#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178424 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/45/4024542.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_4024542
loop_
_publ_author_name
'Kerstin Rohr'
'Robert Herre'
'Rainer Mahrwald'
_publ_section_title
;
Toward Asymmetric Aldol-Tishchenko Reactions with Enolizable Aldehydes:
Access to Defined Configured Stereotriads, Tetrads, and Stereopentads
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3744
_journal_page_last               3749
_journal_paper_doi               10.1021/jo9003635
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C23 H34 O3'
_chemical_formula_sum            'C23 H34 O3'
_chemical_formula_weight         358.50
_chemical_name_systematic
; 
 1-cyclohexyl-3-hydroxy-2-mthyl-3-phenylpropyl cyclohexanecarboxylate 
;
_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                93.836(10)
_cell_angle_beta                 111.469(9)
_cell_angle_gamma                95.665(9)
_cell_formula_units_Z            2
_cell_length_a                   9.4139(11)
_cell_length_b                   10.6583(12)
_cell_length_c                   10.9899(14)
_cell_measurement_reflns_used    2000
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      5
_cell_volume                     1014.8(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_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  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0804
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            11322
_diffrn_reflns_theta_full        29.26
_diffrn_reflns_theta_max         29.26
_diffrn_reflns_theta_min         3.61
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_correction_T_min  0.9880
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         5260
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0602
_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)+(0.0553P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1230
_reflns_number_gt                3120
_reflns_number_total             5260
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo9003635_si_003.cif
_cod_data_source_block           herr10
_cod_database_code               4024542
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5646(3) 0.16937(19) 0.38311(17) 0.0283(5) Uani 1 1 d D . .
C2 C 0.5137(2) 0.20177(18) 0.49463(16) 0.0210(4) Uani 1 1 d . A .
H2 H 0.5175 0.1251 0.5429 0.025 Uiso 1 1 calc R . .
C3 C 0.3470(2) 0.2308(2) 0.44528(19) 0.0309(5) Uani 1 1 d . . .
H3A H 0.3395 0.3094 0.4014 0.037 Uiso 1 1 calc R A .
H3B H 0.2790 0.1605 0.3803 0.037 Uiso 1 1 calc R . .
C4 C 0.2953(2) 0.2472(2) 0.5607(2) 0.0365(5) Uani 1 1 d . A .
H4A H 0.1887 0.2686 0.5287 0.044 Uiso 1 1 calc R . .
H4B H 0.2953 0.1662 0.5999 0.044 Uiso 1 1 calc R . .
C5 C 0.3996(3) 0.3506(2) 0.6650(2) 0.0350(5) Uani 1 1 d . . .
H5A H 0.3682 0.3534 0.7418 0.042 Uiso 1 1 calc R A .
H5B H 0.3884 0.4336 0.6296 0.042 Uiso 1 1 calc R . .
C6 C 0.5669(2) 0.3281(2) 0.70898(18) 0.0313(5) Uani 1 1 d . A .
H6A H 0.5807 0.2515 0.7562 0.038 Uiso 1 1 calc R . .
H6B H 0.6326 0.4012 0.7710 0.038 Uiso 1 1 calc R . .
C7 C 0.6184(2) 0.31042(19) 0.59312(17) 0.0246(4) Uani 1 1 d . . .
H7A H 0.6139 0.3895 0.5502 0.029 Uiso 1 1 calc R A .
H7B H 0.7261 0.2917 0.6249 0.029 Uiso 1 1 calc R . .
C8 C 0.59403(19) 0.23765(16) 0.18856(15) 0.0165(3) Uani 1 1 d . . .
H8 H 0.6323 0.1533 0.1903 0.020 Uiso 1 1 calc R A .
C9 C 0.44559(19) 0.23096(16) 0.06719(15) 0.0169(3) Uani 1 1 d . A .
H9 H 0.4734 0.2180 -0.0118 0.020 Uiso 1 1 calc R . .
C10 C 0.3722(2) 0.35348(17) 0.05790(18) 0.0244(4) Uani 1 1 d . . .
H10A H 0.3394 0.3675 0.1321 0.037 Uiso 1 1 calc R A .
H10B H 0.2827 0.3465 -0.0248 0.037 Uiso 1 1 calc R . .
H10C H 0.4476 0.4250 0.0605 0.037 Uiso 1 1 calc R . .
C11 C 0.32855(19) 0.11677(16) 0.06046(16) 0.0167(3) Uani 1 1 d . . .
H11 H 0.2967 0.1296 0.1373 0.020 Uiso 1 1 calc R A .
C12 C 0.18576(19) 0.10365(16) -0.06435(16) 0.0171(3) Uani 1 1 d . A .
C13 C 0.1923(2) 0.06586(18) -0.18565(17) 0.0225(4) Uani 1 1 d . . .
