#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:36:53 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178907 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/36/4113641.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_4113641
loop_
_publ_author_name
'Andrew G. Leach'
'Renxiao Wang'
'G. Erich Wohlhieter'
'Saeed I. Khan'
'Michael E. Jung'
'K. N. Houk'
_publ_section_title
;
 Theoretical Elucidation of Kinetic and Thermodynamic Control of Radical
 Addition Regioselectivity
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4271
_journal_page_last               4278
_journal_paper_doi               10.1021/ja029342q
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C21 H21 N4 O4'
_chemical_formula_weight         393.42
_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                93.988(7)
_cell_angle_beta                 104.824(6)
_cell_angle_gamma                93.071(6)
_cell_formula_units_Z            2
_cell_length_a                   7.017(2)
_cell_length_b                   10.987(4)
_cell_length_c                   12.948(4)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.58
_cell_volume                     960.0(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.909
_diffrn_measured_fraction_theta_max 0.909
_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  0.0404
_diffrn_reflns_av_sigmaI/netI    0.1896
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5963
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs(Bruker)
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       plate
_exptl_crystal_F_000             414
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.810
_refine_ls_R_factor_all          0.1839
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0357P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                1503
_reflns_number_total             4337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja029342qsi20030211_052750.cif
_cod_data_source_block           Me202
_cod_database_code               4113641
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0428(3) 0.21438(19) 0.42989(15) 0.0418(6) Uani 1 1 d . . .
O2 O 0.0947(3) 0.2004(2) 0.27182(17) 0.0528(7) Uani 1 1 d . . .
O3 O 0.6775(3) 0.3609(2) 0.19999(16) 0.0534(7) Uani 1 1 d . . .
O4 O 0.9134(3) 0.45500(19) 0.32744(14) 0.0403(6) Uani 1 1 d . . .
N1 N 0.4217(3) 0.3228(2) 0.70484(18) 0.0335(7) Uani 1 1 d . . .
N2 N 0.3284(3) 0.3001(2) 0.59648(18) 0.0322(7) Uani 1 1 d . . .
H2N H 0.2033 0.2725 0.5760 0.039 Uiso 1 1 calc R . .
N3 N 0.1501(4) 0.2311(2) 0.3683(2) 0.0375(7) Uani 1 1 d . . .
N4 N 0.7513(4) 0.3965(2) 0.2944(2) 0.0370(7) Uani 1 1 d . . .
C1 C 0.2332(5) 0.1673(3) 0.9673(3) 0.0461(9) Uani 1 1 d . . .
C2 C 0.1542(6) 0.0499(4) 0.9081(3) 0.0510(13) Uani 0.829(3) 1 d P A 1
H2 H 0.0285 0.0122 0.9071 0.061 Uiso 0.829(3) 1 calc PR A 1
C3 C 0.2756(6) 0.0008(4) 0.8558(3) 0.0501(13) Uani 0.829(3) 1 d P A 1
H3 H 0.2466 -0.0752 0.8132 0.060 Uiso 0.829(3) 1 calc PR A 1
C4 C 0.4633(5) 0.0796(3) 0.8720(3) 0.0414(11) Uani 0.829(3) 1 d P A 1
H4A H 0.4830 0.1020 0.8025 0.050 Uiso 0.829(3) 1 calc PR A 1
H4B H 0.5787 0.0372 0.9097 0.050 Uiso 0.829(3) 1 calc PR A 1
C2' C 0.259(3) 0.1443(15) 1.0611(14) 0.032(5) Uiso 0.171(3) 1 d P A 2
H2' H 0.1598 0.1299 1.0980 0.038 Uiso 0.171(3) 1 calc PR A 2
C3' C 0.445(4) 0.144(3) 1.099(2) 0.131(11) Uiso 0.171(3) 1 d P A 2
H3' H 0.5047 0.1230 1.1691 0.157 Uiso 0.171(3) 1 calc PR A 2
C4' C 0.565(2) 0.1793(15) 1.0215(12) 0.029(5) Uiso 0.171(3) 1 d P A 2
H4'1 H 0.6468 0.2569 1.0479 0.035 Uiso 0.171(3) 1 calc PR A 2
H4'2 H 0.6511 0.1143 1.0096 0.035 Uiso 0.171(3) 1 calc PR A 2
C5 C 0.4348(5) 0.1912(3) 0.9395(3) 0.0426(9) Uani 1 1 d . A .
