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#$Date: 2022-09-14 17:31:13 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277831 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/10/05/1100584.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_1100584
loop_
_publ_author_name
'Bach, Thorsten'
'Bergmann, Hermann'
'Harms, Klaus'
_publ_contact_author
;
        Thorsten Bach
        Fachbereich Chemie der Universität
        Philipps Universität Marburg
        Hans-Meerwein-Str.
        35032 Marburg
        Bundesrepublik Deutschland
;
_publ_contact_author_fax         '+49 6421 288917 '
_publ_contact_author_phone       '+49 6421 285562 '
_publ_section_title
;
 High Facial Diastereoselectivity in the Photocycloaddition of a Chiral
 Aromatic Aldehyde and an Enamide Induced by Intermolecular Hydrogen Bonding
;
_journal_coden_ASTM              JACSAT
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10650
_journal_page_last               10651
_journal_paper_doi               10.1021/ja992209m
_journal_volume                  121
_journal_year                    1999
_chemical_formula_sum            'C24 H30 N2 O5'
_chemical_formula_weight         426.50
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_cell_angle_alpha                105.19(1)
_cell_angle_beta                 106.46(1)
_cell_angle_gamma                101.38(1)
_cell_formula_units_Z            2
_cell_length_a                   8.145(1)
_cell_length_b                   11.170(1)
_cell_length_c                   13.241(1)
_cell_measurement_temperature    223(2)
_cell_volume                     1065.85(18)
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4207
_diffrn_reflns_theta_full        69.87
_diffrn_reflns_theta_max         69.87
_diffrn_reflns_theta_min         3.70
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  0.9280
_exptl_absorpt_correction_T_min  0.7264
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0483
_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)+(0.0494P)²+0.3315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                2872
_reflns_number_total             4021
_reflns_threshold_expression     >2sigma(I)
_cod_database_code               1100584
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -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
N1 N 0.5385(2) 0.86450(19) 0.62770(17) 0.0378(5) Uani 1 1 d . . .
H1A H 0.629(4) 0.934(3) 0.662(2) 0.056(8) Uiso 1 1 d . . .
N2 N 0.8650(3) 1.0807(2) 0.92203(17) 0.0400(5) Uani 1 1 d . . .
H2A H 0.793(4) 1.001(3) 0.886(2) 0.055(8) Uiso 1 1 d . . .
O1 O 0.5805(2) 0.83588(15) 0.79451(14) 0.0437(4) Uani 1 1 d . . .
O2 O 0.23642(19) 0.97177(13) 0.73426(12) 0.0347(4) Uani 1 1 d . . .
O3 O 0.2528(2) 1.00943(14) 0.57776(13) 0.0396(4) Uani 1 1 d . . .
O4 O 0.9014(2) 1.33484(15) 1.11922(14) 0.0477(4) Uani 1 1 d . . .
O5 O 0.8610(2) 1.09973(17) 0.75673(14) 0.0514(5) Uani 1 1 d . . .
C1 C 0.2996(3) 0.7068(2) 0.45007(18) 0.0337(5) Uani 1 1 d . . .
C2 C 0.4664(3) 0.8244(2) 0.50524(19) 0.0385(5) Uani 1 1 d . . .
H2B H 0.5595 0.8041 0.4763 0.046 Uiso 1 1 calc R . .
H2C H 0.4370 0.8974 0.4839 0.046 Uiso 1 1 calc R . .
C4 C 0.4978(3) 0.7978(2) 0.6917(2) 0.0346(5) Uani 1 1 d . . .
C5 C 0.3406(3) 0.6728(2) 0.63462(18) 0.0336(5) Uani 1 1 d . . .
C6 C 0.1636(3) 0.7044(2) 0.63276(18) 0.0328(5) Uani 1 1 d . . .
H6A H 0.0673 0.6224 0.6028 0.039 Uiso 1 1 calc R . .
H6B H 0.1741 0.7468 0.7101 0.039 Uiso 1 1 calc R . .
C7 C 0.1080(3) 0.79106(19) 0.56460(18) 0.0303(5) Uani 1 1 d . . .
C8 C 0.1261(3) 0.7417(2) 0.44982(18) 0.0340(5) Uani 1 1 d . . .
H8A H 0.1171 0.8084 0.4147 0.041 Uiso 1 1 calc R . .
H8B H 0.0245 0.6646 0.4027 0.041 Uiso 1 1 calc R . .
C9 C 0.3282(3) 0.6127(2) 0.51376(19) 0.0380(5) Uani 1 1 d . . .
H9A H 0.4387 0.5907 0.5133 0.046 Uiso 1 1 calc R . .
H9B H 0.2284 0.5325 0.4766 0.046 Uiso 1 1 calc R . .
C10 C 0.2818(4) 0.6457(2) 0.3281(2) 0.0494(6) Uani 1 1 d . . .
H10A H 0.3868 0.6181 0.3258 0.074 Uiso 1 1 calc R . .
H10B H 0.2717 0.7092 0.2905 0.074 Uiso 1 1 calc R . .
H10C H 0.1758 0.5713 0.2907 0.074 Uiso 1 1 calc R . .
C11 C 0.3716(3) 0.5807(2) 0.7005(2) 0.0449(6) Uani 1 1 d . . .