H13 H 0.2875 0.0490 -0.1903 0.027 Uiso 1 1 calc R A .
C14 C 0.0621(2) 0.0527(2) -0.29903(18) 0.0300(5) Uani 1 1 d . A .
H14 H 0.0679 0.0257 -0.3811 0.036 Uiso 1 1 calc R . .
C15 C -0.0771(2) 0.0785(2) -0.29395(19) 0.0329(5) Uani 1 1 d . . .
H15 H -0.1665 0.0704 -0.3723 0.039 Uiso 1 1 calc R A .
C16 C -0.0851(2) 0.1162(2) -0.1739(2) 0.0320(5) Uani 1 1 d . A .
H16 H -0.1803 0.1337 -0.1696 0.038 Uiso 1 1 calc R . .
C17 C 0.0455(2) 0.12833(18) -0.06010(17) 0.0237(4) Uani 1 1 d . . .
H17 H 0.0391 0.1539 0.0220 0.028 Uiso 1 1 calc R A .
C18 C 0.7238(2) 0.33909(17) 0.19771(16) 0.0174(3) Uani 1 1 d . A .
H18 H 0.6850 0.4233 0.1933 0.021 Uiso 1 1 calc R . .
C19 C 0.8619(2) 0.34350(19) 0.32747(17) 0.0257(4) Uani 1 1 d . . .
H19A H 0.8302 0.3654 0.4019 0.031 Uiso 1 1 calc R A .
H19B H 0.8963 0.2586 0.3362 0.031 Uiso 1 1 calc R . .
C20 C 0.9956(2) 0.4406(2) 0.33415(19) 0.0318(5) Uani 1 1 d . A .
H20A H 1.0837 0.4392 0.4179 0.038 Uiso 1 1 calc R . .
H20B H 0.9640 0.5266 0.3324 0.038 Uiso 1 1 calc R . .
C21 C 1.0452(2) 0.4118(2) 0.21866(19) 0.0282(4) Uani 1 1 d . . .
H21A H 1.1288 0.4780 0.2226 0.034 Uiso 1 1 calc R A .
H21B H 1.0855 0.3291 0.2248 0.034 Uiso 1 1 calc R . .
C22 C 0.9104(2) 0.40759(19) 0.08898(17) 0.0233(4) Uani 1 1 d . A .
H22A H 0.8786 0.4933 0.0784 0.028 Uiso 1 1 calc R . .
H22B H 0.9431 0.3829 0.0158 0.028 Uiso 1 1 calc R . .
C23 C 0.7744(2) 0.31436(18) 0.08178(16) 0.0210(4) Uani 1 1 d . . .
H23A H 0.8022 0.2273 0.0798 0.025 Uiso 1 1 calc R A .
H23B H 0.6868 0.3195 -0.0012 0.025 Uiso 1 1 calc R . .
O1S O 0.6568(4) 0.0885(3) 0.3880(3) 0.0271(6) Uani 0.50 1 d PDU A 2
O1 O 0.5598(4) 0.0569(3) 0.3436(3) 0.0252(6) Uani 0.50 1 d PDU A 1
O2 O 0.55376(14) 0.26028(11) 0.30443(11) 0.0190(3) Uani 1 1 d . A .
O3 O 0.39661(14) 0.00153(11) 0.06868(11) 0.0198(3) Uani 1 1 d . A .
H3 H 0.4490 -0.0054 0.1477 0.030 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 121.56(19) . . ?
O1S C1 O2 119.8(2) . . ?
O1 C1 C2 119.9(2) . . ?
O1S C1 C2 122.55(19) . . ?
O2 C1 C2 113.38(15) . . ?
C1 C2 C7 113.32(17) . . ?
C1 C2 C3 111.90(15) . . ?
C7 C2 C3 109.78(15) . . ?
C1 C2 H2 107.2 . . ?
C7 C2 H2 107.2 . . ?
C3 C2 H2 107.2 . . ?
C4 C3 C2 109.63(16) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 111.61(18) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 111.36(16) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 112.00(16) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C2 C7 C6 109.55(17) . . ?
C2 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
C2 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
O2 C8 C18 108.63(13) . . ?
O2 C8 C9 107.14(13) . . ?
C18 C8 C9 115.93(14) . . ?
O2 C8 H8 108.3 . . ?
C18 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
C10 C9 C8 112.90(14) . . ?
C10 C9 C11 110.51(14) . . ?
C8 C9 C11 111.57(14) . . ?
C10 C9 H9 107.2 . . ?
C8 C9 H9 107.2 . . ?
C11 C9 H9 107.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 C12 109.18(13) . . ?
O3 C11 C9 110.75(13) . . ?
C12 C11 C9 112.04(14) . . ?
O3 C11 H11 108.3 . . ?
C12 C11 H11 108.3 . . ?
