#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/60/1506047.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_1506047
loop_
_publ_author_name
'Thornton, Paul D.'
'Burnell, D. Jean'
_publ_section_title
;
 A Pauson-Khand and ring-expansion approach to the aquariane ring system.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3195
_journal_page_last               3198
_journal_paper_doi               10.1021/ol0609715
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C20 H32 O3 Si'
_chemical_formula_weight         348.55
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.2128(10)
_cell_length_b                   14.5819(14)
_cell_length_c                   26.706(3)
_cell_measurement_reflns_used    6676
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.51
_cell_volume                     3977.1(7)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'teXsan for Windows (MSC, 1997)'
_computing_publication_material  'teXsan for Windows (MSC, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            29937
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         1.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.9602
_exptl_absorpt_correction_T_min  0.9356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0564
_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)+(0.0951P)²+3.2690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1683
_reflns_number_gt                3420
_reflns_number_total             4083
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0609715si20060423_101157.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1506047
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
Si Si 0.19464(6) 0.11112(5) 0.07999(2) 0.0391(2) Uani 1 1 d
O1 O 0.31812(13) 0.14863(10) 0.11319(5) 0.0283(3) Uani 1 1 d
O2 O 0.64622(15) 0.22768(11) 0.20644(6) 0.0329(4) Uani 1 1 d
O3 O 0.72695(19) -0.12136(12) 0.15647(8) 0.0511(5) Uani 1 1 d
C1 C 0.31876(18) 0.16968(13) 0.16537(7) 0.0235(4) Uani 1 1 d
C2 C 0.3245(2) 0.27338(14) 0.17195(8) 0.0300(4) Uani 1 1 d
C3 C 0.4654(2) 0.29749(13) 0.15753(9) 0.0308(5) Uani 1 1 d
C4 C 0.54940(18) 0.21095(12) 0.16869(7) 0.0227(4) Uani 1 1 d
C5 C 0.6171(2) 0.17630(14) 0.12075(8) 0.0273(4) Uani 1 1 d
C6 C 0.6874(2) 0.08422(15) 0.12644(9) 0.0336(5) Uani 1 1 d
C7 C 0.6006(2) 0.01806(13) 0.15364(7) 0.0265(4) Uani 1 1 d
C8 C 0.49194(18) 0.04367(12) 0.17704(7) 0.0222(4) Uani 1 1 d
C9 C 0.44963(17) 0.13896(12) 0.18871(7) 0.0208(4) Uani 1 1 d
C10 C 0.4340(2) 0.13137(14) 0.24689(7) 0.0289(4) Uani 1 1 d
C11 C 0.4527(3) 0.02999(17) 0.26123(9) 0.0551(8) Uani 1 1 d
C12 C 0.4373(2) -0.02553(14) 0.21258(8) 0.0329(5) Uani 1 1 d
C13 C 0.5259(3) -0.10855(15) 0.20517(10) 0.0407(6) Uani 1 1 d
C14 C 0.6308(2) -0.07695(14) 0.16860(8) 0.0330(5) Uani 1 1 d
C15 C 0.2397(2) 0.13558(18) 0.01359(8) 0.0422(6) Uani 1 1 d
C16 C 0.2606(4) 0.2381(3) 0.00751(12) 0.0848(13) Uani 1 1 d
C17 C 0.1313(3) 0.1031(2) -0.02214(11) 0.0517(7) Uani 1 1 d
C18 C 0.3653(4) 0.0853(4) 0.00005(15) 0.1048(17) Uani 1 1 d
C19 C 0.1743(6) -0.0118(3) 0.09271(19) 0.142(3) Uani 1 1 d
C20 C 0.0423(3) 0.1708(4) 0.09833(14) 0.1064(18) Uani 1 1 d