C6 C 0.4205(4) 0.3148(3) 0.8871(2) 0.0381(9) Uani 1 1 d . . .
H6 H 0.5535 0.3596 0.8998 0.046 Uiso 1 1 calc R A .
C7 C 0.2899(4) 0.3811(3) 0.9483(2) 0.0441(9) Uani 1 1 d . A .
H7A H 0.3623 0.4042 1.0240 0.053 Uiso 1 1 calc R . .
H7B H 0.2411 0.4553 0.9141 0.053 Uiso 1 1 calc R . .
C8 C 0.1198(4) 0.2839(3) 0.9398(2) 0.0414(9) Uani 1 1 d . A .
C9 C -0.0046(5) 0.3134(3) 1.0172(2) 0.0630(11) Uani 1 1 d . . .
H9A H -0.0791 0.3844 0.9954 0.095 Uiso 1 1 calc R A .
H9B H 0.0819 0.3319 1.0897 0.095 Uiso 1 1 calc R . .
H9C H -0.0968 0.2429 1.0163 0.095 Uiso 1 1 calc R . .
C10 C -0.0070(4) 0.2750(3) 0.8246(2) 0.0525(10) Uani 1 1 d . . .
H10A H -0.0701 0.3530 0.8119 0.063 Uiso 1 1 calc R A .
H10B H -0.1138 0.2096 0.8161 0.063 Uiso 1 1 calc R . .
C11 C 0.1029(4) 0.2486(3) 0.7384(2) 0.0459(10) Uani 1 1 d . A .
H11A H 0.0970 0.1590 0.7216 0.055 Uiso 1 1 calc R . .
H11B H 0.0340 0.2847 0.6723 0.055 Uiso 1 1 calc R . .
C12 C 0.3160(4) 0.2978(3) 0.7702(2) 0.0350(8) Uani 1 1 d . A .
C13 C 0.4282(4) 0.3201(3) 0.5226(2) 0.0308(8) Uani 1 1 d . . .
C14 C 0.6244(4) 0.3738(3) 0.5545(2) 0.0299(8) Uani 1 1 d . . .
H14 H 0.6852 0.3934 0.6286 0.036 Uiso 1 1 calc R . .
C15 C 0.7278(4) 0.3981(3) 0.4824(2) 0.0305(8) Uani 1 1 d . . .
H15 H 0.8592 0.4344 0.5061 0.037 Uiso 1 1 calc R . .
C16 C 0.6405(4) 0.3693(3) 0.3726(2) 0.0311(8) Uani 1 1 d . . .
C17 C 0.4531(4) 0.3155(3) 0.3375(2) 0.0316(8) Uani 1 1 d . . .
H17 H 0.3958 0.2947 0.2632 0.038 Uiso 1 1 calc R . .
C18 C 0.3470(4) 0.2914(3) 0.4114(2) 0.0297(8) Uani 1 1 d . . .
C1S C 0.6031(6) 1.0181(3) 0.6058(3) 0.0587(11) Uani 1 1 d . . .
H1S H 0.6747 1.0306 0.6791 0.070 Uiso 1 1 calc R . .
C2S C 0.4045(6) 0.9797(3) 0.5784(3) 0.0575(10) Uani 1 1 d . . .
H2S H 0.3393 0.9660 0.6329 0.069 Uiso 1 1 calc R . .
C3S C 0.3025(5) 0.9616(3) 0.4736(4) 0.0563(11) Uani 1 1 d . . .
H3S H 0.1661 0.9350 0.4548 0.068 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_3
C12 N1 N2 116.1(2) .
C13 N2 N1 120.4(2) .
O2 N3 O1 122.4(3) .
O2 N3 C18 118.4(3) .
