#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:05:15 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178933 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/62/4116229.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_4116229
loop_
_publ_author_name
'P. Andrew Evans'
'Thara Manangan'
'Arnold L. Rheingold'
_publ_contact_author
; 
     Dr. P. A. Evans 
     Department of Chemistry and Biochemistry 
     University of Delaware, Newark, DE 19716 
     USA 
;
_publ_contact_author_email       paevans@udel.edu
_publ_contact_author_fax         '+302 831 6335'
_publ_contact_author_phone       '+302 831 6770'
_publ_section_title
;
 Stereoselective Construction of trans-Disubstituted Azabicycles Using
 Oxauracil as a Novel Free Radical Acceptor
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11009
_journal_page_last               11010
_journal_paper_doi               10.1021/ja0020308
_journal_volume                  122
_journal_year                    2000
_chemical_formula_sum            'C22 H26 N2 O2'
_chemical_formula_weight         350.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 98.416(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5766(1)
_cell_length_b                   9.7748(2)
_cell_length_c                   19.1768(4)
_cell_measurement_temperature    213(2)
_cell_volume                     1961.23(6)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7897
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.076
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.60
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.071
_refine_ls_goodness_of_fit_obs   1.143
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_restrained_S_obs      1.143
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_obs          0.0505
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1012P)²+0.0307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1627
_refine_ls_wR_factor_obs         0.1526
_reflns_number_observed          3101
_reflns_number_total             3967
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja0020308_3.cif
_cod_data_source_block           paev18
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1012P)^2^+0.0307P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1012P)^2^+0.0307P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4116229
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.46090(12) 0.89016(11) 0.07676(6) 0.0445(3) Uani 1 d .
O2 O 0.63842(11) 0.54714(10) 0.03301(7) 0.0426(3) Uani 1 d .
N1 N 0.72581(11) 0.75934(12) 0.04647(6) 0.0315(3) Uani 1 d .
N2 N 0.34514(12) 0.70075(12) 0.04192(7) 0.0355(3) Uani 1 d .
H2A H 0.32975(12) 0.63736(12) 0.00996(7) 0.043 Uiso 1 calc R
C1 C 0.8346(2) 0.9790(2) 0.08546(10) 0.0462(4) Uani 1 d .
H1A H 0.7898(2) 0.9799(2) 0.12613(10) 0.069 Uiso 1 calc R
H1B H 0.7856(2) 1.0298(2) 0.04724(10) 0.069 Uiso 1 calc R
H1C H 0.9180(2) 1.0210(2) 0.09779(10) 0.069 Uiso 1 calc R
C2 C 0.85096(14) 0.8313(2) 0.06214(9) 0.0370(4) Uani 1 d .
H2B H 0.90209(14) 0.7828(2) 0.10200(9) 0.044 Uiso 1 calc R
C3 C 0.9204(2) 0.8154(2) -0.00179(10) 0.0432(4) Uani 1 d .
H3A H 0.9437(2) 0.7191(2) -0.00615(10) 0.052 Uiso 1 calc R
H3B H 0.9997(2) 0.8687(2) 0.00616(10) 0.052 Uiso 1 calc R
C4 C 0.8415(2) 0.8619(2) -0.07114(10) 0.0457(4) Uani 1 d .
H4A H 0.8862(2) 0.8369(2) -0.11057(10) 0.055 Uiso 1 calc R
H4B H 0.8325(2) 0.9617(2) -0.07091(10) 0.055 Uiso 1 calc R
C5 C 0.7084(2) 0.7958(2) -0.08155(9) 0.0416(4) Uani 1 d .
H5A H 0.6558(2) 0.8364(2) -0.12267(9) 0.050 Uiso 1 calc R
H5B H 0.7162(2) 0.6976(2) -0.09021(9) 0.050 Uiso 1 calc R
C6 C 0.64480(14) 0.81780(14) -0.01648(8) 0.0323(4) Uani 1 d .
H6A H 0.64434(14) 0.91795(14) -0.00883(8) 0.039 Uiso 1 calc R
C7 C 0.50433(14) 0.77353(15) -0.02764(8) 0.0323(4) Uani 1 d .
H7A H 0.45845(14) 0.82582(15) -0.06704(8) 0.039 Uiso 1 calc R
H7B H 0.49958(14) 0.67665(15) -0.04092(8) 0.039 Uiso 1 calc R
C8 C 0.43795(14) 0.79308(13) 0.03588(8) 0.0318(4) Uani 1 d .
C9 C 0.2704(2) 0.7028(2) 0.09921(10) 0.0430(4) Uani 1 d .
H9A H 0.1806(2) 0.6862(2) 0.08012(10) 0.052 Uiso 1 calc R
H9B H 0.2760(2) 0.7942(2) 0.12046(10) 0.052 Uiso 1 calc R
C10 C 0.3121(2) 0.5983(2) 0.15612(9) 0.0378(4) Uani 1 d .
