#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/05/7110521.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_7110521
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 H21 N O2'
_chemical_formula_weight         247.33
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.546(1)
_cell_length_b                   11.848(1)
_cell_length_c                   15.712(1)
_cell_measurement_temperature    293(2)
_cell_volume                     1404.7(2)
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3096
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         .145
_refine_diff_density_min         -.124
_refine_diff_density_rms         .032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.96(175)
_refine_ls_extinction_coef       0.0201(35)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²l³/sin(2q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.011
_refine_ls_goodness_of_fit_obs   1.133
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_restrained_S_obs      1.133
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_obs          0.0502
_refine_ls_shift/esd_max         -1.823
_refine_ls_shift/esd_mean        0.160
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[s²(Fo²)+( 0.0605P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1158
_refine_ls_wR_factor_obs         0.0990
_reflns_number_observed          1942
_reflns_number_total             3096
_reflns_observed_criterion       2sigma(I)
_cod_data_source_file            901723bsup1.cif
_cod_data_source_block           2d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w=1/[s^2^(Fo^2^)+(
0.0605P)^2^+0.0000P] 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^)+( 0.0605P)^2^+0.0000P] where
P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               7110521
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
O1 O 0.0939(2) 0.34652(11) 0.68425(11) 0.0458(4) Uani 1 d
N2 N -0.2595(2) 0.3745(2) 0.68040(15) 0.0491(6) Uani 1 d
C3 C 0.0390(2) 0.2267(2) 0.80710(15) 0.0379(5) Uani 1 d
O4 O -0.5438(2) 0.3268(2) 0.6946(2) 0.0784(7) Uani 1 d
C5 C -0.0066(3) 0.1247(2) 0.8454(2) 0.0432(6) Uani 1 d
C6 C 0.0044(3) 0.2486(2) 0.71413(14) 0.0381(5) Uani 1 d
C7 C -0.1905(3) 0.2610(2) 0.6845(2) 0.0417(6) Uani 1 d
C8 C 0.0893(3) 0.1896(2) 0.9835(2) 0.0509(7) Uani 1 d
C9 C -0.4315(3) 0.3999(2) 0.6838(2) 0.0521(6) Uani 1 d
C10 C 0.1330(4) 0.2909(2) 0.9452(2) 0.0578(8) Uani 1 d
C11 C 0.1105(3) 0.3088(2) 0.8598(2) 0.0516(7) Uani 1 d
C12 C -0.1444(3) 0.1981(2) 0.6023(2) 0.0493(6) Uani 1 d
C13 C 0.0189(3) 0.1068(2) 0.9310(2) 0.0488(6) Uani 1 d
C14 C 0.0182(3) 0.1500(2) 0.6488(2) 0.0468(6) Uani 1 d
C15 C 0.1891(4) 0.1320(3) 0.5997(2) 0.0676(8) Uani 1 d
C16 C 0.1108(6) 0.1714(4) 1.0776(2) 0.0732(9) Uani 1 d
C17 C -0.2785(5) 0.1170(3) 0.5644(3) 0.0728(9) Uani 1 d
C18 C -0.4774(5) 0.5226(3) 0.6740(3) 0.0789(11) Uani 1 d
H1 H -0.2684(31) 0.2195(17) 0.7195(14) 0.038(6) Uiso 1 d
H2 H -0.0577(30) 0.0690(19) 0.8097(14) 0.046(6) Uiso 1 d
H3 H -0.0185(31) 0.0813(20) 0.6764(14) 0.050(7) Uiso 1 d
