#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/29/1502933.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_1502933
loop_
_publ_author_name
'Flores, Melissa A.'
'Bode, Jeffrey W.'
_publ_section_title
;
 Chemoselective protection of alpha-ketoacids by direct annulations with
 oximes.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              1924
_journal_page_last               1927
_journal_paper_doi               10.1021/ol100467t
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C15 H17 N O3'
_chemical_formula_weight         259.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.410(2)
_cell_angle_beta                 98.712(2)
_cell_angle_gamma                88.915(2)
_cell_formula_units_Z            2
_cell_length_a                   5.3913(8)
_cell_length_b                   10.1972(14)
_cell_length_c                   12.9979(19)
_cell_measurement_temperature    293(2)
_cell_volume                     657.07(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4975
_diffrn_reflns_theta_full        25.66
_diffrn_reflns_theta_max         25.66
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.461
_exptl_absorpt_correction_T_min  0.321
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'psi scan'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         2368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0485
_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)+(0.0950P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                1585
_reflns_number_total             2368
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100467t_si_003.cif
_cod_data_source_block           mel1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502933
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
C1 C 0.2035(4) 0.3247(2) 0.11856(18) 0.0630(5) Uani 1 1 d
C2 C 0.1356(5) 0.2001(2) 0.02809(19) 0.0765(7) Uani 1 1 d
C3 C -0.0899(5) 0.1849(3) -0.04017(19) 0.0763(7) Uani 1 1 d
C4 C -0.2506(5) 0.2931(3) -0.01932(19) 0.0790(7) Uani 1 1 d
C5 C -0.1886(4) 0.4193(3) 0.07022(18) 0.0693(6) Uani 1 1 d
C6 C 0.0412(3) 0.43676(19) 0.14121(14) 0.0516(5) Uani 1 1 d
C7 C 0.1078(3) 0.57050(19) 0.23462(14) 0.0509(5) Uani 1 1 d
C8 C -0.0315(4) 0.7006(2) 0.26098(16) 0.0569(5) Uani 1 1 d
C9 C 0.3210(4) 0.7454(2) 0.39184(16) 0.0554(5) Uani 1 1 d
C10 C 0.3164(3) 0.75448(18) 0.51051(15) 0.0497(5) Uani 1 1 d
C11 C 0.0651(4) 0.7022(2) 0.52541(16) 0.0566(5) Uani 1 1 d
C12 C 0.0647(4) 0.7119(2) 0.64489(17) 0.0623(5) Uani 1 1 d
C13 C 0.1343(4) 0.8609(2) 0.72789(19) 0.0689(6) Uani 1 1 d
C14 C 0.3839(4) 0.9135(3) 0.71387(17) 0.0690(6) Uani 1 1 d
C15 C 0.3835(4) 0.9039(2) 0.59414(17) 0.0585(5) Uani 1 1 d
H1 H 0.360(4) 0.330(2) 0.1619(16) 0.059(5) Uiso 1 1 d
H2 H 0.249(5) 0.129(3) 0.017(2) 0.097(8) Uiso 1 1 d
H3 H -0.140(4) 0.096(3) -0.103(2) 0.089(7) Uiso 1 1 d
H4 H -0.414(5) 0.285(2) -0.067(2) 0.095(8) Uiso 1 1 d
H5 H -0.296(4) 0.494(2) 0.0890(18) 0.077(6) Uiso 1 1 d
H9 H 0.466(4) 0.792(2) 0.3858(17) 0.080(7) Uiso 1 1 d
H10 H 0.442(3) 0.6951(18) 0.5240(14) 0.049(5) Uiso 1 1 d
H111 H -0.073(3) 0.7593(18) 0.5032(14) 0.055(5) Uiso 1 1 d
H112 H 0.028(4) 0.602(2) 0.4713(18) 0.078(6) Uiso 1 1 d
H121 H -0.101(4) 0.682(2) 0.6554(16) 0.073(6) Uiso 1 1 d
H122 H 0.197(4) 0.651(2) 0.6615(15) 0.061(5) Uiso 1 1 d
H131 H -0.009(4) 0.926(2) 0.7133(17) 0.078(6) Uiso 1 1 d
H132 H 0.135(4) 0.861(2) 0.8035(19) 0.078(6) Uiso 1 1 d
H141 H 0.424(4) 1.012(2) 0.7672(19) 0.074(6) Uiso 1 1 d
H142 H 0.528(4) 0.857(2) 0.7356(16) 0.063(5) Uiso 1 1 d