O1 N3 C18 119.2(2) .
O3 N4 O4 123.8(3) .
O3 N4 C16 118.3(3) .
O4 N4 C16 117.9(2) .
C2' C1 C2 102.7(8) .
C2' C1 C8 113.8(9) .
C2 C1 C8 119.7(3) .
C2' C1 C5 111.0(9) .
C2 C1 C5 103.6(3) .
C8 C1 C5 105.6(3) .
C3 C2 C1 113.3(4) .
C2 C3 C4 111.9(4) .
C3 C4 C5 104.1(3) .
C1 C2' C3' 106(2) .
C2' C3' C4' 114(3) .
C5 C4' C3' 102.2(17) .
C4' C5 C4 99.1(8) .
C4' C5 C6 120.7(8) .
C4 C5 C6 117.2(3) .
C4' C5 C1 106.6(8) .
C4 C5 C1 107.0(3) .
C6 C5 C1 105.3(3) .
C12 C6 C7 109.4(3) .
C12 C6 C5 111.8(3) .
C7 C6 C5 100.4(2) .
C8 C7 C6 102.3(3) .
C9 C8 C10 110.3(3) .
C9 C8 C7 113.1(3) .
C10 C8 C7 107.0(3) .
C9 C8 C1 111.6(3) .
C10 C8 C1 112.8(3) .
C7 C8 C1 101.8(2) .
C8 C10 C11 115.4(3) .
C12 C11 C10 113.9(3) .
N1 C12 C6 116.0(3) .
N1 C12 C11 125.7(3) .
C6 C12 C11 118.2(3) .
N2 C13 C18 123.5(3) .
N2 C13 C14 120.2(3) .
C18 C13 C14 116.3(3) .
C15 C14 C13 121.9(3) .
C14 C15 C16 119.8(3) .
C17 C16 C15 120.8(3) .
C17 C16 N4 119.3(3) .
C15 C16 N4 119.9(3) .
C16 C17 C18 119.3(3) .
C17 C18 C13 121.8(3) .
C17 C18 N3 116.3(3) .
C13 C18 N3 121.9(3) .
C2S C1S C3S 119.9(3) 2_676
C3S C2S C1S 120.0(3) .
C2S C3S C1S 120.1(3) 2_676
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N3 1.244(3) .
O2 N3 1.227(3) .
O3 N4 1.226(3) .
O4 N4 1.234(3) .
N1 C12 1.293(3) .
N1 N2 1.387(3) .
N2 C13 1.345(3) .
N3 C18 1.455(3) .
N4 C16 1.463(3) .
C1 C2' 1.228(17) .
C1 C2 1.459(5) .
C1 C8 1.558(4) .
C1 C5 1.559(4) .
C2 C3 1.330(5) .
C3 C4 1.497(5) .
C4 C5 1.509(4) .
C2' C3' 1.28(3) .
C3' C4' 1.52(3) .
C4' C5 1.230(15) .
C5 C6 1.557(4) .
C6 C12 1.497(4) .
C6 C7 1.537(4) .
C7 C8 1.535(4) .
C8 C9 1.518(4) .
C8 C10 1.522(4) .
C10 C11 1.531(4) .
C11 C12 1.505(4) .
C13 C18 1.413(4) .
C13 C14 1.415(4) .
C14 C15 1.352(4) .
C15 C16 1.403(4) .
C16 C17 1.364(3) .
C17 C18 1.384(4) .
C1S C2S 1.382(4) .
C1S C3S 1.381(4) 2_676
C2S C3S 1.358(4) .
C3S C1S 1.381(4) 2_676
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_4
C12 N1 N2 C13 -178.1(3) . .
C2' C1 C2 C3 -113.2(9) . .
C8 C1 C2 C3 119.6(4) . .
C5 C1 C2 C3 2.4(4) . .
C1 C2 C3 C4 0.2(5) . .
C2 C3 C4 C5 -2.9(4) . .
C2 C1 C2' C3' 107.4(18) . .
C8 C1 C2' C3' -121.7(18) . .
C5 C1 C2' C3' -3(2) . .
