#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:32:06 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178874 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/03/4110327.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_4110327
loop_
_publ_author_name
'Matthew B. Boxer'
'Hisashi Yamamoto'
_publ_section_title
;
 Tris(trimethylsilyl)silyl-Governed Aldehyde Cross-Aldol Cascade Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              48
_journal_page_last               49
_journal_paper_doi               10.1021/ja054725k
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C8 H18 O2'
_chemical_formula_weight         146.22
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.643(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.631(2)
_cell_length_b                   9.4534(18)
_cell_length_c                   8.2775(16)
_cell_measurement_temperature    100(2)
_cell_volume                     867.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9908
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_correction_T_min  0.9659
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         2100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0424
_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)+(0.0789P)²+0.1333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                1913
_reflns_number_total             2100
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja054725ksi20050714_091209.cif
_cod_data_source_block           box11ss
_cod_database_code               4110327
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
_atom_site_refinement_flags
C1 C 0.04242(9) 0.10154(10) 0.32583(11) 0.0181(2) Uani 1 1 d .
H1A H -0.0040 0.0121 0.3029 0.022 Uiso 1 1 calc R
H1B H 0.0399 0.1383 0.4367 0.022 Uiso 1 1 calc R
C2 C 0.17307(8) 0.07254(9) 0.33337(11) 0.0162(2) Uani 1 1 d .
H2 H 0.2169 0.1649 0.3546 0.019 Uiso 1 1 calc R
C3 C 0.23069(9) -0.02323(11) 0.48596(12) 0.0216(2) Uani 1 1 d .
H3A H 0.2042 0.0067 0.5823 0.032 Uiso 1 1 calc R
H3B H 0.3187 -0.0162 0.5164 0.032 Uiso 1 1 calc R
H3C H 0.2060 -0.1214 0.4567 0.032 Uiso 1 1 calc R
C4 C 0.17934(8) 0.01653(9) 0.16240(11) 0.0142(2) Uani 1 1 d .
H4 H 0.1296 0.0819 0.0735 0.017 Uiso 1 1 calc R
C5 C 0.30538(8) 0.00783(9) 0.13509(12) 0.0168(2) Uani 1 1 d .
C6 C 0.28525(9) -0.01004(10) -0.05563(13) 0.0212(2) Uani 1 1 d .
H6A H 0.3633 -0.0107 -0.0779 0.032 Uiso 1 1 calc R
H6B H 0.2363 0.0687 -0.1170 0.032 Uiso 1 1 calc R
H6C H 0.2433 -0.0995 -0.0939 0.032 Uiso 1 1 calc R
C7 C 0.38190(9) -0.11678(11) 0.22663(14) 0.0251(2) Uani 1 1 d .
H7A H 0.4537 -0.1259 0.1889 0.038 Uiso 1 1 calc R
H7B H 0.3344 -0.2040 0.2004 0.038 Uiso 1 1 calc R
H7C H 0.4066 -0.1002 0.3492 0.038 Uiso 1 1 calc R
C8 C 0.37420(9) 0.14651(11) 0.19153(14) 0.0240(2) Uani 1 1 d .
H8A H 0.3971 0.1542 0.3153 0.036 Uiso 1 1 calc R
H8B H 0.3225 0.2266 0.1401 0.036 Uiso 1 1 calc R
H8C H 0.4470 0.1474 0.1553 0.036 Uiso 1 1 calc R
O1 O -0.01188(6) 0.20251(7) 0.19551(8) 0.01885(19) Uani 1 1 d .
H1 H -0.0493 0.2635 0.2338 0.028 Uiso 1 1 calc R
O2 O 0.11972(6) -0.11867(7) 0.13425(8) 0.01762(19) Uani 1 1 d .
H2A H 0.0916 -0.1335 0.0296 0.026 Uiso 1 1 calc R
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
C1 0.0225(5) 0.0173(4) 0.0162(5) 0.0014(3) 0.0085(4) 0.0027(3)
C2 0.0194(4) 0.0153(4) 0.0134(4) -0.0009(3) 0.0041(3) -0.0002(3)
C3 0.0257(5) 0.0237(5) 0.0133(4) 0.0010(3) 0.0028(4) 0.0013(4)
C4 0.0157(4) 0.0125(4) 0.0146(4) -0.0002(3) 0.0046(3) -0.0010(3)
C5 0.0161(4) 0.0158(4) 0.0188(5) -0.0001(3) 0.0057(3) -0.0006(3)
C6 0.0223(5) 0.0231(5) 0.0214(5) -0.0011(4) 0.0115(4) -0.0010(4)
C7 0.0213(5) 0.0247(5) 0.0294(5) 0.0039(4) 0.0080(4) 0.0072(4)
C8 0.0216(5) 0.0230(5) 0.0282(5) -0.0034(4) 0.0088(4) -0.0064(4)
O1 0.0235(4) 0.0177(4) 0.0159(3) -0.0003(2) 0.0070(3) 0.0052(3)
O2 0.0221(4) 0.0172(4) 0.0142(3) -0.0027(2) 0.0064(3) -0.0066(2)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C2 110.85(7)
C1 C2 C3 108.72(8)
C1 C2 C4 110.45(7)
C3 C2 C4 115.16(8)
O2 C4 C2 107.51(7)
O2 C4 C5 111.07(7)
C2 C4 C5 117.65(7)
C7 C5 C6 108.01(8)
C7 C5 C8 109.60(8)
C6 C5 C8 108.10(8)
C7 C5 C4 113.68(8)
C6 C5 C4 107.43(7)
C8 C5 C4 109.84(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.4355(11)
C1 C2 1.5267(13)
C2 C3 1.5333(13)
C2 C4 1.5333(12)
C4 O2 1.4390(10)
C4 C5 1.5518(13)
C5 C7 1.5315(13)
C5 C6 1.5335(13)
C5 C8 1.5333(13)
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
O1 C1 C2 C3 174.06(7)
O1 C1 C2 C4 -58.68(10)
C1 C2 C4 O2 -65.04(9)
C3 C2 C4 O2 58.57(10)
C1 C2 C4 C5 168.74(7)
C3 C2 C4 C5 -67.64(10)
O2 C4 C5 C7 -48.32(10)
C2 C4 C5 C7 76.14(10)
O2 C4 C5 C6 71.12(9)
C2 C4 C5 C6 -164.42(8)
O2 C4 C5 C8 -171.53(7)
C2 C4 C5 C8 -47.07(11)
