#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:04:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180464 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/33/7213315.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7213315
loop_
_publ_author_name
'Delas, Christophe'
'Blacque, Olivier'
'Moïse, Claude'
_publ_section_title
;
 Study of a tandem aldol--Tischtschenko reaction between chiral
 enolsilanes and aldehydes catalyzed by titanium(IV) isopropoxide
;
_journal_issue                   14
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2265
_journal_paper_doi               10.1039/b002008g
_journal_year                    2000
_chemical_formula_moiety         'C12 H26 O3'
_chemical_formula_sum            'C12 H26 O3'
_chemical_formula_weight         218.33
_chemical_name_systematic
; 
 (3SR,4SR,5SR,6RS,7RS)-2,4,6-trimethyl-nonane-3,5,7-triol 
;
_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                71.339(5)
_cell_angle_beta                 78.603(8)
_cell_angle_gamma                81.054(5)
_cell_formula_units_Z            2
_cell_length_a                   7.347(1)
_cell_length_b                   7.874(1)
_cell_length_c                   12.715(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      2.1
_cell_volume                     679.77(14)
_computing_cell_refinement       'CAD4 EXPRESS'
_computing_data_collection       'CAD4 EXPRESS'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_molecular_graphics    ORTEP3
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       Omega-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  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2962
_diffrn_reflns_theta_full        26.30
_diffrn_reflns_theta_max         26.30
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.067
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0765P)²+0.0718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1371
_reflns_number_gt                2046
_reflns_number_total             2754
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b002008gsup1.cif
_cod_data_source_block           compound22
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0765P)^2^+0.0718P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0765P)^2^+0.0718P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        679.7(1)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7213315
loop_
_symmetry_equiv_pos_as_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_calc_flag
_atom_site_refinement_flags
O1 O -0.00957(14) 1.11383(12) 0.59358(8) 0.0496(3) Uani 1 d .
O2 O 0.06040(16) 0.66296(14) 0.61499(8) 0.0561(3) Uani 1 d .
O3 O -0.09763(19) 0.36970(15) 0.70391(10) 0.0751(4) Uani 1 d .
C1 C 0.3492(3) 1.2727(3) 0.53537(18) 0.0904(6) Uani 1 d .
H1A H 0.4372 1.3369 0.5503 0.118 Uiso 1 calc R
H1B H 0.2391 1.3522 0.5176 0.118 Uiso 1 calc R
H1C H 0.4040 1.2283 0.4729 0.118 Uiso 1 calc R
C2 C 0.2977(2) 1.1159(2) 0.63817(14) 0.0672(4) Uani 1 d .
H2A H 0.2456 1.1621 0.7011 0.087 Uiso 1 calc R
H2B H 0.4104 1.0383 0.6565 0.087 Uiso 1 calc R
C3 C 0.15821(19) 1.00384(18) 0.62378(11) 0.0484(3) Uani 1 d .
H3 H 0.2151 0.9563 0.5611 0.063 Uiso 1 calc R
C4 C 0.11036(17) 0.84230(17) 0.72691(10) 0.0459(3) Uani 1 d .
H4 H 0.0495 0.8891 0.7893 0.060 Uiso 1 calc R
C5 C -0.02877(17) 0.73569(16) 0.70463(10) 0.0412(3) Uani 1 d .
H5 H -0.1357 0.8198 0.6794 0.054 Uiso 1 calc R
C6 C -0.10245(18) 0.58167(16) 0.80721(10) 0.0435(3) Uani 1 d .
H6 H 0.0051 0.5057 0.8379 0.057 Uiso 1 calc R
C7 C -0.21610(19) 0.46333(17) 0.77462(11) 0.0483(3) Uani 1 d .
H7 H -0.3097 0.5429 0.7315 0.063 Uiso 1 calc R
C8 C -0.3174(2) 0.3225(2) 0.87160(13) 0.0610(4) Uani 1 d .
H8 H -0.4027 0.3856 0.9197 0.079 Uiso 1 calc R
C9 C -0.4341(3) 0.2244(3) 0.82747(19) 0.0891(6) Uani 1 d .
H9A H -0.4970 0.1363 0.8894 0.116 Uiso 1 calc R
H9B H -0.3542 0.1656 0.7773 0.116 Uiso 1 calc R
H9C H -0.5245 0.3095 0.7879 0.116 Uiso 1 calc R
C10 C -0.1845(3) 0.1883(2) 0.94348(16) 0.0843(6) Uani 1 d .
