#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/46/1504665.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_1504665
loop_
_publ_author_name
'Hong, Bor-Cherng'
'Nimje, Roshan Y.'
'Sadani, Amit A.'
'Liao, Ju-Hsiou'
_publ_section_title
;
 Organocatalytic enantioselective domino Michael-aldol condensation of
 5-oxoalkanal and alpha,beta-unsaturated aldehydes. Efficient assembly of
 densely functionalized cyclohexenes.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2345
_journal_page_last               2348
_journal_paper_doi               10.1021/ol8005369
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration unk
_chemical_formula_sum            'C15 H15 N O4'
_chemical_formula_weight         273.28
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   7.2909(13)
_cell_length_b                   7.3802(13)
_cell_length_c                   25.433(5)
_cell_measurement_reflns_used    329
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.529
_cell_measurement_theta_min      -23.529
_cell_volume                     1368.5(4)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    Ortep-3
_computing_publication_material  'Wingx publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       'phi-omega scan'
_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  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8807
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0755
_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)+(0.0439P)²+0.7807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1496
_reflns_number_gt                1472
_reflns_number_total             1928
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8005369-file001.cif
_cod_data_source_block           ryn-02-22
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1504665
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.9183(7) 1.0235(6) -0.00664(17) 0.0498(12) Uani 1 1 d .
H1 H 0.9082 1.0823 -0.0389 0.060 Uiso 1 1 calc R
C2 C 1.0706(7) 1.0493(6) 0.02419(17) 0.0457(11) Uani 1 1 d .
H2 H 1.1653 1.1246 0.0131 0.055 Uiso 1 1 calc R
C3 C 1.0803(6) 0.9609(5) 0.07206(15) 0.0348(9) Uani 1 1 d .
C4 C 0.9449(5) 0.8460(5) 0.09064(14) 0.0287(8) Uani 1 1 d .
C5 C 0.7956(6) 0.8232(6) 0.05746(16) 0.0394(10) Uani 1 1 d .
H5 H 0.7019 0.7455 0.0677 0.047 Uiso 1 1 calc R
C6 C 0.7812(7) 0.9107(7) 0.01029(18) 0.0510(13) Uani 1 1 d .
H6 H 0.6777 0.8935 -0.0105 0.061 Uiso 1 1 calc R
C7 C 0.9512(6) 0.7474(5) 0.14369(14) 0.0317(9) Uani 1 1 d .
H7 H 1.0805 0.7279 0.1526 0.038 Uiso 1 1 calc R
C8 C 0.8669(6) 0.8641(6) 0.18729(16) 0.0379(10) Uani 1 1 d .
H8 H 0.9024 0.9897 0.1800 0.045 Uiso 1 1 calc R
C9 C 0.6589(7) 0.8583(7) 0.1866(2) 0.0507(13) Uani 1 1 d .
H9A H 0.6143 0.9078 0.1537 0.061 Uiso 1 1 calc R
H9B H 0.6111 0.9322 0.2150 0.061 Uiso 1 1 calc R
C10 C 0.5911(7) 0.6646(6) 0.1928(2) 0.0613(15) Uani 1 1 d .
H10A H 0.5958 0.6328 0.2297 0.074 Uiso 1 1 calc R
H10B H 0.4637 0.6598 0.1819 0.074 Uiso 1 1 calc R
C11 C 0.6947(6) 0.5269(6) 0.16270(17) 0.0412(10) Uani 1 1 d .
C12 C 0.8598(6) 0.5632(5) 0.14104(14) 0.0318(9) Uani 1 1 d .
C13 C 0.9423(10) 0.8177(6) 0.24051(19) 0.0603(15) Uani 1 1 d .
H13 H 0.8788 0.8619 0.2695 0.072 Uiso 1 1 calc R
C14 C 0.9689(8) 0.4219(7) 0.11571(19) 0.0549(13) Uani 1 1 d .
H14 H 0.9148 0.3092 0.1106 0.066 Uiso 1 1 calc R
C15 C 0.6005(8) 0.3446(6) 0.1612(2) 0.0634(15) Uani 1 1 d .
H15A H 0.6644 0.2662 0.1373 0.095 Uiso 1 1 calc R
H15B H 0.4762 0.3598 0.1496 0.095 Uiso 1 1 calc R
H15C H 0.6012 0.2921 0.1957 0.095 Uiso 1 1 calc R
N1 N 1.2457(5) 0.9996(5) 0.10328(17) 0.0502(10) Uani 1 1 d .
O1 O 1.3887(5) 1.0210(7) 0.07919(16) 0.0847(14) Uani 1 1 d .
O2 O 1.2341(5) 1.0142(5) 0.15054(14) 0.0667(10) Uani 1 1 d .
O3 O 1.0751(7) 0.7301(5) 0.24907(15) 0.0873(15) Uani 1 1 d .
O4 O 1.1230(6) 0.4422(5) 0.10120(16) 0.0776(12) Uani 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C6 C1 C2 119.6(4)
C1 C2 C3 118.6(4)
C2 C3 C4 123.5(4)
C2 C3 N1 115.2(4)
C4 C3 N1 121.3(3)
C3 C4 C5 115.2(3)
C3 C4 C7 124.7(3)
C5 C4 C7 120.1(4)
C6 C5 C4 122.5(4)
C5 C6 C1 120.5(4)
C12 C7 C8 111.1(3)
C12 C7 C4 111.9(3)
C8 C7 C4 110.9(3)
C13 C8 C9 111.7(5)
C13 C8 C7 112.1(4)
C9 C8 C7 112.1(4)
C8 C9 C10 110.5(4)
C11 C10 C9 115.2(4)
C12 C11 C10 122.0(4)
C12 C11 C15 124.8(4)
C10 C11 C15 113.1(4)
C11 C12 C14 121.6(4)
C11 C12 C7 123.5(4)
C14 C12 C7 114.8(4)
O3 C13 C8 126.2(5)
O4 C14 C12 124.1(5)
O2 N1 O1 123.2(4)
O2 N1 C3 119.8(4)
O1 N1 C3 117.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.370(6)
C1 C2 1.373(6)
C2 C3 1.383(6)
C3 C4 1.385(5)
C3 N1 1.471(6)
C4 C5 1.387(5)
C4 C7 1.534(5)
C5 C6 1.366(6)
C7 C12 1.516(5)
C7 C8 1.533(5)
C8 C13 1.501(6)
C8 C9 1.517(6)
C9 C10 1.520(7)
C10 C11 1.479(6)
C11 C12 1.350(6)
C11 C15 1.511(6)
C12 C14 1.461(6)
C13 O3 1.185(6)
C14 O4 1.192(6)
N1 O2 1.210(5)
N1 O1 1.220(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 24938756
