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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/54/7105403.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_7105403
loop_
_publ_author_name
'Sonawane, Manoj R.'
'Císařová, Ivana'
'Lyapkalo, Ilya M.'
_publ_section_title
;
 N-Trimethylsilyloxyenamines as new aldehyde enolate synthons: general,
 efficient and diastereoselective aldol reaction with ketals and acetals
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   15
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2656
_journal_page_last               2658
_journal_paper_doi               10.1039/b924880c
_journal_volume                  46
_journal_year                    2010
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C16 H25 N O2'
_chemical_formula_sum            'C16 H25 N O2'
_chemical_formula_weight         263.37
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.4557(15)
_cell_angle_beta                 95.3665(18)
_cell_angle_gamma                106.3773(17)
_cell_formula_units_Z            2
_cell_length_a                   5.9484(2)
_cell_length_b                   8.4271(3)
_cell_length_c                   15.9289(5)
_cell_measurement_reflns_used    3400
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     759.58(4)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15912
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.29
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0373
_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)+(0.0487P)²+0.1937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                3032
_reflns_number_total             3462
_reflns_threshold_expression     I>\2s(I)
_cod_data_source_file            b924880c.txt
_cod_data_source_block           2s
_cod_database_code               7105403
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 0.82949(17) 0.99728(12) 0.33000(6) 0.0215(2) Uani 1 1 d . . .
N2 N 0.64491(14) 0.90888(10) 0.36077(5) 0.02015(18) Uani 1 1 d . . .
C3 C 0.64723(17) 0.75867(12) 0.40826(6) 0.0230(2) Uani 1 1 d . . .
O4 O 0.43837(12) 0.93224(9) 0.34703(5) 0.02816(18) Uani 1 1 d . . .
C5 C 0.4986(2) 0.61055(13) 0.34812(8) 0.0350(3) Uani 1 1 d . . .
H5A H 0.3397 0.6215 0.3350 0.052 Uiso 1 1 calc R . .
H5B H 0.4887 0.5076 0.3751 0.052 Uiso 1 1 calc R . .
H5C H 0.5720 0.6075 0.2957 0.052 Uiso 1 1 calc R . .
C6 C 0.89519(19) 0.74508(14) 0.42932(7) 0.0310(2) Uani 1 1 d . . .
H6A H 0.9653 0.7339 0.3768 0.047 Uiso 1 1 calc R . .
H6B H 0.8885 0.6474 0.4605 0.047 Uiso 1 1 calc R . .
H6C H 0.9917 0.8452 0.4642 0.047 Uiso 1 1 calc R . .
C7 C 0.5351(2) 0.77461(15) 0.48931(7) 0.0327(3) Uani 1 1 d . . .
H7A H 0.6318 0.8732 0.5252 0.049 Uiso 1 1 calc R . .
H7B H 0.5249 0.6756 0.5197 0.049 Uiso 1 1 calc R . .
H7C H 0.3764 0.7853 0.4751 0.049 Uiso 1 1 calc R . .
C8 C 0.80825(17) 1.12523(12) 0.27127(6) 0.0229(2) Uani 1 1 d . . .
H8 H 0.6380 1.0969 0.2483 0.028 Uiso 1 1 calc R . .
C9 C 0.94747(18) 1.11284(12) 0.19458(6) 0.0236(2) Uani 1 1 d . . .
C10 C 0.87828(18) 0.92903(13) 0.16104(6) 0.0241(2) Uani 1 1 d . . .
C11 C 0.6532(2) 0.85441(15) 0.11840(7) 0.0320(2) Uani 1 1 d . . .
H11 H 0.5520 0.9208 0.1047 0.038 Uiso 1 1 calc R . .
C12 C 0.5758(2) 0.68450(16) 0.09579(8) 0.0382(3) Uani 1 1 d . . .
H12 H 0.4222 0.6357 0.0668 0.046 Uiso 1 1 calc R . .
C13 C 0.7206(2) 0.58533(15) 0.11510(7) 0.0360(3) Uani 1 1 d . . .
H13 H 0.6662 0.4688 0.1004 0.043 Uiso 1 1 calc R . .
C14 C 0.9450(2) 0.65790(14) 0.15603(7) 0.0317(2) Uani 1 1 d . . .
