#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/12/7151204.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_7151204
loop_
_publ_author_name
'Mitchell, Claire E. T.'
'Brenner, Stacey E.'
'García-Fortanet, Jorge'
'Ley, Steven V.'
_publ_section_title
;
 An efficient, asymmetric organocatalyst-mediated conjugate addition of
 nitroalkanes to unsaturated cyclic and acyclic ketones.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2039
_journal_page_last               2049
_journal_paper_doi               10.1039/b601877g
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration 'not determined'
_chemical_formula_moiety         'C12 H15 N O3'
_chemical_formula_sum            'C12 H15 N O3'
_chemical_formula_weight         221.25
_chemical_name_systematic
;
?
;
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6440(1)
_cell_length_b                   8.4770(2)
_cell_length_c                   25.1210(5)
_cell_measurement_reflns_used    13723
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1201.89(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9256
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.70
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0312
_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)+(0.0322P)²+0.2195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0770
_reflns_number_gt                1518
_reflns_number_total             1600
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b601877g.txt
_cod_data_source_block           sl0519
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7151204
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7733(2) 0.57859(16) 0.18424(5) 0.0311(3) Uani 1 1 d . . .
O1 O 0.1886(2) 0.13733(14) 0.13838(5) 0.0423(3) Uani 1 1 d . . .
O2 O 0.9019(2) 0.66210(14) 0.15753(5) 0.0464(3) Uani 1 1 d . . .
O3 O 0.6150(2) 0.63007(15) 0.21257(5) 0.0482(3) Uani 1 1 d . . .
C1 C 0.4027(4) -0.09565(19) 0.11872(7) 0.0433(4) Uani 1 1 d . . .
H1A H 0.2467 -0.1465 0.1184 0.065 Uiso 1 1 calc R . .
H1B H 0.5088 -0.1539 0.1425 0.065 Uiso 1 1 calc R . .
H1C H 0.4686 -0.0955 0.0826 0.065 Uiso 1 1 calc R . .
C2 C 0.3780(3) 0.07069(18) 0.13802(6) 0.0298(3) Uani 1 1 d . . .
C3 C 0.6011(3) 0.14863(18) 0.15813(6) 0.0295(3) Uani 1 1 d . . .
H3A H 0.7366 0.1135 0.1361 0.035 Uiso 1 1 calc R . .
H3B H 0.6308 0.1138 0.1952 0.035 Uiso 1 1 calc R . .
C4 C 0.5880(3) 0.32979(17) 0.15685(5) 0.0258(3) Uani 1 1 d . . .
H4 H 0.4468 0.3633 0.1781 0.031 Uiso 1 1 calc R . .
C5 C 0.8096(3) 0.40154(17) 0.18272(6) 0.0287(3) Uani 1 1 d . . .
H5 H 0.9501 0.3776 0.1598 0.034 Uiso 1 1 calc R . .
C6 C 0.8610(3) 0.3467(2) 0.23908(6) 0.0449(4) Uani 1 1 d . . .
H6A H 0.9831 0.4142 0.2549 0.067 Uiso 1 1 calc R . .
H6B H 0.9172 0.2373 0.2383 0.067 Uiso 1 1 calc R . .
H6C H 0.7160 0.3530 0.2604 0.067 Uiso 1 1 calc R . .
C7 C 0.5573(2) 0.39103(16) 0.10022(5) 0.0254(3) Uani 1 1 d . . .
C8 C 0.7161(3) 0.3473(2) 0.06035(6) 0.0341(3) Uani 1 1 d . . .
H8 H 0.8450 0.2795 0.0686 0.041 Uiso 1 1 calc R . .
C9 C 0.6875(3) 0.4019(2) 0.00879(6) 0.0432(4) Uani 1 1 d . . .
H9 H 0.7959 0.3704 -0.0181 0.052 Uiso 1 1 calc R . .
C10 C 0.5029(3) 0.5014(2) -0.00368(6) 0.0439(4) Uani 1 1 d . . .
H10 H 0.4839 0.5383 -0.0391 0.053 Uiso 1 1 calc R . .
C11 C 0.3453(3) 0.5476(2) 0.03546(7) 0.0395(4) Uani 1 1 d . . .
H11 H 0.2185 0.6170 0.0270 0.047 Uiso 1 1 calc R . .
C12 C 0.3729(3) 0.49209(18) 0.08740(6) 0.0315(3) Uani 1 1 d . . .
H12 H 0.2643 0.5239 0.1142 0.038 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N1 O3 123.34(14) . . ?
O2 N1 C5 118.82(13) . . ?
O3 N1 C5 117.84(13) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 121.64(15) . . ?
O1 C2 C3 122.05(13) . . ?
C1 C2 C3 116.29(14) . . ?
C2 C3 C4 112.94(13) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C7 C4 C5 110.65(12) . . ?
C7 C4 C3 111.43(12) . . ?
C5 C4 C3 110.33(12) . . ?
C7 C4 H4 108.1 . . ?
C5 C4 H4 108.1 . . ?
C3 C4 H4 108.1 . . ?
N1 C5 C6 107.80(12) . . ?
N1 C5 C4 107.05(12) . . ?
C6 C5 C4 115.41(13) . . ?
N1 C5 H5 108.8 . . ?
C6 C5 H5 108.8 . . ?
C4 C5 H5 108.8 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 118.70(13) . . ?
C12 C7 C4 120.85(12) . . ?
C8 C7 C4 120.45(13) . . ?
C9 C8 C7 120.53(15) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 120.38(16) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.93(15) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 119.82(16) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 120.64(14) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O2 1.2158(17) . ?
N1 O3 1.2227(17) . ?
N1 C5 1.5152(19) . ?
O1 C2 1.2092(19) . ?
C1 C2 1.498(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.509(2) . ?
C3 C4 1.538(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C7 1.5242(19) . ?
C4 C5 1.535(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.518(2) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C12 1.386(2) . ?
C7 C8 1.394(2) . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -23.5(2) . . . . ?
C1 C2 C3 C4 157.95(13) . . . . ?
C2 C3 C4 C7 -62.14(16) . . . . ?
C2 C3 C4 C5 174.53(11) . . . . ?
O2 N1 C5 C6 121.16(15) . . . . ?
O3 N1 C5 C6 -58.78(18) . . . . ?
O2 N1 C5 C4 -114.10(15) . . . . ?
O3 N1 C5 C4 65.96(16) . . . . ?
C7 C4 C5 N1 61.09(14) . . . . ?
C3 C4 C5 N1 -175.13(12) . . . . ?
C7 C4 C5 C6 -178.93(13) . . . . ?
C3 C4 C5 C6 -55.15(17) . . . . ?
C5 C4 C7 C12 -110.74(15) . . . . ?
C3 C4 C7 C12 126.12(14) . . . . ?
C5 C4 C7 C8 68.70(17) . . . . ?
C3 C4 C7 C8 -54.44(19) . . . . ?
C12 C7 C8 C9 -1.0(2) . . . . ?
C4 C7 C8 C9 179.51(15) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C8 C7 C12 C11 0.7(2) . . . . ?
C4 C7 C12 C11 -179.88(14) . . . . ?
C10 C11 C12 C7 0.1(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21188833