H1 H 0.244(2) 0.1419(15) 0.1829(9) 0.028 Uiso 1 1 d
H2 H 0.260(3) 0.3049(18) 0.1536(9) 0.036 Uiso 1 1 d
H3 H 0.305(2) 0.2904(17) 0.2079(10) 0.036 Uiso 1 1 d
H4 H 0.476(2) 0.3120(17) 0.1214(10) 0.037 Uiso 1 1 d
H5 H 0.499(3) 0.3466(18) 0.1767(9) 0.037 Uiso 1 1 d
H6 H 0.551(2) 0.1686(16) 0.0951(9) 0.033 Uiso 1 1 d
H7 H 0.681(2) 0.2212(17) 0.1120(9) 0.033 Uiso 1 1 d
H8 H 0.714(2) 0.0609(18) 0.0956(10) 0.040 Uiso 1 1 d
H9 H 0.773(3) 0.0926(18) 0.1444(10) 0.040 Uiso 1 1 d
H10 H 0.499(3) 0.1660(17) 0.2654(9) 0.035 Uiso 1 1 d
H11 H 0.356(3) 0.1523(16) 0.2570(10) 0.035 Uiso 1 1 d
H12 H 0.5385 0.0210 0.2750 0.067 Uiso 1 1 d
H13 H 0.3896 0.0119 0.2853 0.067 Uiso 1 1 d
H14 H 0.350(3) -0.0383(18) 0.2057(10) 0.040 Uiso 1 1 d
H15 H 0.571(3) -0.1250(18) 0.2372(11) 0.049 Uiso 1 1 d
H16 H 0.483(3) -0.1624(19) 0.1882(11) 0.049 Uiso 1 1 d
H17 H 0.2685 0.2661 0.0392 0.100 Uiso 1 1 d
H18 H 0.3392 0.2484 -0.0112 0.100 Uiso 1 1 d
H19 H 0.1890 0.2640 -0.0102 0.100 Uiso 1 1 d
H20 H 0.052(3) 0.132(2) -0.0150(12) 0.061 Uiso 1 1 d
H21 H 0.152(3) 0.112(2) -0.0540(14) 0.061 Uiso 1 1 d
H22 H 0.115(3) 0.038(2) -0.0190(12) 0.061 Uiso 1 1 d
H23 H 0.4079 0.0657 0.0302 0.130 Uiso 1 1 d
H24 H 0.3443 0.0320 -0.0192 0.130 Uiso 1 1 d
H25 H 0.4212 0.1237 -0.0182 0.130 Uiso 1 1 d
H26 H 0.1711 -0.0218 0.1278 0.168 Uiso 1 1 d
H27 H 0.0952 -0.0329 0.0778 0.168 Uiso 1 1 d
H28 H 0.2461 -0.0448 0.0788 0.168 Uiso 1 1 d
H29 H 0.0372 0.1747 0.1338 0.128 Uiso 1 1 d
H30 H 0.0430 0.2317 0.0848 0.128 Uiso 1 1 d
H31 H -0.0312 0.1389 0.0858 0.128 Uiso 1 1 d
H32 H 0.695(3) 0.2672(19) 0.1932(11) 0.039 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'
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
O1 Si C19 108.26(15)
O1 Si C20 110.35(15)
C19 Si C20 108.4(3)
O1 Si C15 105.12(9)
C19 Si C15 113.0(2)
C20 Si C15 111.68(16)
C1 O1 Si 127.21(12)
O1 C1 C2 109.05(16)
O1 C1 C9 109.66(15)
C2 C1 C9 102.02(15)
C1 C2 C3 103.61(16)
C2 C3 C4 106.49(15)
O2 C4 C5 109.31(15)
O2 C4 C3 112.15(15)
C5 C4 C3 110.77(16)
O2 C4 C9 108.95(15)
C5 C4 C9 110.98(15)
C3 C4 C9 104.60(15)
C6 C5 C4 114.57(16)
C7 C6 C5 109.64(17)
C8 C7 C14 108.15(18)
C8 C7 C6 122.79(18)
C14 C7 C6 127.83(18)
C7 C8 C9 127.17(17)
C7 C8 C12 114.92(17)
C9 C8 C12 112.91(16)
C8 C9 C1 116.01(15)
C8 C9 C4 111.56(15)
C1 C9 C4 103.45(14)
C8 C9 C10 99.87(14)
C1 C9 C10 109.47(15)
C4 C9 C10 117.07(15)
C11 C10 C9 107.58(16)
C12 C11 C10 106.41(18)
C8 C12 C13 103.43(17)
C8 C12 C11 98.21(17)
C13 C12 C11 117.8(2)
C14 C13 C12 105.11(17)
O3 C14 C7 126.5(2)
O3 C14 C13 125.2(2)
C7 C14 C13 108.17(17)
C16 C15 C18 109.3(3)
C16 C15 C17 109.7(2)
C18 C15 C17 108.2(3)
C16 C15 Si 108.9(2)
C18 C15 Si 110.0(2)
C17 C15 Si 110.69(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Si O1 1.6357(14)
Si C19 1.836(4)
Si C20 1.848(4)
Si C15 1.867(2)
O1 C1 1.427(2)
O2 C4 1.433(2)
O3 C14 1.220(3)
C1 C2 1.523(3)
C1 C9 1.541(2)
C2 C3 1.531(3)
C3 C4 1.554(3)
C4 C5 1.540(3)
C4 C9 1.558(2)
C5 C6 1.530(3)
C6 C7 1.498(3)
C7 C8 1.327(3)
C7 C14 1.474(3)
C8 C9 1.488(2)
C8 C12 1.494(3)
C9 C10 1.566(3)
C10 C11 1.539(3)
C11 C12 1.539(3)
C12 C13 1.524(3)
C13 C14 1.521(3)
C15 C16 1.518(4)
C15 C18 1.521(5)
C15 C17 1.536(3)
