#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/05/7110519.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7110519
loop_
_publ_author_name
'Griesbeck, Axel G.'
'Heckroth, Heike'
'Lex, Johann'
_publ_section_title
;
 Stereoselective Yang cyclizations of α-amido ketones
;
_journal_issue                   12
_journal_name_full               'Chemical Communications'
_journal_page_first              1109
_journal_paper_doi               10.1039/a901723b
_journal_year                    1999
_chemical_formula_moiety         'C15 H21 N O2'
_chemical_formula_sum            'C15 H22 N O2.5'
_chemical_formula_weight         256.34
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.62(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.840(1)
_cell_length_b                   18.077(1)
_cell_length_c                   12.920(1)
_cell_measurement_temperature    293(2)
_cell_volume                     2998.7(4)
_computing_cell_refinement       'nonius denzo'
_computing_data_collection       'nonius collect'
_computing_data_reduction        'nonius denzo'
_computing_molecular_graphics    xtal
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'nonius kappa-ccd diffractometer'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11448
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_description       prism
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         .170
_refine_diff_density_min         -.154
_refine_diff_density_rms         .036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.029
_refine_ls_goodness_of_fit_obs   1.221
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_restrained_S_obs      1.221
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_obs          0.0581
_refine_ls_shift/esd_max         0.652
_refine_ls_shift/esd_mean        0.072
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[s²(Fo²)+( 0.0619P)²+0.5637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1422
_refine_ls_wR_factor_obs         0.1175
_reflns_number_observed          1748
_reflns_number_total             3199
_reflns_observed_criterion       2sigma(I)
_cod_data_source_file            901723bsup1.cif
_cod_data_source_block           2b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w=1/[s^2^(Fo^2^)+(
0.0619P)^2^+0.5637P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'.
New tag '_refine_ls_weighting_details' was created. The value of the
new tag was set to 'w=1/[s^2^(Fo^2^)+( 0.0619P)^2^+0.5637P] where
P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C15 H22 N O2.50'
_cod_database_code               7110519
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'
'-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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C -0.1020(2) 0.4086(2) 1.0221(3) 0.0670(8) Uani 1 d .
H1A H -0.1358(36) 0.3878(26) 1.0737(37) 0.166(19) Uiso 1 d .
H1B H -0.1359(28) 0.4056(18) 0.9650(30) 0.121(13) Uiso 1 d .
H1C H -0.1107(36) 0.4561(31) 1.0560(39) 0.192(20) Uiso 1 d .
C2 C 0.0095(2) 0.38626(11) 1.0157(2) 0.0459(5) Uani 1 d .
N3 N 0.03934(15) 0.35376(10) 0.92725(14) 0.0460(5) Uani 1 d .
H3 H -0.0072(20) 0.3542(14) 0.8775(21) 0.073(8) Uiso 1 d .
C4 C 0.1449(2) 0.33375(11) 0.9053(2) 0.0424(5) Uani 1 d .
H4 H 0.1841(14) 0.3350(9) 0.9708(14) 0.034(5) Uiso 1 d .
C5 C 0.2020(2) 0.37813(11) 0.82001(14) 0.0396(5) Uani 1 d .
O6 O 0.12901(12) 0.39497(9) 0.73903(10) 0.0467(4) Uani 1 d .
C7 C 0.2572(2) 0.30376(11) 0.7893(2) 0.0475(6) Uani 1 d .
C8 C 0.3607(2) 0.2934(2) 0.8465(2) 0.0633(7) Uani 1 d .
H8A H 0.3822(20) 0.2448(16) 0.8361(18) 0.072(8) Uiso 1 d .
H8B H 0.3581(18) 0.3024(13) 0.9236(21) 0.073(8) Uiso 1 d .
H8C H 0.4124(21) 0.3284(16) 0.8199(19) 0.084(9) Uiso 1 d .
C9 C 0.2704(3) 0.2891(2) 0.6743(2) 0.0689(8) Uani 1 d .
H9A H 0.2020(27) 0.2937(17) 0.6328(23) 0.108(11) Uiso 1 d .
H9B H 0.2989(22) 0.2383(18) 0.6635(20) 0.095(9) Uiso 1 d .
H9C H 0.3234(23) 0.3233(17) 0.6484(21) 0.099(10) Uiso 1 d .
C10 C 0.1676(2) 0.26270(13) 0.8436(2) 0.0525(6) Uani 1 d .
H10A H 0.1889(15) 0.2181(12) 0.8824(15) 0.049(6) Uiso 1 d .
H10B H 0.1057(18) 0.2525(12) 0.7964(17) 0.058(7) Uiso 1 d .
C11 C 0.2658(2) 0.44529(11) 0.84795(15) 0.0410(5) Uani 1 d .
C12 C 0.2904(2) 0.49759(14) 0.7734(2) 0.0621(7) Uani 1 d .
H12 H 0.2623(17) 0.4924(12) 0.7091(18) 0.059(7) Uiso 1 d .
C13 C 0.3490(2) 0.5590(2) 0.7976(2) 0.0732(8) Uani 1 d .
H13 H 0.3617(20) 0.5943(15) 0.7492(20) 0.079(8) Uiso 1 d .