H4 H 0.2812(59) 0.1045(30) 0.6388(25) 0.113(13) Uiso 1 d
H5 H -0.0045(31) 0.0346(21) 0.9551(15) 0.047(7) Uiso 1 d
H6 H 0.2308(47) 0.2032(29) 0.5797(23) 0.092(11) Uiso 1 d
H7 H 0.1070(67) 0.1025(41) 1.0888(28) 0.145(19) Uiso 1 d
H8 H -0.1154(35) 0.2533(20) 0.5591(16) 0.056(7) Uiso 1 d
H9 H 0.1465(33) 0.3790(22) 0.8362(15) 0.058(7) Uiso 1 d
H10 H 0.2241(89) 0.1695(45) 1.0964(41) 0.180(24) Uiso 1 d
H11 H -0.2194(64) 0.0839(34) 0.5142(29) 0.135(17) Uiso 1 d
H12 H 0.1674(54) 0.0716(31) 0.5565(26) 0.115(13) Uiso 1 d
H13 H -0.1788(34) 0.4272(19) 0.6703(14) 0.046(7) Uiso 1 d
H14 H 0.1856(40) 0.3468(22) 0.9802(18) 0.066(8) Uiso 1 d
H15 H -0.3125(44) 0.0568(28) 0.6103(22) 0.092(11) Uiso 1 d
H16 H -0.3779(48) 0.1551(24) 0.5447(20) 0.081(10) Uiso 1 d
H17 H -0.5599(74) 0.5294(43) 0.6301(34) 0.159(22) Uiso 1 d
H18 H -0.3819(64) 0.5704(34) 0.6706(26) 0.128(16) Uiso 1 d
H19 H 0.0666(84) 0.2414(51) 1.1187(34) 0.209(23) Uiso 1 d
H20 H 0.2095(44) 0.3356(22) 0.6889(21) 0.077(9) Uiso 1 d
H24 H -0.5759(58) 0.5357(33) 0.7040(29) 0.132(15) 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
C9 N2 C7 124.1(2)
C11 C3 C5 116.5(2)
C11 C3 C6 121.7(2)
C5 C3 C6 121.7(2)
C13 C5 C3 121.4(2)
O1 C6 C3 112.2(2)
O1 C6 C7 105.9(2)
C3 C6 C7 118.1(2)
O1 C6 C14 111.3(2)
C3 C6 C14 119.8(2)
C7 C6 C14 86.4(2)
N2 C7 C6 116.4(2)
N2 C7 C12 119.8(2)
C6 C7 C12 89.5(2)
C13 C8 C10 116.5(3)
C13 C8 C16 121.7(3)
C10 C8 C16 121.8(3)
O4 C9 N2 121.3(2)
O4 C9 C18 122.7(2)
N2 C9 C18 116.1(2)
C11 C10 C8 122.1(3)
C10 C11 C3 121.7(2)
C17 C12 C14 118.9(2)
C17 C12 C7 119.2(3)
C14 C12 C7 87.7(2)
C5 C13 C8 121.7(2)
C12 C14 C15 119.2(2)
C12 C14 C6 88.9(2)
C15 C14 C6 119.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.422(3)
N2 C9 1.334(3)
N2 C7 1.443(3)
C3 C11 1.387(3)
C3 C5 1.393(3)
C3 C6 1.506(3)
O4 C9 1.224(3)
C5 C13 1.374(3)
C6 C7 1.549(3)
C6 C14 1.558(3)
C7 C12 1.531(4)
C8 C13 1.388(3)
C8 C10 1.383(3)
C8 C16 1.504(4)
C9 C18 1.502(4)
C10 C11 1.369(4)
C12 C17 1.517(4)
C12 C14 1.538(3)
C14 C15 1.518(4)
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
C11 C3 C5 C13 -0.3(3)
C6 C3 C5 C13 -177.4(2)
C11 C3 C6 O1 15.5(3)
C5 C3 C6 O1 -167.4(2)
C11 C3 C6 C7 -108.2(2)
C5 C3 C6 C7 68.9(3)
C11 C3 C6 C14 148.9(2)
C5 C3 C6 C14 -34.1(3)
C9 N2 C7 C6 -157.3(2)
C9 N2 C7 C12 96.9(3)
O1 C6 C7 N2 -32.6(3)
C3 C6 C7 N2 94.1(3)
C14 C6 C7 N2 -143.7(2)
O1 C6 C7 C12 90.8(2)
C3 C6 C7 C12 -142.4(2)
C14 C6 C7 C12 -20.3(2)
C7 N2 C9 O4 3.3(4)
C7 N2 C9 C18 -177.0(3)
C13 C8 C10 C11 -0.8(4)
C16 C8 C10 C11 -178.7(3)
C8 C10 C11 C3 1.3(4)
C5 C3 C11 C10 -0.8(4)
C6 C3 C11 C10 176.4(2)
N2 C7 C12 C17 -96.7(3)
C6 C7 C12 C17 142.8(2)
N2 C7 C12 C14 141.1(2)
C6 C7 C12 C14 20.6(2)
C3 C5 C13 C8 0.8(4)
C10 C8 C13 C5 -0.2(4)
C16 C8 C13 C5 177.6(3)
C17 C12 C14 C15 93.1(4)
C7 C12 C14 C15 -144.4(3)
C17 C12 C14 C6 -142.9(3)
C7 C12 C14 C6 -20.5(2)
O1 C6 C14 C12 -85.4(2)
C3 C6 C14 C12 140.8(2)
C7 C6 C14 C12 20.2(2)
O1 C6 C14 C15 38.1(3)
C3 C6 C14 C15 -95.7(3)
C7 C6 C14 C15 143.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 15529143