H10A H -0.2544 0.1031 1.0035 0.110 Uiso 1 calc R
H10B H -0.1173 0.2514 0.9743 0.110 Uiso 1 calc R
H10C H -0.0979 0.1258 0.8979 0.110 Uiso 1 calc R
C11 C -0.2175(2) 0.6611(2) 0.89768(13) 0.0644(4) Uani 1 d .
H11A H -0.1427 0.7336 0.9165 0.084 Uiso 1 calc R
H11B H -0.2567 0.5652 0.9635 0.084 Uiso 1 calc R
H11C H -0.3251 0.7343 0.8698 0.084 Uiso 1 calc R
C12 C 0.2848(2) 0.7211(2) 0.76228(14) 0.0712(5) Uani 1 d .
H12A H 0.2496 0.6222 0.8272 0.093 Uiso 1 calc R
H12B H 0.3657 0.7892 0.7800 0.093 Uiso 1 calc R
H12C H 0.3488 0.6755 0.7018 0.093 Uiso 1 calc R
HO1 H -0.045(2) 1.174(2) 0.6356(15) 0.067(5) Uiso 1 d .
HO2 H 0.047(3) 0.738(3) 0.5521(18) 0.085(6) Uiso 1 d .
HO3 H -0.028(3) 0.444(3) 0.6593(18) 0.090(7) Uiso 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0659(6) 0.0408(5) 0.0452(5) -0.0163(4) -0.0088(4) -0.0066(4)
O2 0.0830(7) 0.0443(5) 0.0394(5) -0.0151(4) 0.0005(5) -0.0093(5)
O3 0.1071(10) 0.0483(6) 0.0708(7) -0.0310(6) 0.0191(7) -0.0248(6)
C1 0.0925(14) 0.0837(13) 0.0921(13) -0.0169(11) 0.0084(11) -0.0495(11)
C2 0.0662(10) 0.0663(10) 0.0732(10) -0.0185(8) -0.0077(8) -0.0280(8)
C3 0.0523(7) 0.0479(7) 0.0464(7) -0.0169(6) -0.0015(6) -0.0112(6)
C4 0.0469(7) 0.0496(7) 0.0425(6) -0.0146(6) -0.0058(5) -0.0086(6)
C5 0.0465(7) 0.0372(6) 0.0403(6) -0.0134(5) -0.0056(5) -0.0027(5)
C6 0.0484(7) 0.0403(7) 0.0412(6) -0.0114(5) -0.0062(5) -0.0052(5)
C7 0.0573(8) 0.0387(7) 0.0500(7) -0.0145(6) -0.0083(6) -0.0059(6)
C8 0.0682(9) 0.0511(8) 0.0630(9) -0.0162(7) 0.0010(7) -0.0201(7)
C9 0.0940(14) 0.0716(12) 0.1075(15) -0.0218(11) -0.0135(11) -0.0396(11)
C10 0.1137(15) 0.0591(10) 0.0699(11) 0.0052(8) -0.0193(10) -0.0248(10)
C11 0.0780(10) 0.0661(10) 0.0535(8) -0.0281(7) 0.0115(7) -0.0263(8)
C12 0.0538(9) 0.0784(11) 0.0703(10) -0.0001(8) -0.0183(7) -0.0107(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 C2 C3 114.00(14)
O1 C3 C2 110.91(12)
O1 C3 C4 109.89(10)
C2 C3 C4 113.87(11)
C12 C4 C3 111.81(11)
C12 C4 C5 111.21(12)
C3 C4 C5 110.40(10)
O2 C5 C4 108.24(10)
O2 C5 C6 109.20(10)
C4 C5 C6 114.73(10)
C11 C6 C7 111.43(11)
C11 C6 C5 109.31(11)
C7 C6 C5 111.75(10)
O3 C7 C8 106.92(11)
O3 C7 C6 109.92(11)
C8 C7 C6 116.14(11)
C9 C8 C10 110.42(15)
C9 C8 C7 110.36(13)
C10 C8 C7 112.49(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.4349(17)
O2 C5 1.4360(15)
O3 C7 1.4229(17)
C1 C2 1.514(2)
C2 C3 1.5237(19)
C3 C4 1.5332(18)
C4 C12 1.526(2)
C4 C5 1.5373(17)
C5 C6 1.5420(17)
C6 C11 1.5298(18)
C6 C7 1.5372(18)
C7 C8 1.5241(19)
C8 C9 1.523(2)
C8 C10 1.523(2)