C1 C2' C3' C4' 4(3) . .
C2' C3' C4' C5 -4(3) . .
C3' C4' C5 C4 -108.9(14) . .
C3' C4' C5 C6 121.8(14) . .
C3' C4' C5 C1 2.0(16) . .
C3 C4 C5 C4' 114.8(8) . .
C3 C4 C5 C6 -113.7(3) . .
C3 C4 C5 C1 4.2(4) . .
C2' C1 C5 C4' 0.3(12) . .
C2 C1 C5 C4' -109.3(9) . .
C8 C1 C5 C4' 124.0(9) . .
C2' C1 C5 C4 105.5(9) . .
C2 C1 C5 C4 -4.1(4) . .
C8 C1 C5 C4 -130.7(3) . .
C2' C1 C5 C6 -129.0(9) . .
C2 C1 C5 C6 121.3(3) . .
C8 C1 C5 C6 -5.3(3) . .
C4' C5 C6 C12 156.2(9) . .
C4 C5 C6 C12 35.5(4) . .
C1 C5 C6 C12 -83.3(3) . .
C4' C5 C6 C7 -87.8(9) . .
C4 C5 C6 C7 151.4(3) . .
C1 C5 C6 C7 32.6(3) . .
C12 C6 C7 C8 69.1(3) . .
C5 C6 C7 C8 -48.6(3) . .
C6 C7 C8 C9 165.4(3) . .
C6 C7 C8 C10 -72.9(3) . .
C6 C7 C8 C1 45.6(3) . .
C2' C1 C8 C9 -23.2(9) . .
C2 C1 C8 C9 98.7(4) . .
C5 C1 C8 C9 -145.2(3) . .
C2' C1 C8 C10 -148.0(9) . .
C2 C1 C8 C10 -26.1(4) . .
C5 C1 C8 C10 90.0(3) . .
C2' C1 C8 C7 97.7(9) . .
C2 C1 C8 C7 -140.4(3) . .
C5 C1 C8 C7 -24.3(3) . .
C9 C8 C10 C11 178.6(3) . .
C7 C8 C10 C11 55.2(4) . .
C1 C8 C10 C11 -55.9(4) . .
C8 C10 C11 C12 -30.0(4) . .
N2 N1 C12 C6 176.3(3) . .
N2 N1 C12 C11 -1.0(4) . .
C7 C6 C12 N1 135.3(3) . .
C5 C6 C12 N1 -114.4(3) . .
C7 C6 C12 C11 -47.3(4) . .
C5 C6 C12 C11 63.1(4) . .
C10 C11 C12 N1 -156.7(3) . .
C10 C11 C12 C6 26.1(4) . .
N1 N2 C13 C18 175.6(3) . .
N1 N2 C13 C14 -5.1(4) . .
N2 C13 C14 C15 -178.4(3) . .
C18 C13 C14 C15 0.9(4) . .
C13 C14 C15 C16 -0.2(4) . .
C14 C15 C16 C17 -0.9(5) . .
C14 C15 C16 N4 179.4(3) . .
O3 N4 C16 C17 -5.8(4) . .
O4 N4 C16 C17 173.6(3) . .
O3 N4 C16 C15 173.9(3) . .
O4 N4 C16 C15 -6.7(4) . .
C15 C16 C17 C18 1.3(5) . .
N4 C16 C17 C18 -179.0(3) . .
C16 C17 C18 C13 -0.6(5) . .
C16 C17 C18 N3 -178.5(3) . .
N2 C13 C18 C17 178.8(3) . .
C14 C13 C18 C17 -0.5(4) . .
N2 C13 C18 N3 -3.4(4) . .
C14 C13 C18 N3 177.3(3) . .
O2 N3 C18 C17 3.4(4) . .
O1 N3 C18 C17 -175.3(3) . .
O2 N3 C18 C13 -174.5(3) . .
O1 N3 C18 C13 6.8(4) . .
C3S C1S C2S C3S 0.2(6) 2_676 .
C1S C2S C3S C1S -0.2(6) . 2_676
