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#$Date: 2016-03-21 17:44:03 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178791 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/45/4104550.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_4104550
loop_
_publ_author_name
'Marino J. E. Resendiz'
'Farnosh Family'
'Kerrian Fuller'
'Luis M. Campos'
'Saeed I. Khan'
'Natalia V. Lebedeva'
'Malcolm D. E. Forbes'
'Miguel A. Garcia-Garibay'
_publ_section_title
;
 Radical Reactions with Double Memory of Chirality (2MOC) for the
 Enantiospecific Synthesis of Adjacent Stereogenic Quaternary Centers in
 Solution: Cleavage and Bonding Faster than Radical Rotation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8425
_journal_page_last               8433
_journal_paper_doi               10.1021/ja900781n
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C23 H24 N2 O3'
_chemical_formula_sum            'C23 H24 N2 O3'
_chemical_formula_weight         376.44
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_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                   6.8604(13)
_cell_length_b                   6.8604(13)
_cell_length_c                   40.242(11)
_cell_measurement_reflns_used    3777
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      23.96
_cell_measurement_theta_min      3.90
_cell_volume                     1894.0(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            16517
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         3.90
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs (Bruker)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.289
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.289
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0591
_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)+(0.0277P)²+1.8880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                1398
_reflns_number_total             1497
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja900781n_si_003.cif
_cod_data_source_block           p41212
_cod_database_code               4104550
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -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
O1 O 0.5625(3) 0.7950(3) 0.03188(5) 0.0261(5) Uani 1 1 d .
O2 O 1.0723(3) 1.0723(3) 0.0000 0.0291(7) Uani 1 2 d S
N1 N 0.7546(4) 0.5347(4) 0.04565(6) 0.0247(6) Uani 1 1 d .
C1 C 1.1621(5) 0.9938(5) 0.06987(7) 0.0236(6) Uani 1 1 d .
H1 H 1.2634 0.9627 0.0547 0.028 Uiso 1 1 calc R
C2 C 1.2044(5) 1.0976(5) 0.09889(8) 0.0293(7) Uani 1 1 d .
H2 H 1.3346 1.1378 0.1031 0.035 Uiso 1 1 calc R
C3 C 1.0585(6) 1.1426(5) 0.12160(8) 0.0306(8) Uani 1 1 d .
H3 H 1.0885 1.2121 0.1414 0.037 Uiso 1 1 calc R
C4 C 0.8681(5) 1.0848(5) 0.11503(8) 0.0288(8) Uani 1 1 d .
H4 H 0.7674 1.1148 0.1304 0.035 Uiso 1 1 calc R
C5 C 0.8241(5) 0.9828(5) 0.08598(7) 0.0231(7) Uani 1 1 d .
H5 H 0.6933 0.9451 0.0817 0.028 Uiso 1 1 calc R
C6 C 0.9701(5) 0.9357(4) 0.06318(7) 0.0210(6) Uani 1 1 d .
C7 C 0.9236(4) 0.8181(4) 0.03147(7) 0.0190(6) Uani 1 1 d .
C8 C 0.9480(5) 0.9480(5) 0.0000 0.0214(8) Uani 1 2 d S
C9 C 1.0628(5) 0.6397(4) 0.02792(7) 0.0220(6) Uani 1 1 d .
H9A H 1.0772 0.6009 0.0044 0.026 Uiso 1 1 calc R
H9B H 1.1932 0.6690 0.0372 0.026 Uiso 1 1 calc R
C10 C 0.9600(5) 0.4798(5) 0.04810(8) 0.0270(7) Uani 1 1 d .
H10A H 0.9833 0.3494 0.0383 0.032 Uiso 1 1 calc R
H10B H 1.0045 0.4798 0.0715 0.032 Uiso 1 1 calc R
C11 C 0.5955(5) 0.3969(5) 0.05159(9) 0.0320(8) Uani 1 1 d .
H11A H 0.5962 0.3571 0.0750 0.048 Uiso 1 1 calc R
H11B H 0.6130 0.2820 0.0374 0.048 Uiso 1 1 calc R
H11C H 0.4708 0.4593 0.0463 0.048 Uiso 1 1 calc R
C12 C 0.7238(4) 0.7190(5) 0.03554(7) 0.0205(6) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C12 N1 C10 114.5(3) . .
C12 N1 C11 122.7(3) . .
C10 N1 C11 122.8(3) . .
