#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/16/4021622.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_4021622
loop_
_publ_author_name
'Horacio F. Olivo'
'Ricardo Tovar-Miranda'
'Efraín Barragán'
_publ_section_title
;
 Synthesis of (-)-Stemoamide Using a Stereoselective anti-Aldol Step
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3287
_journal_page_last               3290
_journal_paper_doi               10.1021/jo052364l
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C17 H12 N O3'
_chemical_formula_weight         278.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 102.121(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3581(7)
_cell_length_b                   6.7810(7)
_cell_length_c                   11.7266(12)
_cell_measurement_temperature    100(2)
_cell_volume                     572.06(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3840
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9524
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             290
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(17)
_refine_ls_extinction_coef       0.034(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1989
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.256
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.081
_refine_ls_shift/su_mean         0.015
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0546P)²+0.1997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                1880
_reflns_number_total             1989
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052364lsi20060210_044233.cif
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4021622
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
O1 O 0.6342(3) 1.2101(4) -0.01819(17) 0.0492(6) Uani 1 1 d .
C1 C 0.4647(4) 1.0462(4) 0.2294(2) 0.0309(6) Uani 1 1 d .
H1A H 0.4302 0.9070 0.2104 0.037 Uiso 1 1 calc R
H1B H 0.3940 1.0952 0.2867 0.037 Uiso 1 1 calc R
C2 C 0.4283(4) 1.1739(5) 0.1193(3) 0.0403(7) Uani 1 1 d .
H2A H 0.3257 1.1191 0.0593 0.048 Uiso 1 1 calc R
H2B H 0.3970 1.3109 0.1372 0.048 Uiso 1 1 calc R
O2 O 0.7471(3) 0.4757(3) 0.5190(2) 0.0456(6) Uani 1 1 d .
C3 C 0.6095(4) 1.1667(4) 0.0790(2) 0.0368(7) Uani 1 1 d .
O3 O 0.7943(3) 0.5403(3) 0.34056(17) 0.0388(5) Uani 1 1 d .
N4 N 0.7450(3) 1.1071(3) 0.16993(18) 0.0292(5) Uani 1 1 d .
C5 C 0.9379(4) 1.0847(4) 0.1613(2) 0.0315(6) Uani 1 1 d .
H5A H 1.0192 1.1096 0.2386 0.038 Uiso 1 1 calc R
H5B H 0.9679 1.1839 0.1061 0.038 Uiso 1 1 calc R
C6 C 0.9769(4) 0.8796(5) 0.1199(2) 0.0355(7) Uani 1 1 d .
H6A H 1.1012 0.8801 0.1001 0.043 Uiso 1 1 calc R
H6B H 0.8846 0.8500 0.0475 0.043 Uiso 1 1 calc R
C7 C 0.9712(4) 0.7126(5) 0.2084(3) 0.0387(7) Uani 1 1 d .
H7A H 1.0809 0.7250 0.2733 0.046 Uiso 1 1 calc R
H7B H 0.9805 0.5844 0.1697 0.046 Uiso 1 1 calc R
C8 C 0.7878(4) 0.7123(5) 0.2610(2) 0.0387(7) Uani 1 1 d .
H8 H 0.6748 0.7047 0.1966 0.046 Uiso 1 1 calc R
C9A C 0.6758(3) 1.0669(4) 0.2767(2) 0.0269(5) Uani 1 1 d .
H9A H 0.7003 1.1838 0.3296 0.032 Uiso 1 1 calc R
C9 C 0.7729(3) 0.8859(4) 0.3396(2) 0.0254(5) Uani 1 1 d .
H9 H 0.9024 0.9264 0.3770 0.031 Uiso 1 1 calc R
C10 C 0.6822(4) 0.8053(4) 0.4359(2) 0.0279(6) Uani 1 1 d .
H10 H 0.5442 0.8105 0.4078 0.034 Uiso 1 1 calc R
C11 C 0.7425(3) 0.5914(4) 0.4404(2) 0.0332(6) Uani 1 1 d .
C12 C 0.7317(4) 0.9119(5) 0.5514(2) 0.0371(7) Uani 1 1 d .
H12A H 0.6696 0.8479 0.6077 0.056 Uiso 1 1 calc R
H12B H 0.6910 1.0496 0.5409 0.056 Uiso 1 1 calc R
H12C H 0.8666 0.9075 0.5805 0.056 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
C2 C1 C9A 103.7(2)
C3 C2 C1 103.7(2)
O1 C3 N4 124.9(3)
O1 C3 C2 126.7(2)
N4 C3 C2 108.4(2)
C11 O3 C8 111.38(19)
C3 N4 C5 122.9(2)
C3 N4 C9A 113.2(2)
C5 N4 C9A 123.9(2)
N4 C5 C6 111.8(2)
C5 C6 C7 115.1(2)
C6 C7 C8 113.9(2)
O3 C8 C9 102.98(19)
O3 C8 C7 108.9(2)
C9 C8 C7 114.2(2)
N4 C9A C9 110.4(2)
N4 C9A C1 102.30(19)
C9 C9A C1 115.7(2)
C9A C9 C8 114.6(2)
C9A C9 C10 114.3(2)
C8 C9 C10 105.7(2)
C12 C10 C11 114.4(2)
C12 C10 C9 115.5(2)
C11 C10 C9 101.4(2)
O2 C11 O3 121.8(2)
O2 C11 C10 127.7(3)
O3 C11 C10 110.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.227(3)
C1 C2 1.531(4)
C1 C9A 1.542(4)
C2 C3 1.506(4)
O2 C11 1.205(3)
C3 N4 1.360(3)
O3 C11 1.350(3)
O3 C8 1.489(4)
N4 C5 1.452(3)
N4 C9A 1.472(3)
C5 C6 1.520(4)
C6 C7 1.542(4)
C7 C8 1.597(4)
C8 C9 1.513(4)
C9A C9 1.529(3)
C9 C10 1.529(4)
C10 C12 1.511(4)
C10 C11 1.514(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9260563