H14 H 1.0463 0.5911 0.1687 0.038 Uiso 1 1 calc R . .
C15 C 1.02377(19) 0.82842(13) 0.17885(6) 0.0263(2) Uani 1 1 d . . .
H15 H 1.1785 0.8767 0.2069 0.032 Uiso 1 1 calc R . .
O16 O 0.85607(14) 1.20752(10) 0.13503(5) 0.03069(19) Uani 1 1 d . . .
C17 C 0.9595(3) 1.22246(18) 0.05805(8) 0.0474(4) Uani 1 1 d . . .
H17A H 1.1267 1.2853 0.0698 0.071 Uiso 1 1 calc R . .
H17B H 0.8784 1.2808 0.0198 0.071 Uiso 1 1 calc R . .
H17C H 0.9450 1.1116 0.0314 0.071 Uiso 1 1 calc R . .
C18 C 0.8725(2) 1.29850(13) 0.31868(8) 0.0343(3) Uani 1 1 d . . .
H18A H 0.7607 1.3002 0.3599 0.051 Uiso 1 1 calc R . .
H18B H 0.8654 1.3805 0.2782 0.051 Uiso 1 1 calc R . .
H18C H 1.0325 1.3256 0.3482 0.051 Uiso 1 1 calc R . .
C19 C 1.21243(19) 1.18852(13) 0.21727(7) 0.0300(2) Uani 1 1 d . . .
H19A H 1.2947 1.1627 0.1701 0.045 Uiso 1 1 calc R . .
H19B H 1.2646 1.1423 0.2680 0.045 Uiso 1 1 calc R . .
H19C H 1.2485 1.3093 0.2283 0.045 Uiso 1 1 calc R . .
H1 H 0.976(2) 0.9725(15) 0.3448(8) 0.027(3) 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'
N N 0.0061 0.0033 '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
N2 C1 C8 120.37(9) . . ?
N2 C1 H1 116.9(7) . . ?
C8 C1 H1 122.6(7) . . ?
C1 N2 O4 122.92(8) . . ?
C1 N2 C3 122.53(8) . . ?
O4 N2 C3 114.27(7) . . ?
N2 C3 C6 112.25(8) . . ?
N2 C3 C7 107.56(8) . . ?
C6 C3 C7 110.08(9) . . ?
N2 C3 C5 104.51(8) . . ?
C6 C3 C5 110.52(9) . . ?
C7 C3 C5 111.80(9) . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C8 C18 111.30(8) . . ?
C1 C8 C9 110.22(8) . . ?
C18 C8 C9 114.62(8) . . ?
C1 C8 H8 106.7 . . ?
C18 C8 H8 106.7 . . ?
C9 C8 H8 106.7 . . ?
O16 C9 C19 110.57(8) . . ?
O16 C9 C10 110.59(8) . . ?
C19 C9 C10 113.19(8) . . ?
O16 C9 C8 102.59(7) . . ?
C19 C9 C8 112.26(9) . . ?
C10 C9 C8 107.09(8) . . ?
C15 C10 C11 118.11(10) . . ?
C15 C10 C9 122.14(9) . . ?
C11 C10 C9 119.43(9) . . ?
C12 C11 C10 120.79(10) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.57(11) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.24(11) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 120.44(10) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.84(10) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C17 O16 C9 115.16(8) . . ?
O16 C17 H17A 109.5 . . ?
O16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 C18 H18A 109.5 . . ?
C8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 N2 1.2977(13) . ?
C1 C8 1.4934(13) . ?
C1 H1 0.963(13) . ?
N2 O4 1.2990(10) . ?
N2 C3 1.5160(12) . ?
C3 C6 1.5194(14) . ?
C3 C7 1.5234(14) . ?
C3 C5 1.5272(15) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C18 1.5320(14) . ?
C8 C9 1.5529(13) . ?
C8 H8 1.0000 . ?
C9 O16 1.4393(11) . ?
C9 C19 1.5232(15) . ?
C9 C10 1.5343(14) . ?
C10 C15 1.3947(14) . ?
C10 C11 1.3973(15) . ?
C11 C12 1.3882(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3867(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3819(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3936(15) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
O16 C17 1.4192(13) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139181445
