#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151760.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_7151760
loop_
_publ_author_name
'Blangetti, Marco'
'Deagostino, Annamaria'
'Gervasio, Giuliana'
'Marabello, Domenica'
'Prandi, Cristina'
'Venturello, Paolo'
_publ_section_title
;
 Superbase promoted synthesis of dienamides as useful intermediates for
 the synthesis of α-ketoamides, γ-lactams and cyclic imino ethers.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2535
_journal_page_last               2538
_journal_paper_doi               10.1039/c0ob00867b
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C17 H17 N O2'
_chemical_formula_weight         267.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Thu Mar 04 15:55:25 2010'
;
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 103.267(6)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4.00000
_cell_length_a                   8.8274(5)
_cell_length_b                   13.2339(6)
_cell_length_c                   12.3855(7)
_cell_measurement_reflns_used    2797
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.2023
_cell_measurement_theta_min      3.3732
_cell_volume                     1408.27(13)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.2890
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
1 omega -10.00 34.00 1.0000 120.0000
omega____ theta____ kappa____ phi______ frames
- 17.7068 69.0000 2.0000 44

2 omega -12.00 45.00 1.0000 120.0000
omega____ theta____ kappa____ phi______ frames
- 17.7068 69.0000 95.0000 57

3 omega -41.00 20.00 1.0000 120.0000
omega____ theta____ kappa____ phi______ frames
- 17.7068 -37.0000 90.0000 61

4 omega -53.00 28.00 1.0000 120.0000
omega____ theta____ kappa____ phi______ frames
- 17.7068 -37.0000 -30.0000 81

5 omega -51.00 30.00 1.0000 120.0000
omega____ theta____ kappa____ phi______ frames
- 17.7068 -50.0000 -130.0000 81

6 omega -12.00 56.00 1.0000 120.0000
omega____ theta____ kappa____ phi______ frames
- 17.7068 69.0000 -141.0000 68

7 omega -10.00 34.00 1.0000 120.0000
omega____ theta____ kappa____ phi______ frames
- 17.7068 69.0000 2.0000 44

8 omega -12.00 45.00 1.0000 120.0000
omega____ theta____ kappa____ phi______ frames
- 17.7068 69.0000 95.0000 57

