#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/34/1513447.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_1513447
loop_
_publ_author_name
'Holmquist, Melireth'
'Blay, Gonzalo'
'Muñoz, M Carmen'
'Pedro, José R'
_publ_section_title
;
 Enantioselective addition of nitromethane to 2-acylpyridine N-oxides.
 Expanding the generation of quaternary stereocenters with the Henry
 reaction.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              1204
_journal_page_last               1207
_journal_paper_doi               10.1021/ol500082d
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H18 N2 O3'
_chemical_formula_weight         286.32
_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                 110.4880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8910(3)
_cell_length_b                   9.4730(2)
_cell_length_c                   9.4720(3)
_cell_measurement_reflns_used    1801
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     747.31(4)
_computing_cell_refinement       'HKL DENZO'
_computing_data_collection       COLLECT
_computing_data_reduction        'HKL DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3351
_diffrn_reflns_theta_full        27.35
_diffrn_reflns_theta_max         27.35
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_correction_T_min  0.9912
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Empirical absorption correction:XABS2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(17)
_refine_ls_extinction_coef       0.090(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3351
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0721P)²+0.1711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1465
_reflns_number_gt                2205
_reflns_number_total             3351
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500082d_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1513447
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
O1 O -0.3584(3) -0.4556(2) -1.2582(3) 0.0723(7) Uani 1 1 d
O2 O 0.0406(3) -0.0964(2) -1.0337(2) 0.0636(6) Uani 1 1 d
O3 O 0.2552(2) -0.2381(2) -0.7743(2) 0.0651(6) Uani 1 1 d
N1 N -0.0746(3) -0.3121(2) -1.0838(3) 0.0518(6) Uani 1 1 d
N2 N -0.5174(3) -0.2754(3) -1.1700(4) 0.0728(8) Uani 1 1 d
C1 C -0.3315(3) -0.3135(3) -1.2992(3) 0.0548(7) Uani 1 1 d
C2 C -0.4013(6) -0.3003(5) -1.4703(4) 0.0817(11) Uani 1 1 d
C3 C -0.4180(3) -0.2137(3) -1.2278(3) 0.0541(7) Uani 1 1 d
C4 C -0.6050(5) -0.1931(5) -1.1143(5) 0.0855(11) Uani 1 1 d
C5 C -0.5984(5) -0.0502(4) -1.1136(4) 0.0767(10) Uani 1 1 d
C6 C -0.4927(5) 0.0136(4) -1.1701(4) 0.0745(9) Uani 1 1 d
C7 C -0.4021(4) -0.0683(3) -1.2286(4) 0.0637(8) Uani 1 1 d
C8 C -0.1511(3) -0.2900(3) -1.2452(3) 0.0551(7) Uani 1 1 d
C9 C 0.0147(3) -0.2152(3) -0.9909(3) 0.0496(6) Uani 1 1 d
C10 C 0.0865(3) -0.2575(3) -0.8265(3) 0.0532(6) Uani 1 1 d
C11 C 0.0093(4) -0.1765(3) -0.7310(3) 0.0560(7) Uani 1 1 d
C12 C -0.1485(5) -0.1336(6) -0.7891(5) 0.0918(13) Uani 1 1 d
C13 C -0.2151(7) -0.0578(7) -0.7015(6) 0.119(2) Uani 1 1 d
C14 C -0.1287(8) -0.0244(5) -0.5575(6) 0.1017(16) Uani 1 1 d
C15 C 0.0270(6) -0.0656(5) -0.4968(5) 0.0902(12) Uani 1 1 d