C9 C11 H11 108.3 . . ?
C17 C12 C13 118.59(16) . . ?
C17 C12 C11 120.76(15) . . ?
C13 C12 C11 120.65(15) . . ?
C14 C13 C12 120.67(17) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.32(18) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.53(18) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.03(18) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 120.85(17) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C8 C18 C23 110.02(13) . . ?
C8 C18 C19 111.41(14) . . ?
C23 C18 C19 109.70(15) . . ?
C8 C18 H18 108.5 . . ?
C23 C18 H18 108.5 . . ?
C19 C18 H18 108.5 . . ?
C20 C19 C18 111.61(16) . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 C21 110.83(16) . . ?
C19 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C22 C21 C20 110.57(16) . . ?
C22 C21 H21A 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C23 C22 C21 111.76(16) . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 C18 112.91(15) . . ?
C22 C23 H23A 109.0 . . ?
C18 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C18 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C1 O2 C8 118.52(13) . . ?
C11 O3 H3 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.238(3) . ?
C1 O1S 1.272(3) . ?
C1 O2 1.328(2) . ?
C1 C2 1.502(2) . ?
C2 C7 1.520(3) . ?
C2 C3 1.533(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.522(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.511(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.518(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.526(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O2 1.4675(19) . ?
C8 C18 1.518(2) . ?
C8 C9 1.530(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.529(2) . ?
C9 C11 1.538(2) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O3 1.434(2) . ?
C11 C12 1.515(2) . ?
C11 H11 1.0000 . ?
C12 C17 1.388(2) . ?
C12 C13 1.392(2) . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.531(2) . ?
C18 C19 1.532(2) . ?
C18 H18 1.0000 . ?
C19 C20 1.525(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.528(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.517(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.515(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
O3 H3 0.8400 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 138.1(3) . . . . ?
O1S C1 C2 C7 89.8(3) . . . . ?
O2 C1 C2 C7 -66.8(2) . . . . ?
O1 C1 C2 C3 -97.1(3) . . . . ?
O1S C1 C2 C3 -145.4(3) . . . . ?
O2 C1 C2 C3 57.9(2) . . . . ?
C1 C2 C3 C4 173.21(18) . . . . ?
C7 C2 C3 C4 -60.1(2) . . . . ?
C2 C3 C4 C5 57.2(2) . . . . ?
C3 C4 C5 C6 -54.1(2) . . . . ?
C4 C5 C6 C7 53.8(2) . . . . ?
C1 C2 C7 C6 -174.59(16) . . . . ?
C3 C2 C7 C6 59.5(2) . . . . ?
C5 C6 C7 C2 -56.6(2) . . . . ?
O2 C8 C9 C10 60.66(18) . . . . ?
C18 C8 C9 C10 -60.78(19) . . . . ?
O2 C8 C9 C11 -64.50(16) . . . . ?
C18 C8 C9 C11 174.05(13) . . . . ?
C10 C9 C11 O3 179.81(13) . . . . ?
C8 C9 C11 O3 -53.70(17) . . . . ?
C10 C9 C11 C12 57.65(17) . . . . ?
C8 C9 C11 C12 -175.86(14) . . . . ?
O3 C11 C12 C17 127.01(18) . . . . ?
C9 C11 C12 C17 -109.94(18) . . . . ?
O3 C11 C12 C13 -52.6(2) . . . . ?
C9 C11 C12 C13 70.4(2) . . . . ?
C17 C12 C13 C14 -0.3(3) . . . . ?
C11 C12 C13 C14 179.33(18) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C12 0.3(3) . . . . ?
C13 C12 C17 C16 -0.2(3) . . . . ?
C11 C12 C17 C16 -179.87(18) . . . . ?
O2 C8 C18 C23 177.10(14) . . . . ?
C9 C8 C18 C23 -62.25(18) . . . . ?
O2 C8 C18 C19 55.21(18) . . . . ?
C9 C8 C18 C19 175.86(14) . . . . ?
C8 C18 C19 C20 177.12(15) . . . . ?
C23 C18 C19 C20 55.0(2) . . . . ?
C18 C19 C20 C21 -57.5(2) . . . . ?
C19 C20 C21 C22 56.7(2) . . . . ?
C20 C21 C22 C23 -55.0(2) . . . . ?
C21 C22 C23 C18 54.5(2) . . . . ?
C8 C18 C23 C22 -176.51(15) . . . . ?
C19 C18 C23 C22 -53.6(2) . . . . ?
O1 C1 O2 C8 -22.9(3) . . . . ?
O1S C1 O2 C8 25.2(3) . . . . ?
C2 C1 O2 C8 -177.47(15) . . . . ?
C18 C8 O2 C1 -121.14(17) . . . . ?
C9 C8 O2 C1 112.93(17) . . . . ?