;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0424877000
_diffrn_orient_matrix_UB_12      0.0179367000
_diffrn_orient_matrix_UB_13      0.0382426000
_diffrn_orient_matrix_UB_21      -0.0661917000
_diffrn_orient_matrix_UB_22      -0.0275834000
_diffrn_orient_matrix_UB_23      -0.0282571000
_diffrn_orient_matrix_UB_31      0.0251215000
_diffrn_orient_matrix_UB_32      -0.0423105000
_diffrn_orient_matrix_UB_33      0.0346430000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12381
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.2023
_diffrn_reflns_theta_min         3.3732
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0634
_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)+(0.1044P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.1837
_reflns_number_gt                1233
_reflns_number_total             2012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00867b.txt
_cod_data_source_block           compound5a
_cod_original_cell_volume        1408.28(12)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7151760
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
N1 N 0.9662(3) 0.90634(17) 0.8096(2) 0.0487(7) Uani 1 1 d . A .
C1 C 0.8279(4) 0.9292(3) 0.8056(3) 0.0605(9) Uani 1 1 d . . .
O1A O 0.7519(4) 0.9115(3) 0.8893(3) 0.0583(13) Uiso 0.624(6) 1 d P A 1
C2A C 0.6012(7) 0.9650(4) 0.8640(5) 0.0640(18) Uiso 0.624(6) 1 d P A 1
H2AA H 0.5972 1.0128 0.9237 0.077 Uiso 0.624(6) 1 calc PR A 1
C3A C 0.4760(8) 0.8893(5) 0.8553(7) 0.0749(19) Uiso 0.624(6) 1 d P A 1
H3AA H 0.4857 0.8563 0.9255 0.112 Uiso 0.624(6) 1 calc PR A 1
H3AB H 0.4842 0.8402 0.7999 0.112 Uiso 0.624(6) 1 calc PR A 1
H3AC H 0.3767 0.9224 0.8347 0.112 Uiso 0.624(6) 1 calc PR A 1
C5A C 0.6023(7) 1.0204(5) 0.7619(5) 0.0612(16) Uiso 0.624(6) 1 d P A 1
H5AA H 0.5248 1.0645 0.7263 0.073 Uiso 0.624(6) 1 calc PR A 1
O1B O 0.7281(7) 0.8592(5) 0.8465(5) 0.053(2) Uiso 0.376(6) 1 d P A 2
C2B C 0.5638(12) 0.8912(7) 0.8033(8) 0.060(3) Uiso 0.376(6) 1 d P A 2
H2BA H 0.5037 0.8342 0.7648 0.072 Uiso 0.376(6) 1 calc PR A 2
C3B C 0.4981(13) 0.9210(8) 0.9072(10) 0.073(3) Uiso 0.376(6) 1 d P A 2
H3BA H 0.4930 0.8619 0.9512 0.110 Uiso 0.376(6) 1 calc PR A 2
H3BB H 0.3959 0.9493 0.8827 0.110 Uiso 0.376(6) 1 calc PR A 2
H3BC H 0.5657 0.9700 0.9510 0.110 Uiso 0.376(6) 1 calc PR A 2
C5B C 0.5752(13) 0.9716(8) 0.7208(8) 0.068(3) Uiso 0.376(6) 1 d P A 2
H5BB H 0.4905 0.9998 0.6712 0.082 Uiso 0.376(6) 1 calc PR A 2
C6 C 0.7293(4) 0.9985(3) 0.7281(3) 0.0602(9) Uani 1 1 d . A .
O2 O 0.7883(3) 1.04228(15) 0.65113(19) 0.0621(7) Uani 1 1 d . . .
C7 C 0.6809(5) 1.1099(3) 0.5781(4) 0.0836(13) Uani 1 1 d . A .
H7A H 0.5863 1.0737 0.5443 0.100 Uiso 1 1 calc R . .
H7B H 0.6534 1.1657 0.6207 0.100 Uiso 1 1 calc R . .
C8 C 0.7517(5) 1.1476(3) 0.4941(4) 0.0951(14) Uani 1 1 d . . .
H8A H 0.6811 1.1927 0.4466 0.143 Uiso 1 1 calc R A .
H8B H 0.7767 1.0923 0.4512 0.143 Uiso 1 1 calc R . .
H8C H 0.8452 1.1834 0.5279 0.143 Uiso 1 1 calc R . .
C9 C 1.0512(4) 0.8401(2) 0.8924(3) 0.0525(9) Uani 1 1 d . . .
C10 C 1.0580(5) 0.8532(3) 1.0029(3) 0.0734(11) Uani 1 1 d . A .
H10A H 0.9999 0.9043 1.0255 0.088 Uiso 1 1 calc R . .
C11 C 1.1505(6) 0.7913(4) 1.0820(4) 0.0990(16) Uani 1 1 d . . .
H11A H 1.1538 0.8018 1.1567 0.119 Uiso 1 1 calc R A .
C12 C 1.2345(6) 0.7169(4) 1.0523(5) 0.107(2) Uani 1 1 d . A .
H12A H 1.2949 0.6761 1.1067 0.128 Uiso 1 1 calc R . .
C13 C 1.2334(4) 0.6992(3) 0.9400(5) 0.0784(13) Uani 1 1 d . . .
C14 C 1.1400(4) 0.7634(2) 0.8574(3) 0.0577(10) Uani 1 1 d . A .
C15 C 1.1408(4) 0.7468(2) 0.7461(4) 0.0682(11) Uani 1 1 d . . .
H15A H 1.0811 0.7882 0.6920 0.082 Uiso 1 1 calc R A .