C14 C 0.3865(2) 0.57163(13) 0.8964(2) 0.0559(6) Uani 1 d .
C15 C 0.4501(3) 0.6398(2) 0.9229(4) 0.0857(10) Uani 1 d .
H15A H 0.4838(32) 0.6372(21) 0.9839(32) 0.138(16) Uiso 1 d .
H15B H 0.4054(39) 0.6814(30) 0.9308(37) 0.188(22) Uiso 1 d .
H15C H 0.5020(44) 0.6441(31) 0.8818(46) 0.206(25) Uiso 1 d .
C16 C 0.3621(2) 0.52040(13) 0.9705(2) 0.0541(6) Uani 1 d .
H16 H 0.3892(17) 0.5292(12) 1.0424(18) 0.059(6) Uiso 1 d .
C17 C 0.3024(2) 0.45907(13) 0.9476(2) 0.0503(6) Uani 1 d .
H17 H 0.2880(16) 0.4260(12) 0.9987(16) 0.050(6) Uiso 1 d .
O18 O 0.07144(13) 0.39727(9) 1.08786(11) 0.0603(5) Uani 1 d .
OW O 0.0000 0.51769(12) 0.7500 0.0502(6) Uani 1 d S
HO6 H 0.0929(21) 0.4355(15) 0.7544(18) 0.076(9) Uiso 1 d .
HW H -0.0261(23) 0.5467(16) 0.7990(20) 0.099(10) Uiso 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
O18 C2 N3 121.6(2)
O18 C2 C1 121.8(2)
N3 C2 C1 116.6(2)
C2 N3 C4 123.9(2)
N3 C4 C10 119.8(2)
N3 C4 C5 117.7(2)
C10 C4 C5 88.3(2)
O6 C5 C11 110.7(2)
O6 C5 C4 108.6(2)
C11 C5 C4 120.4(2)
O6 C5 C7 106.92(15)
C11 C5 C7 120.3(2)
C4 C5 C7 87.41(14)
C9 C7 C8 110.2(2)
C9 C7 C10 116.9(2)
C8 C7 C10 111.8(2)
C9 C7 C5 116.8(2)
C8 C7 C5 112.1(2)
C10 C7 C5 87.5(2)
C4 C10 C7 88.9(2)
C17 C11 C12 116.4(2)
C17 C11 C5 123.0(2)
C12 C11 C5 120.7(2)
C13 C12 C11 121.3(2)
C12 C13 C14 121.9(2)
C16 C14 C13 117.0(2)
C16 C14 C15 121.2(3)
C13 C14 C15 121.7(3)
C14 C16 C17 121.7(2)
C16 C17 C11 121.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.490(4)
C2 O18 1.235(2)
C2 N3 1.345(3)
N3 C4 1.434(3)
C4 C10 1.541(3)
C4 C5 1.553(3)
C5 O6 1.430(2)
C5 C11 1.506(3)
C5 C7 1.572(3)
C7 C9 1.521(3)
C7 C8 1.525(3)
C7 C10 1.544(3)
C11 C17 1.388(3)
C11 C12 1.388(3)
C12 C13 1.376(4)
C13 C14 1.379(3)
C14 C16 1.370(3)
C14 C15 1.515(4)
C16 C17 1.378(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O18 C2 N3 C4 -4.4(3)
C1 C2 N3 C4 175.3(2)
C2 N3 C4 C10 144.1(2)
C2 N3 C4 C5 -110.7(2)
N3 C4 C5 O6 -37.0(2)
C10 C4 C5 O6 86.1(2)
N3 C4 C5 C11 92.0(2)
C10 C4 C5 C11 -144.9(2)
N3 C4 C5 C7 -144.0(2)
C10 C4 C5 C7 -20.9(2)
O6 C5 C7 C9 31.3(3)
C11 C5 C7 C9 -96.0(3)
C4 C5 C7 C9 139.9(2)
O6 C5 C7 C8 159.8(2)
C11 C5 C7 C8 32.5(3)
C4 C5 C7 C8 -91.6(2)
O6 C5 C7 C10 -87.7(2)
C11 C5 C7 C10 145.0(2)
C4 C5 C7 C10 20.9(2)
N3 C4 C10 C7 142.6(2)
C5 C4 C10 C7 21.3(2)
C9 C7 C10 C4 -140.0(2)
C8 C7 C10 C4 91.8(2)
C5 C7 C10 C4 -21.1(2)
O6 C5 C11 C17 147.3(2)
C4 C5 C11 C17 19.2(3)
C7 C5 C11 C17 -87.1(2)
O6 C5 C11 C12 -32.2(3)
C4 C5 C11 C12 -160.3(2)
C7 C5 C11 C12 93.4(2)
C17 C11 C12 C13 0.8(4)
C5 C11 C12 C13 -179.7(2)
C11 C12 C13 C14 0.3(5)
C12 C13 C14 C16 -0.6(4)
C12 C13 C14 C15 -179.4(3)
C13 C14 C16 C17 -0.2(4)
C15 C14 C16 C17 178.5(3)
C14 C16 C17 C11 1.4(4)
C12 C11 C17 C16 -1.6(3)
C5 C11 C17 C16 178.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139183744