H11A H 0.3773 0.6211 0.7763 0.067 Uiso 1 1 calc R . .
H11B H 0.4835 0.5617 0.7024 0.067 Uiso 1 1 calc R . .
H11C H 0.2738 0.5007 0.6647 0.067 Uiso 1 1 calc R . .
C12 C -0.0882(3) 0.7868(2) 0.5498(2) 0.0394(5) Uani 1 1 d . . .
H12A H -0.1245 0.8420 0.5075 0.059 Uiso 1 1 calc R . .
H12B H -0.0986 0.8174 0.6228 0.059 Uiso 1 1 calc R . .
H12C H -0.1648 0.6984 0.5099 0.059 Uiso 1 1 calc R . .
C13 C 0.2102(3) 0.9346(2) 0.62253(18) 0.0309(5) Uani 1 1 d . . .
C14 C 0.3471(3) 1.0969(2) 0.80398(18) 0.0331(5) Uani 1 1 d . . .
C15 C 0.4850(3) 1.1005(2) 0.89402(18) 0.0349(5) Uani 1 1 d . . .
H15A H 0.4984 1.0228 0.9053 0.042 Uiso 1 1 calc R . .
C16 C 0.6049(3) 1.2186(2) 0.96856(18) 0.0349(5) Uani 1 1 d . . .
C17 C 0.5816(3) 1.3324(2) 0.9515(2) 0.0397(6) Uani 1 1 d . . .
H17A H 0.6621 1.4129 1.0009 0.048 Uiso 1 1 calc R . .
C18 C 0.4388(3) 1.3271(2) 0.8610(2) 0.0415(6) Uani 1 1 d . . .
H18A H 0.4225 1.4046 0.8506 0.050 Uiso 1 1 calc R . .
C19 C 0.3206(3) 1.2094(2) 0.7862(2) 0.0394(5) Uani 1 1 d . . .
H19A H 0.2247 1.2060 0.7248 0.047 Uiso 1 1 calc R . .
C20 C 0.7530(3) 1.2156(2) 1.06377(19) 0.0420(6) Uani 1 1 d . . .
H20A H 0.7056 1.1910 1.1189 0.050 Uiso 1 1 calc R . .
C21 C 0.8822(3) 1.1359(2) 1.0374(2) 0.0432(6) Uani 1 1 d . . .
H21A H 0.8895 1.0721 1.0770 0.052 Uiso 1 1 calc R . .
C22 C 1.0323(3) 1.2654(2) 1.1037(2) 0.0488(6) Uani 1 1 d . . .
H22A H 1.1112 1.2642 1.1755 0.059 Uiso 1 1 calc R . .
C23 C 0.9068(3) 1.1504(2) 0.8593(2) 0.0399(6) Uani 1 1 d . . .
C24 C 1.0130(3) 1.2905(2) 0.9204(2) 0.0427(6) Uani 1 1 d . . .
H24A H 0.9303 1.3430 0.9241 0.051 Uiso 1 1 calc R . .
H24B H 1.0849 1.3189 0.8783 0.051 Uiso 1 1 calc R . .
C25 C 1.1364(3) 1.3137(3) 1.0387(2) 0.0499(7) Uani 1 1 d . . .
H25A H 1.2277 1.2689 1.0353 0.060 Uiso 1 1 calc R . .
H25B H 1.1975 1.4068 1.0766 0.060 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_radius_bond
C 0.68
H 0.23
N 0.68
O 0.68
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 C4 1.333(3) . ?
N1 C2 1.466(3) . ?
N1 H1A 0.87(3) . ?
N2 C23 1.344(3) . ?
N2 C21 1.444(3) . ?
N2 H2A 0.88(3) . ?
O1 C4 1.245(3) . ?
O2 C13 1.368(3) . ?
O2 C14 1.405(2) . ?
O3 C13 1.197(2) . ?
O4 C20 1.457(3) . ?
O4 C22 1.465(3) . ?
O5 C23 1.237(3) . ?
C1 C9 1.522(3) . ?
C1 C2 1.528(3) . ?
C1 C10 1.532(3) . ?
C1 C8 1.538(3) . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C4 C5 1.534(3) . ?
C5 C11 1.527(3) . ?
C5 C9 1.530(3) . ?
C5 C6 1.545(3) . ?
C6 C7 1.535(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 C13 1.523(3) . ?
C7 C8 1.535(3) . ?
C7 C12 1.544(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C14 C15 1.372(3) . ?
C14 C19 1.384(3) . ?
C15 C16 1.390(3) . ?
C15 H15A 0.9400 . ?
C16 C17 1.387(3) . ?
C16 C20 1.490(3) . ?
C17 C18 1.392(3) . ?
C17 H17A 0.9400 . ?
C18 C19 1.384(3) . ?
C18 H18A 0.9400 . ?
C19 H19A 0.9400 . ?
C20 C21 1.561(3) . ?
C20 H20A 0.9900 . ?
C21 C22 1.545(3) . ?
C21 H21A 0.9900 . ?
C22 C25 1.493(4) . ?
C22 H22A 0.9900 . ?
C23 C24 1.502(3) . ?
C24 C25 1.524(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O5 0.87(3) 2.15(3) 3.017(3) 176(2) .
N2 H2A O1 0.88(3) 2.06(3) 2.926(3) 167(2) .