C16 C 1.2280(4) 0.6703(3) 0.7146(5) 0.0925(14) Uani 1 1 d . A .
H16A H 1.2272 0.6599 0.6402 0.111 Uiso 1 1 calc R . .
C17 C 1.3191(5) 0.6076(3) 0.7983(7) 0.116(2) Uani 1 1 d . . .
H17A H 1.3782 0.5556 0.7785 0.139 Uiso 1 1 calc R A .
C18 C 1.3204(6) 0.6233(4) 0.9053(7) 0.119(2) Uani 1 1 d . A .
H18A H 1.3818 0.5818 0.9584 0.143 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'
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
C1 N1 C9 121.8(3) . . ?
N1 C1 O1A 124.7(3) . . ?
N1 C1 O1B 119.9(3) . . ?
O1A C1 O1B 35.7(2) . . ?
N1 C1 C6 127.5(3) . . ?
O1A C1 C6 106.3(3) . . ?
O1B C1 C6 108.2(3) . . ?
C1 O1A C2A 109.3(3) . . ?
C5A C2A O1A 103.9(5) . . ?
C5A C2A C3A 115.4(5) . . ?
O1A C2A C3A 108.3(5) . . ?
C5A C2A H2AA 109.7 . . ?
O1A C2A H2AA 109.7 . . ?
C3A C2A H2AA 109.7 . . ?
C2A C3A H3AA 109.5 . . ?
C2A C3A H3AB 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
C2A C3A H3AC 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
C6 C5A C2A 109.8(5) . . ?
C6 C5A H5AA 125.1 . . ?
C2A C5A H5AA 125.1 . . ?
C1 O1B C2B 108.3(5) . . ?
O1B C2B C5B 103.6(8) . . ?
O1B C2B C3B 106.7(7) . . ?
C5B C2B C3B 118.3(8) . . ?
O1B C2B H2BA 109.3 . . ?
C5B C2B H2BA 109.3 . . ?
C3B C2B H2BA 109.3 . . ?
C2B C3B H3BA 109.5 . . ?
C2B C3B H3BB 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
C2B C3B H3BC 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?
C6 C5B C2B 110.9(8) . . ?
C6 C5B H5BB 124.6 . . ?
C2B C5B H5BB 124.6 . . ?
C5A C6 O2 129.7(4) . . ?
C5A C6 C5B 35.3(4) . . ?
O2 C6 C5B 127.4(5) . . ?
C5A C6 C1 110.6(4) . . ?
O2 C6 C1 118.4(3) . . ?
C5B C6 C1 108.0(5) . . ?
C6 O2 C7 114.2(3) . . ?
C8 C7 O2 109.7(3) . . ?
C8 C7 H7A 109.7 . . ?
O2 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
O2 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 119.9(3) . . ?
C10 C9 N1 122.5(3) . . ?
C14 C9 N1 117.4(3) . . ?
C9 C10 C11 121.0(4) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C12 C11 C10 121.0(5) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C11 C12 C13 121.1(4) . . ?
C11 C12 H12A 119.5 . . ?
C13 C12 H12A 119.5 . . ?
C18 C13 C12 123.1(5) . . ?
C18 C13 C14 118.3(5) . . ?
C12 C13 C14 118.6(4) . . ?
C15 C14 C9 123.0(3) . . ?
C15 C14 C13 118.5(4) . . ?
C9 C14 C13 118.5(4) . . ?
C16 C15 C14 121.6(4) . . ?
C16 C15 H15A 119.2 . . ?
C14 C15 H15A 119.2 . . ?
C15 C16 C17 118.7(5) . . ?
C15 C16 H16A 120.7 . . ?
C17 C16 H16A 120.7 . . ?
C18 C17 C16 120.4(5) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C17 C18 C13 122.5(5) . . ?
C17 C18 H18A 118.7 . . ?
C13 C18 H18A 118.7 . . ?
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
N1 C1 1.247(4) . ?
N1 C9 1.424(4) . ?
C1 O1A 1.378(5) . ?
C1 O1B 1.448(6) . ?
C1 C6 1.461(5) . ?
O1A C2A 1.475(6) . ?
C2A C5A 1.464(8) . ?
C2A C3A 1.477(9) . ?
C2A H2AA 0.9800 . ?
C3A H3AA 0.9600 . ?
C3A H3AB 0.9600 . ?
C3A H3AC 0.9600 . ?
C5A C6 1.316(6) . ?
C5A H5AA 0.9300 . ?
O1B C2B 1.488(11) . ?
C2B C5B 1.494(13) . ?
C2B C3B 1.579(16) . ?
C2B H2BA 0.9800 . ?
C3B H3BA 0.9600 . ?
C3B H3BB 0.9600 . ?
C3B H3BC 0.9600 . ?
C5B C6 1.389(11) . ?
C5B H5BB 0.9300 . ?
C6 O2 1.321(4) . ?
O2 C7 1.458(4) . ?
C7 C8 1.421(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.367(5) . ?
C9 C14 1.410(5) . ?
C10 C11 1.389(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.334(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.409(7) . ?
C12 H12A 0.9300 . ?
C13 C18 1.392(8) . ?
C13 C14 1.435(5) . ?
C14 C15 1.398(5) . ?
C15 C16 1.381(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.423(8) . ?
C16 H16A 0.9300 . ?
C17 C18 1.338(7) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190608