H151 H 0.264(4) 0.969(2) 0.5753(15) 0.055(5) Uiso 1 1 d
H152 H 0.549(4) 0.935(2) 0.5862(16) 0.066(5) Uiso 1 1 d
N N 0.3097(3) 0.59722(16) 0.31104(13) 0.0543(4) Uani 1 1 d
O1 O -0.2316(3) 0.72470(15) 0.21869(12) 0.0763(5) Uani 1 1 d
O2 O 0.1070(3) 0.80422(13) 0.34924(11) 0.0630(4) Uani 1 1 d
O3 O 0.4835(3) 0.51874(15) 0.32622(12) 0.0753(5) 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 0.0016 '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 C6 120.2(2)
C2 C1 H1 117.6(12)
C6 C1 H1 122.2(12)
C3 C2 C1 120.8(2)
C3 C2 H2 122.2(16)
C1 C2 H2 117.0(16)
C4 C3 C2 119.8(2)
C4 C3 H3 119.4(14)
C2 C3 H3 120.8(14)
C3 C4 C5 121.0(2)
C3 C4 H4 121.8(14)
C5 C4 H4 117.2(15)
C4 C5 C6 120.1(2)
C4 C5 H5 123.5(13)
C6 C5 H5 116.4(13)
C1 C6 C5 118.12(19)
C1 C6 C7 121.85(18)
C5 C6 C7 120.02(18)
N C7 C6 125.89(16)
N C7 C8 106.59(16)
C6 C7 C8 127.51(17)
O1 C8 O2 120.61(17)
O1 C8 C7 130.74(19)
O2 C8 C7 108.65(17)
O2 C9 N 103.29(14)
O2 C9 C10 112.47(15)
N C9 C10 112.47(16)
O2 C9 H9 107.4(13)
N C9 H9 108.5(13)
C10 C9 H9 112.2(12)
C9 C10 C15 111.15(16)
C9 C10 C11 112.63(15)
C15 C10 C11 110.52(15)
C9 C10 H10 105.3(10)
C15 C10 H10 108.3(10)
C11 C10 H10 108.7(10)
C12 C11 C10 111.76(16)
C12 C11 H111 110.5(10)
C10 C11 H111 108.8(10)
C12 C11 H112 110.5(12)
C10 C11 H112 109.0(12)
H111 C11 H112 106.0(15)
C11 C12 C13 111.21(18)
C11 C12 H121 111.8(11)
C13 C12 H121 109.2(11)
C11 C12 H122 107.6(11)
C13 C12 H122 106.8(11)
H121 C12 H122 110.2(17)
C14 C13 C12 111.48(18)
C14 C13 H131 109.9(12)
C12 C13 H131 107.4(11)
C14 C13 H132 112.4(12)
C12 C13 H132 108.2(13)
H131 C13 H132 107.3(17)
C13 C14 C15 111.33(18)
C13 C14 H141 110.5(12)
C15 C14 H141 110.5(12)
C13 C14 H142 110.6(11)
C15 C14 H142 109.5(11)
H141 C14 H142 104.2(16)
C14 C15 C10 111.52(18)
C14 C15 H151 110.9(11)
C10 C15 H151 109.1(11)
C14 C15 H152 110.0(11)
C10 C15 H152 110.1(11)
H151 C15 H152 105.0(16)
O3 N C7 130.78(16)
O3 N C9 117.68(15)
C7 N C9 111.52(15)
C8 O2 C9 109.55(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.388(3)
C1 C6 1.398(3)
C1 H1 0.93(2)
C2 C3 1.367(3)
C2 H2 0.93(3)
C3 C4 1.363(4)
C3 H3 0.98(3)
C4 C5 1.388(3)
C4 H4 0.98(3)
C5 C6 1.400(3)
C5 H5 0.93(2)
C6 C7 1.463(3)
C7 N 1.316(2)
C7 C8 1.466(3)
C8 O1 1.198(2)
C8 O2 1.370(2)
C9 O2 1.422(2)
C9 N 1.488(2)
C9 C10 1.515(3)
C9 H9 0.95(2)
C10 C15 1.525(2)
C10 C11 1.530(3)
C10 H10 0.939(19)
C11 C12 1.520(3)
C11 H111 1.007(19)
C11 H112 1.01(2)
C12 C13 1.522(3)
C12 H121 0.99(2)
C12 H122 0.99(2)
C13 C14 1.518(3)
C13 H131 1.05(2)
C13 H132 0.98(2)
C14 C15 1.523(3)
C14 H141 0.99(2)
C14 H142 1.03(2)
C15 H151 0.98(2)
C15 H152 0.99(2)
N O3 1.2603(19)
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
C6 C1 C2 C3 0.1(3)
C1 C2 C3 C4 -0.1(4)
C2 C3 C4 C5 0.3(4)
C3 C4 C5 C6 -0.4(4)
C2 C1 C6 C5 -0.2(3)
C2 C1 C6 C7 -178.96(18)
C4 C5 C6 C1 0.4(3)
C4 C5 C6 C7 179.15(18)
C1 C6 C7 N -5.7(3)
C5 C6 C7 N 175.50(17)
C1 C6 C7 C8 173.22(17)
C5 C6 C7 C8 -5.5(3)
N C7 C8 O1 -175.6(2)
C6 C7 C8 O1 5.3(3)
N C7 C8 O2 4.5(2)
C6 C7 C8 O2 -174.60(15)
O2 C9 C10 C15 -75.9(2)
N C9 C10 C15 168.00(15)
O2 C9 C10 C11 48.8(2)
N C9 C10 C11 -67.4(2)
C9 C10 C11 C12 179.84(16)
C15 C10 C11 C12 -55.2(2)
C10 C11 C12 C13 55.2(2)
C11 C12 C13 C14 -54.9(3)
C12 C13 C14 C15 55.2(3)
C13 C14 C15 C10 -55.6(3)
C9 C10 C15 C14 -178.97(17)
C11 C10 C15 C14 55.2(2)
C6 C7 N O3 -3.1(3)
C8 C7 N O3 177.80(18)
C6 C7 N C9 178.44(16)
C8 C7 N C9 -0.70(19)
O2 C9 N O3 178.16(15)
C10 C9 N O3 -60.3(2)
O2 C9 N C7 -3.1(2)
C10 C9 N C7 118.39(17)
O1 C8 O2 C9 173.48(18)
C7 C8 O2 C9 -6.6(2)
N C9 O2 C8 5.92(19)
C10 C9 O2 C8 -115.59(17)