C2 C1 C6 120.0(3) . .
C2 C1 H1 120.0 . .
C6 C1 H1 120.0 . .
C3 C2 C1 120.8(3) . .
C3 C2 H2 119.6 . .
C1 C2 H2 119.6 . .
C2 C3 C4 119.2(3) . .
C2 C3 H3 120.4 . .
C4 C3 H3 120.4 . .
C3 C4 C5 120.4(3) . .
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 . .
C4 C5 C6 120.8(3) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C5 C6 C1 118.8(3) . .
C5 C6 C7 121.1(3) . .
C1 C6 C7 120.1(3) . .
C12 C7 C6 109.1(2) . .
C12 C7 C8 115.8(3) . .
C6 C7 C8 110.6(2) . .
C12 C7 C9 102.1(2) . .
C6 C7 C9 111.1(2) . .
C8 C7 C9 108.0(2) . .
O2 C8 C7 118.72(18) . 7
O2 C8 C7 118.72(18) . .
C7 C8 C7 122.6(4) 7 .
C10 C9 C7 103.3(2) . .
C10 C9 H9A 111.1 . .
C7 C9 H9A 111.1 . .
C10 C9 H9B 111.1 . .
C7 C9 H9B 111.1 . .
H9A C9 H9B 109.1 . .
N1 C10 C9 102.9(2) . .
N1 C10 H10A 111.2 . .
C9 C10 H10A 111.2 . .
N1 C10 H10B 111.2 . .
C9 C10 H10B 111.2 . .
H10A C10 H10B 109.1 . .
N1 C11 H11A 109.5 . .
N1 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
N1 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
O1 C12 N1 125.1(3) . .
O1 C12 C7 126.9(3) . .
N1 C12 C7 107.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C12 1.232(4) .
O2 C8 1.206(5) .
N1 C12 1.345(4) .
N1 C10 1.462(4) .
N1 C11 1.464(4) .
C1 C2 1.398(4) .
C1 C6 1.402(4) .
C1 H1 0.9500 .
C2 C3 1.391(5) .
C2 H2 0.9500 .
C3 C4 1.391(5) .
C3 H3 0.9500 .
C4 C5 1.395(4) .
C4 H4 0.9500 .
C5 C6 1.396(4) .
C5 H5 0.9500 .
C6 C7 1.543(4) .
C7 C12 1.539(4) .
C7 C8 1.558(4) .
C7 C9 1.559(4) .
C8 C7 1.558(4) 7
C9 C10 1.536(4) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
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_4
C6 C1 C2 C3 0.7(5) .
C1 C2 C3 C4 -0.6(5) .
C2 C3 C4 C5 0.0(5) .
C3 C4 C5 C6 0.6(5) .
C4 C5 C6 C1 -0.4(4) .
C4 C5 C6 C7 178.3(3) .
C2 C1 C6 C5 -0.2(5) .
C2 C1 C6 C7 -179.0(3) .
C5 C6 C7 C12 -16.6(4) .
C1 C6 C7 C12 162.1(3) .
C5 C6 C7 C8 111.8(3) .
C1 C6 C7 C8 -69.5(3) .
C5 C6 C7 C9 -128.4(3) .
C1 C6 C7 C9 50.4(4) .
C12 C7 C8 O2 158.20(17) .
C6 C7 C8 O2 33.5(2) .
C9 C7 C8 O2 -88.2(2) .
C12 C7 C8 C7 -21.80(17) 7
C6 C7 C8 C7 -146.5(2) 7
C9 C7 C8 C7 91.8(2) 7
C12 C7 C9 C10 -29.4(3) .
C6 C7 C9 C10 86.7(3) .
C8 C7 C9 C10 -151.9(3) .
C12 N1 C10 C9 -16.4(3) .
C11 N1 C10 C9 159.8(3) .
C7 C9 C10 N1 27.9(3) .
C10 N1 C12 O1 -179.8(3) .
C11 N1 C12 O1 4.0(5) .
C10 N1 C12 C7 -3.0(3) .
C11 N1 C12 C7 -179.1(3) .
C6 C7 C12 O1 79.9(4) .
C8 C7 C12 O1 -45.6(4) .
C9 C7 C12 O1 -162.6(3) .
C6 C7 C12 N1 -96.9(3) .
C8 C7 C12 N1 137.6(2) .
C9 C7 C12 N1 20.6(3) .
