2) 0.2832(2) 0.0254(6) Uani 1 1 d
C14 C -0.0650(3) 0.0677(2) 0.3643(2) 0.0257(6) Uani 1 1 d
H1 H 0.492(4) 0.230(2) 0.538(2) 0.025(8) Uiso 1 1 d
H2 H 0.741(5) 0.272(3) 0.557(3) 0.054(12) Uiso 1 1 d
H3 H 0.825(6) 0.364(3) 0.448(4) 0.063(14) Uiso 1 1 d
H4 H 0.688(4) 0.417(3) 0.291(3) 0.037(10) Uiso 1 1 d
H5 H 0.427(4) 0.424(3) 0.194(3) 0.047(11) Uiso 1 1 d
H6 H 0.237(4) 0.358(2) 0.241(3) 0.024(9) Uiso 1 1 d
H7 H 0.280(5) 0.477(3) 0.388(3) 0.052(11) Uiso 1 1 d
H8 H 0.422(4) 0.405(3) 0.550(3) 0.039(10) Uiso 1 1 d
H9A H 0.420(5) 0.142(3) 0.229(3) 0.041(11) Uiso 1 1 d
H9B H 0.567(5) 0.201(3) 0.287(3) 0.062(13) Uiso 1 1 d
H9C H 0.517(5) 0.101(3) 0.335(3) 0.049(11) Uiso 1 1 d
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'
W W -0.8490 6.8722 '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
C14 W1 C12 87.97(12)
C14 W1 C13 93.48(12)
C12 W1 C13 88.63(12)
C14 W1 C11 89.07(12)
C12 W1 C11 93.70(12)
C13 W1 C11 176.60(11)
C14 W1 C10 90.33(11)
C12 W1 C10 176.34(11)
C13 W1 C10 88.23(11)
C11 W1 C10 89.51(11)
C14 W1 P1 176.19(8)
C12 W1 P1 89.69(9)
C13 W1 P1 89.47(8)
C11 W1 P1 88.07(8)
C10 W1 P1 92.17(8)
C9 P1 C6 108.40(15)
C9 P1 C1 108.53(16)
C6 P1 C1 90.85(14)
C9 P1 W1 115.32(11)
C6 P1 W1 115.77(9)
C1 P1 W1 115.25(10)
C2 C1 C8 107.7(3)
C2 C1 P1 115.5(2)
C8 C1 P1 99.6(2)
C2 C1 H1 111.4(18)
C8 C1 H1 113.7(18)
P1 C1 H1 108.5(18)
C3 C2 C1 128.2(3)
C3 C2 H2 120(2)
C1 C2 H2 112(2)
C2 C3 C4 130.5(3)
C2 C3 H3 114(3)
C4 C3 H3 115(3)
C5 C4 C3 131.4(3)
C5 C4 H4 119(2)
C3 C4 H4 109(2)
C4 C5 C6 127.8(3)
C4 C5 H5 120(2)
C6 C5 H5 112(2)
C5 C6 C7 109.4(2)
C5 C6 P1 115.1(2)
C7 C6 P1 100.3(2)
C5 C6 H6 110(2)
C7 C6 H6 112.7(19)
P1 C6 H6 108.8(17)
C8 C7 C6 115.5(3)
C8 C7 H7 120(2)
C6 C7 H7 124(2)
C7 C8 C1 115.9(3)
C7 C8 H8 124(2)
C1 C8 H8 120(2)
P1 C9 H9A 107(2)
P1 C9 H9B 112(3)
H9A C9 H9B 107(4)
P1 C9 H9C 107(2)
H9A C9 H9C 106(3)
H9B C9 H9C 117(4)
O1 C10 W1 177.7(3)
O2 C11 W1 177.8(3)
O3 C12 W1 177.2(3)
O4 C13 W1 177.7(3)
O5 C14 W1 177.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
W1 C14 1.995(3)
W1 C12 2.030(3)
W1 C13 2.035(3)
W1 C11 2.039(3)
W1 C10 2.042(3)
W1 P1 2.5062(7)
P1 C9 1.804(3)
P1 C6 1.846(3)
P1 C1 1.850(3)
O1 C10 1.137(3)
O2 C11 1.138(4)
O3 C12 1.137(4)
O4 C13 1.134(4)
O5 C14 1.146(4)
C1 C2 1.512(4)
C1 C8 1.521(5)
C1 H1 0.98(3)
C2 C3 1.341(5)
C2 H2 1.01(4)
C3 C4 1.455(5)
C3 H3 0.99(5)
C4 C5 1.330(4)
C4 H4 0.90(4)
C5 C6 1.500(4)
C5 H5 0.99(4)
C6 C7 1.506(4)
C6 H6 0.96(3)
C7 C8 1.320(5)
C7 H7 0.96(4)
C8 H8 0.93(4)
C9 H9A 0.93(4)
C9 H9B 0.95(5)
C9 H9C 0.96(4)
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
C12 W1 P1 C9 144.84(16)
C13 W1 P1 C9 -126.53(15)
C11 W1 P1 C9 51.13(15)
C10 W1 P1 C9 -38.32(15)
C12 W1 P1 C6 -87.13(14)
C13 W1 P1 C6 1.50(13)
C11 W1 P1 C6 179.16(13)
C10 W1 P1 C6 89.71(13)
C12 W1 P1 C1 17.10(14)
C13 W1 P1 C1 105.74(14)
C11 W1 P1 C1 -76.61(14)
C10 W1 P1 C1 -166.05(14)
C9 P1 C1 C2 31.0(3)
C6 P1 C1 C2 -78.7(3)
W1 P1 C1 C2 162.1(2)
C9 P1 C1 C8 146.0(2)
C6 P1 C1 C8 36.2(2)
W1 P1 C1 C8 -82.96(19)
C8 C1 C2 C3 -64.2(5)
P1 C1 C2 C3 46.0(5)
C1 C2 C3 C4 -3.4(7)
C2 C3 C4 C5 1.1(7)
C3 C4 C5 C6 3.4(6)
C4 C5 C6 C7 63.3(4)
C4 C5 C6 P1 -48.6(4)
C9 P1 C6 C5 -29.3(3)
C1 P1 C6 C5 80.6(2)
W1 P1 C6 C5 -160.68(19)
C9 P1 C6 C7 -146.5(2)
C1 P1 C6 C7 -36.6(2)
W1 P1 C6 C7 82.10(19)
C5 C6 C7 C8 -93.6(3)
P1 C6 C7 C8 27.7(3)
C6 C7 C8 C1 -0.2(4)
C2 C1 C8 C7 93.4(3)
P1 C1 C8 C7 -27.4(3)