C16 C 0.0949(5) -0.1418(4) -0.5830(4) 0.0729(9) Uani 1 1 d
H2A H -0.389(5) -0.193(5) -1.499(5) 0.101(14) Uiso 1 1 d
H2B H -0.342(6) -0.361(6) -1.512(5) 0.101(14) Uiso 1 1 d
H2C H -0.522(6) -0.314(4) -1.506(5) 0.092(12) Uiso 1 1 d
H16 H 0.203(5) -0.177(4) -0.545(5) 0.099(14) Uiso 1 1 d
H4 H -0.685(7) -0.244(7) -1.081(5) 0.129(17) Uiso 1 1 d
H5 H -0.668(5) 0.005(5) -1.077(5) 0.094(13) Uiso 1 1 d
H6 H -0.481(5) 0.121(5) -1.168(5) 0.105(14) Uiso 1 1 d
H7 H -0.328(5) -0.026(4) -1.275(4) 0.086(12) Uiso 1 1 d
H8A H -0.129(3) -0.190(3) -1.268(3) 0.043(7) Uiso 1 1 d
H8B H -0.099(4) -0.356(4) -1.306(4) 0.069(9) Uiso 1 1 d
H10 H 0.067(4) -0.367(4) -0.814(3) 0.060(8) Uiso 1 1 d
H12 H -0.206(5) -0.134(5) -0.905(6) 0.119(15) Uiso 1 1 d
H13 H -0.329(7) -0.032(6) -0.749(6) 0.118(16) Uiso 1 1 d
H14 H -0.173(8) 0.033(8) -0.506(7) 0.16(2) Uiso 1 1 d
H15 H 0.099(6) -0.034(5) -0.385(6) 0.112(15) Uiso 1 1 d
H1N H -0.079(4) -0.402(4) -1.044(4) 0.083(11) Uiso 1 1 d
H1O H -0.437(7) -0.435(7) -1.209(7) 0.14(2) Uiso 1 1 d
H3O H 0.277(4) -0.139(5) -0.774(4) 0.082(11) Uiso 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'
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'
H H 0.0000 0.0000 '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
C1 O1 H1O 99(4)
C10 O3 H3O 108(2)
C9 N1 C8 123.3(2)
C9 N1 H1N 117(2)
C8 N1 H1N 119(2)
C3 N2 C4 118.0(3)
O1 C1 C2 108.6(3)
O1 C1 C3 107.6(2)
C2 C1 C3 109.9(3)
O1 C1 C8 107.5(2)
C2 C1 C8 109.6(3)
C3 C1 C8 113.5(2)
C1 C2 H2A 108(2)
C1 C2 H2B 108(3)
H2A C2 H2B 110(4)
C1 C2 H2C 109(2)
H2A C2 H2C 103(3)
H2B C2 H2C 118(4)
N2 C3 C7 121.6(3)
N2 C3 C1 115.1(2)
C7 C3 C1 123.2(3)
N2 C4 C5 123.8(4)
N2 C4 H4 115(3)
C5 C4 H4 121(3)
C4 C5 C6 118.2(4)
C4 C5 H5 121(3)
C6 C5 H5 121(3)
C7 C6 C5 119.2(3)
C7 C6 H6 121(3)
C5 C6 H6 120(3)
C6 C7 C3 119.1(3)
C6 C7 H7 122(2)
C3 C7 H7 119(2)
N1 C8 C1 112.5(2)
N1 C8 H8A 107.9(15)
C1 C8 H8A 109.2(15)
N1 C8 H8B 110.5(17)
C1 C8 H8B 110.1(18)
H8A C8 H8B 106(2)
O2 C9 N1 123.1(2)
O2 C9 C10 120.9(2)
N1 C9 C10 115.9(2)
O3 C10 C9 109.7(2)
O3 C10 C11 111.7(2)
C9 C10 C11 111.3(2)
O3 C10 H10 106.5(17)
C9 C10 H10 110.1(16)
C11 C10 H10 107.4(16)
C12 C11 C16 117.3(3)
C12 C11 C10 121.3(3)
C16 C11 C10 121.4(3)
C11 C12 C13 120.3(4)
C11 C12 H12 118(2)
C13 C12 H12 119(3)
C14 C13 C12 121.3(5)
C14 C13 H13 123(3)
C12 C13 H13 116(3)
C15 C14 C13 119.8(4)
C15 C14 H14 121(4)
C13 C14 H14 119(4)
C14 C15 C16 119.6(4)
C14 C15 H15 121(3)
C16 C15 H15 120(3)
C11 C16 C15 121.8(4)
C11 C16 H16 115(3)
C15 C16 H16 123(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.444(4)
O1 H1O 0.99(7)
O2 C9 1.245(3)
O3 C10 1.418(3)
O3 H3O 0.95(5)
N1 C9 1.326(3)
N1 C8 1.455(4)
N1 H1N 0.94(4)
N2 C3 1.327(4)
N2 C4 1.335(5)
C1 C2 1.523(5)
C1 C3 1.520(4)
C1 C8 1.519(4)
C2 H2A 1.07(5)
C2 H2B 0.96(5)
C2 H2C 1.01(5)
C3 C7 1.385(4)
C4 C5 1.355(6)
C4 H4 0.99(6)
C5 C6 1.373(6)
C5 H5 0.96(5)
C6 C7 1.368(5)
C6 H6 1.02(5)
C7 H7 1.00(4)
C8 H8A 1.00(3)
C8 H8B 1.06(4)
C9 C10 1.516(4)
C10 C11 1.521(4)
C10 H10 1.06(3)
C11 C12 1.377(5)
C11 C16 1.381(4)
C12 C13 1.378(6)
C12 H12 1.04(5)
C13 C14 1.348(8)
C13 H13 0.98(6)
C14 C15 1.358(7)
C14 H14 0.91(7)
C15 C16 1.377(6)
C15 H15 1.07(5)
C16 H16 0.96(4)