C11 C 0.4401(2) 0.5653(2) 0.17494(11) 0.0500(5) Uani 1 d .
H11A H 0.5020(2) 0.6086(2) 0.15208(11) 0.060 Uiso 1 calc R
C12 C 0.4779(2) 0.4695(2) 0.22689(12) 0.0598(6) Uani 1 d .
H12A H 0.5650(2) 0.4486(2) 0.23927(12) 0.072 Uiso 1 calc R
C13 C 0.3885(2) 0.4047(2) 0.26048(12) 0.0621(6) Uani 1 d .
H13A H 0.4142(2) 0.3388(2) 0.29539(12) 0.074 Uiso 1 calc R
C14 C 0.2610(2) 0.4370(2) 0.24264(13) 0.0649(6) Uani 1 d .
H14A H 0.1995(2) 0.3939(2) 0.26580(13) 0.078 Uiso 1 calc R
C15 C 0.2236(2) 0.5330(2) 0.19063(11) 0.0516(5) Uani 1 d .
H15A H 0.1364(2) 0.5540(2) 0.17862(11) 0.062 Uiso 1 calc R
C16 C 0.71380(13) 0.62759(13) 0.06644(8) 0.0303(3) Uani 1 d .
C17 C 0.78898(14) 0.57920(15) 0.13483(9) 0.0340(4) Uani 1 d .
C18 C 0.8009(2) 0.6579(2) 0.19559(9) 0.0430(4) Uani 1 d .
H18A H 0.7687(2) 0.7476(2) 0.19385(9) 0.052 Uiso 1 calc R
C19 C 0.8607(2) 0.6040(2) 0.25916(10) 0.0572(5) Uani 1 d .
H19A H 0.8681(2) 0.6573(2) 0.30036(10) 0.069 Uiso 1 calc R
C20 C 0.9091(2) 0.4724(2) 0.26196(12) 0.0626(6) Uani 1 d .
H20A H 0.9502(2) 0.4367(2) 0.30487(12) 0.075 Uiso 1 calc R
C21 C 0.8971(2) 0.3939(2) 0.20183(12) 0.0599(6) Uani 1 d .
H21A H 0.9302(2) 0.3045(2) 0.20378(12) 0.072 Uiso 1 calc R
C22 C 0.8363(2) 0.4457(2) 0.13840(11) 0.0462(5) Uani 1 d .
H22A H 0.8270(2) 0.3908(2) 0.09771(11) 0.055 Uiso 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
C16 N1 C6 121.84(11)
C16 N1 C2 120.59(11)
C6 N1 C2 111.80(11)
C8 N2 C9 122.77(13)
N1 C2 C3 107.92(12)
N1 C2 C1 111.69(14)
C3 C2 C1 114.79(13)
C2 C3 C4 113.68(14)
C3 C4 C5 111.16(14)
C6 C5 C4 110.01(13)
N1 C6 C5 109.92(13)
N1 C6 C7 115.86(12)
C5 C6 C7 112.52(12)
C8 C7 C6 114.14(12)
O1 C8 N2 122.5(2)
O1 C8 C7 122.76(14)
N2 C8 C7 114.56(12)
N2 C9 C10 113.87(13)
C15 C10 C11 118.2(2)
C15 C10 C9 120.79(15)
C11 C10 C9 121.0(2)
C12 C11 C10 120.9(2)
C13 C12 C11 120.3(2)
C12 C13 C14 119.5(2)
C13 C14 C15 120.0(2)
C10 C15 C14 121.1(2)
O2 C16 N1 122.71(13)
O2 C16 C17 118.15(12)
N1 C16 C17 119.01(12)
C18 C17 C22 119.3(2)
C18 C17 C16 121.94(14)
C22 C17 C16 118.43(15)
C17 C18 C19 120.0(2)
C20 C19 C18 120.3(2)
C21 C20 C19 119.9(2)
C20 C21 C22 120.4(2)
C21 C22 C17 120.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.232(2)
O2 C16 1.231(2)
N1 C16 1.355(2)
N1 C6 1.488(2)
N1 C2 1.490(2)
N2 C8 1.351(2)
N2 C9 1.445(2)
C1 C2 1.529(2)
C2 C3 1.527(3)
C3 C4 1.532(2)
C4 C5 1.534(2)
C5 C6 1.517(2)
C6 C7 1.532(2)
C7 C8 1.505(2)
C9 C10 1.513(2)
C10 C15 1.379(3)
C10 C11 1.387(2)
C11 C12 1.383(3)
C12 C13 1.373(3)
C13 C14 1.378(3)
C14 C15 1.384(3)
C16 C17 1.507(2)
C17 C18 1.386(2)
C17 C22 1.396(2)
C18 C19 1.392(2)
C19 C20 1.383(3)
C20 C21 1.375(3)
C21 C22 1.386(3)
