#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/36/7103630.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_7103630
loop_
_publ_author_name
'Schmittel, Michael'
'Haeuseler, Andreas'
'Nilges, Tom'
'Pfitzner, Arno'
_publ_section_title
;
 The elusive aldol reaction of enolates with aldolates -- a highly
 stereoselective process using three different carbonyl components
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   1
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              34
_journal_page_last               35
_journal_paper_doi               10.1039/b209536j
_journal_year                    2003
_chemical_formula_sum            'C21 H26 O3'
_chemical_formula_weight         326.42
_chemical_name_systematic
;
 2-Ethyl-3,5-dimethyl-4,6-diphenyl-tetrahydropyran-2,4-diol
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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            4
_cell_length_a                   10.9177(9)
_cell_length_b                   17.2334(10)
_cell_length_c                   9.4999(5)
_cell_measurement_reflns_used    7998
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.4
_cell_volume                     1787.4(2)
_computing_cell_refinement       'STOE CELL'
_computing_data_collection       'STOE EXPOSE'
_computing_data_reduction        'STOE INTEGRATE'
_computing_molecular_graphics    DIAMOND
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'STOE IPDS I'
_diffrn_measurement_method       'image plate data from phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27347
_diffrn_reflns_theta_full        28.11
_diffrn_reflns_theta_max         28.11
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       isometric
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(6)
_refine_ls_extinction_coef       0.0117(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4247
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0292
_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)+(0.0515P)²+0.0609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0746
_reflns_d_resolution_high        0.7543
_reflns_number_gt                3926
_reflns_number_total             4247
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b209536j.txt
_cod_data_source_block           oci2
_cod_database_code               7103630
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.22822(6) 0.09180(5) 0.85361(8) 0.02143(17) Uani 1 1 d . . .
O2 O -0.03994(7) 0.03039(4) 0.88803(10) 0.02342(17) Uani 1 1 d . . .
OH2 H 0.0087(15) 0.0302(10) 0.538(2) 0.041(5) Uiso 1 1 d . . .
O3 O 0.00708(7) 0.05319(4) 0.62375(9) 0.02003(15) Uani 1 1 d . . .
OH3 H -0.0178(17) 0.0202(10) 0.805(2) 0.044(5) Uiso 1 1 d . . .
C1 C -0.10198(9) 0.10306(6) 0.88514(12) 0.0188(2) Uani 1 1 d . . .
C2 C -0.04417(9) 0.15764(6) 0.77485(11) 0.0179(2) Uani 1 1 d . . .
H2 H -0.0930(11) 0.2083(7) 0.7803(15) 0.016(3) Uiso 1 1 d . . .
C3 C -0.06179(8) 0.12418(6) 0.62510(12) 0.01724(19) Uani 1 1 d . . .
C4 C -0.19971(9) 0.10763(6) 0.59882(11) 0.0184(2) Uani 1 1 d . . .
H4 H -0.2440(11) 0.1582(7) 0.5985(15) 0.016(3) Uiso 1 1 d . . .
C5 C -0.25297(9) 0.05767(6) 0.71849(13) 0.0196(2) Uani 1 1 d . . .
H5 H -0.2140(13) 0.0056(9) 0.7143(17) 0.026(4) Uiso 1 1 d . . .
C6 C -0.09904(10) 0.13374(7) 1.03547(13) 0.0246(2) Uani 1 1 d . . .
H61 H -0.1396(15) 0.0940(9) 1.0942(18) 0.036(4) Uiso 1 1 d . . .
H62 H -0.0109(14) 0.1334(8) 1.0700(19) 0.032(4) Uiso 1 1 d . . .
C7 C -0.15550(14) 0.21317(9) 1.05686(17) 0.0371(3) Uani 1 1 d . . .
H71 H -0.1553(16) 0.2278(10) 1.156(2) 0.046(5) Uiso 1 1 d . . .
H72 H -0.1127(19) 0.2564(13) 1.002(2) 0.060(5) Uiso 1 1 d . . .
H73 H -0.2395(17) 0.2130(10) 1.026(2) 0.047(5) Uiso 1 1 d . . .
C8 C 0.08985(10) 0.17516(7) 0.80896(14) 0.0256(2) Uani 1 1 d . . .
H81 H 0.1270(17) 0.2085(10) 0.735(2) 0.048(5) Uiso 1 1 d . . .
H82 H 0.0987(14) 0.2059(9) 0.900(2) 0.038(4) Uiso 1 1 d . . .
H83 H 0.1383(15) 0.1253(9) 0.812(2) 0.036(4) Uiso 1 1 d . . .
C9 C -0.22113(10) 0.06969(7) 0.45567(13) 0.0248(2) Uani 1 1 d . . .
H91 H -0.1811(16) 0.0992(10) 0.377(2) 0.046(5) Uiso 1 1 d . . .
H92 H -0.1870(14) 0.0134(9) 0.450(2) 0.037(4) Uiso 1 1 d . . .
H93 H -0.3104(15) 0.0676(8) 0.4341(18) 0.032(4) Uiso 1 1 d . . .
C10 C -0.01260(9) 0.18078(6) 0.51421(12) 0.0212(2) Uani 1 1 d . . .
C11 C 0.08623(11) 0.16163(7) 0.42919(14) 0.0291(3) Uani 1 1 d . . .
H111 H 0.1302(16) 0.1118(9) 0.4396(19) 0.037(4) Uiso 1 1 d . . .
C12 C 0.12906(12) 0.21392(8) 0.32876(15) 0.0365(3) Uani 1 1 d . . .
H121 H 0.1997(18) 0.1962(10) 0.265(2) 0.055(5) Uiso 1 1 d . . .
C13 C 0.07558(14) 0.28616(8) 0.31375(16) 0.0391(3) Uani 1 1 d . . .
H131 H 0.1078(15) 0.3246(9) 0.243(2) 0.042(4) Uiso 1 1 d . . .
C14 C -0.02157(13) 0.30628(8) 0.39933(16) 0.0355(3) Uani 1 1 d . . .
H141 H -0.0607(16) 0.3572(10) 0.394(2) 0.043(4) Uiso 1 1 d . . .
C15 C -0.06626(11) 0.25396(7) 0.49861(14) 0.0277(2) Uani 1 1 d . . .
H151 H -0.1359(15) 0.2685(9) 0.560(2) 0.037(4) Uiso 1 1 d . . .
C16 C -0.39101(9) 0.05011(6) 0.70758(12) 0.0218(2) Uani 1 1 d . . .
C17 C -0.46722(10) 0.10531(7) 0.76893(14) 0.0259(2) Uani 1 1 d . . .
H171 H -0.4334(16) 0.1486(9) 0.824(2) 0.040(4) Uiso 1 1 d . . .
C18 C -0.59382(10) 0.10035(8) 0.75372(15) 0.0311(3) Uani 1 1 d . . .
H181 H -0.6466(17) 0.1408(10) 0.799(2) 0.048(5) Uiso 1 1 d . . .
C19 C -0.64518(10) 0.04095(8) 0.67495(15) 0.0326(3) Uani 1 1 d . . .
H191 H -0.7364(14) 0.0381(9) 0.6609(18) 0.032(4) Uiso 1 1 d . . .
C20 C -0.57066(11) -0.01425(8) 0.61435(16) 0.0339(3) Uani 1 1 d . . .
H201 H -0.6019(16) -0.0554(9) 0.557(2) 0.043(5) Uiso 1 1 d . . .
C22 C -0.44385(11) -0.01062(7) 0.63231(15) 0.0292(2) Uani 1 1 d . . .
H221 H -0.3894(16) -0.0509(9) 0.589(2) 0.042(5) 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'
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
C1 O1 C5 115.18(8) . . ?
O1 C1 O2 110.16(8) . . ?
O1 C1 C6 105.36(8) . . ?
O2 C1 C6 106.09(9) . . ?
O1 C1 C2 109.65(8) . . ?
O2 C1 C2 110.77(8) . . ?
C6 C1 C2 114.62(9) . . ?
C8 C2 C1 111.59(9) . . ?
C8 C2 C3 112.81(9) . . ?
C1 C2 C3 110.26(8) . . ?
O3 C3 C10 110.64(8) . . ?
O3 C3 C2 105.11(8) . . ?
C10 C3 C2 110.56(8) . . ?
O3 C3 C4 110.48(8) . . ?
C10 C3 C4 110.25(9) . . ?
C2 C3 C4 109.69(8) . . ?
C9 C4 C5 111.12(8) . . ?
C9 C4 C3 111.74(9) . . ?
C5 C4 C3 110.49(8) . . ?
O1 C5 C16 106.45(9) . . ?
O1 C5 C4 111.07(8) . . ?
C16 C5 C4 111.89(9) . . ?
C7 C6 C1 115.52(10) . . ?
C11 C10 C15 118.59(11) . . ?
C11 C10 C3 121.40(10) . . ?
C15 C10 C3 119.99(10) . . ?
C10 C11 C12 120.38(12) . . ?
C13 C12 C11 120.76(12) . . ?
C14 C13 C12 119.33(12) . . ?
C13 C14 C15 120.35(12) . . ?
C14 C15 C10 120.57(12) . . ?
C17 C16 C22 118.75(10) . . ?
C17 C16 C5 120.45(10) . . ?
C22 C16 C5 120.77(10) . . ?
C16 C17 C18 120.53(11) . . ?
C19 C18 C17 120.19(12) . . ?
C20 C19 C18 119.76(11) . . ?
C19 C20 C22 120.23(12) . . ?
C16 C22 C20 120.48(12) . . ?
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
O1 C1 1.4237(11) . ?
O1 C5 1.4376(13) . ?
O2 C1 1.4241(12) . ?
O3 C3 1.4360(11) . ?
C1 C6 1.5232(16) . ?
C1 C2 1.5429(15) . ?
C2 C8 1.5287(14) . ?
C2 C3 1.5470(15) . ?
C3 C10 1.5329(14) . ?
C3 C4 1.5527(13) . ?
C4 C9 1.5269(16) . ?
C4 C5 1.5400(15) . ?
C5 C16 1.5162(14) . ?
C6 C7 1.5150(17) . ?
C10 C11 1.3876(16) . ?
C10 C15 1.3984(16) . ?
C11 C12 1.3932(18) . ?
C12 C13 1.382(2) . ?
C13 C14 1.381(2) . ?
C14 C15 1.3930(18) . ?
C16 C17 1.3918(16) . ?
C16 C22 1.3925(16) . ?
C17 C18 1.3923(15) . ?
C18 C19 1.3865(19) . ?
C19 C20 1.378(2) . ?
C20 C22 1.3964(16) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139180715
