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#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/66/7106653.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.
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data_7106653
loop_
_publ_author_name
'Roy T. McBurney'
'Alexandra M. Z. Slawin'
'Laura A. Smart'
'Yanping Yu'
'John C. Walton'
_publ_section_title
;
 UV Promoted Phenanthridine Syntheses from Oxime Carbonate Derived Iminyl
 Radicals
;
_journal_name_full               'Chem. Commun.'
_journal_page_first              7974
_journal_paper_doi               10.1039/c1cc12720a
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C14 H10 N2 O2'
_chemical_formula_sum            'C14 H10 N2 O2'
_chemical_formula_weight         238.24
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.36(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.469(3)
_cell_length_b                   13.268(10)
_cell_length_c                   18.459(16)
_cell_measurement_reflns_used    1066
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.5
_cell_measurement_theta_min      21.6
_cell_volume                     1087.8(14)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1630
_diffrn_reflns_av_sigmaI/netI    0.0708
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13762
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         4.11
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       Prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.028(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.244
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.244
_refine_ls_R_factor_all          0.1570
_refine_ls_R_factor_gt           0.1223
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3345
_refine_ls_wR_factor_ref         0.3712
_reflns_number_gt                1317
_reflns_number_total             1978
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc12720a.txt
_cod_data_source_block           5d
_cod_original_cell_volume        1087.8(15)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7106653
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_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 0.0596(8) 0.6289(3) 0.1786(2) 0.0666(12) Uani 1 1 d . . .
C1A C -0.0102(10) 0.7068(3) 0.2229(2) 0.0653(13) Uani 1 1 d . . .
C2 C -0.1904(10) 0.6829(3) 0.2779(2) 0.0670(13) Uani 1 1 d . . .
H2A H -0.2560 0.6155 0.2835 0.080 Uiso 1 1 calc R . .
C3 C -0.2721(11) 0.7567(3) 0.3239(2) 0.0676(13) Uani 1 1 d . . .
N3 N -0.4641(9) 0.7314(3) 0.3797(2) 0.0713(12) Uani 1 1 d . . .
O1 O -0.5468(8) 0.6439(3) 0.38422(18) 0.0871(12) Uani 1 1 d . . .
O2 O -0.5311(8) 0.7989(2) 0.42105(18) 0.0828(12) Uani 1 1 d . . .
C4 C -0.1772(11) 0.8561(3) 0.3177(3) 0.0730(14) Uani 1 1 d . . .
H4A H -0.2336 0.9063 0.3503 0.088 Uiso 1 1 calc R . .
C5 C -0.0031(11) 0.8804(3) 0.2645(2) 0.0693(13) Uani 1 1 d . . .
H5A H 0.0599 0.9482 0.2598 0.083 Uiso 1 1 calc R . .
C5A C 0.0861(10) 0.8072(3) 0.2160(2) 0.0640(13) Uani 1 1 d . . .
C5B C 0.2703(10) 0.8291(3) 0.1584(2) 0.0656(13) Uani 1 1 d . . .
C6 C 0.3794(10) 0.9258(3) 0.1447(3) 0.0686(13) Uani 1 1 d . . .
H6A H 0.3324 0.9807 0.1745 0.082 Uiso 1 1 calc R . .
C7 C 0.5507(11) 0.9419(3) 0.0896(2) 0.0741(14) Uani 1 1 d . . .
H7A H 0.6219 1.0079 0.0812 0.089 Uiso 1 1 calc R . .
C8 C 0.6237(11) 0.8625(4) 0.0449(3) 0.0741(14) Uani 1 1 d . . .
H8A H 0.7477 0.8744 0.0072 0.089 Uiso 1 1 calc R . .
C9 C 0.5166(11) 0.7680(3) 0.0556(3) 0.0720(14) Uani 1 1 d . . .
H9A H 0.5627 0.7147 0.0243 0.086 Uiso 1 1 calc R . .
C9A C 0.3382(10) 0.7484(3) 0.1125(2) 0.0639(13) Uani 1 1 d . . .
C10 C 0.2223(10) 0.6492(3) 0.1256(3) 0.0674(13) Uani 1 1 d . . .
C11 C 0.2928(11) 0.5632(3) 0.0773(3) 0.0780(14) Uani 1 1 d . . .
H11A H 0.2010 0.5013 0.0935 0.094 Uiso 1 1 calc R . .
H11B H 0.5115 0.5544 0.0801 0.094 Uiso 1 1 calc R . .
H11C H 0.2120 0.5779 0.0269 0.094 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C10 N1 C1A 118.1(4) . . ?
N1 C1A C2 116.6(4) . . ?
N1 C1A C5A 124.4(4) . . ?
C2 C1A C5A 119.1(4) . . ?
C3 C2 C1A 120.0(4) . . ?
C3 C2 H2A 120.0 . . ?
C1A C2 H2A 120.0 . . ?
C2 C3 C4 121.4(5) . . ?
C2 C3 N3 119.5(4) . . ?
C4 C3 N3 119.1(4) . . ?
O1 N3 O2 123.3(4) . . ?
O1 N3 C3 118.4(4) . . ?
O2 N3 C3 118.3(4) . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C5 C5A 121.5(4) . . ?
C4 C5 H5A 119.3 . . ?
C5A C5 H5A 119.3 . . ?
C5 C5A C1A 118.9(4) . . ?
C5 C5A C5B 123.7(4) . . ?
C1A C5A C5B 117.5(4) . . ?
C6 C5B C9A 118.7(4) . . ?
C6 C5B C5A 123.6(4) . . ?
C9A C5B C5A 117.7(4) . . ?
C7 C6 C5B 121.0(4) . . ?
C7 C6 H6A 119.5 . . ?
C5B C6 H6A 119.5 . . ?
C6 C7 C8 120.8(4) . . ?
C6 C7 H7A 119.6 . . ?
C8 C7 H7A 119.6 . . ?
C9 C8 C7 119.9(5) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C8 C9 C9A 120.9(4) . . ?
C8 C9 H9A 119.6 . . ?
C9A C9 H9A 119.6 . . ?
C9 C9A C5B 118.8(4) . . ?
C9 C9A C10 122.3(4) . . ?
C5B C9A C10 118.9(4) . . ?
N1 C10 C9A 123.4(4) . . ?
N1 C10 C11 117.2(4) . . ?
C9A C10 C11 119.4(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
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 C10 1.310(6) . ?
N1 C1A 1.376(5) . ?
C1A C2 1.401(6) . ?
C1A C5A 1.410(6) . ?
C2 C3 1.371(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.394(6) . ?
C3 N3 1.451(6) . ?
N3 O1 1.224(4) . ?
N3 O2 1.236(5) . ?
C4 C5 1.358(6) . ?
C4 H4A 0.9500 . ?
C5 C5A 1.408(6) . ?
C5 H5A 0.9500 . ?
C5A C5B 1.443(6) . ?
C5B C6 1.406(6) . ?
C5B C9A 1.418(6) . ?
C6 C7 1.356(6) . ?
C6 H6A 0.9500 . ?
C7 C8 1.399(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.364(6) . ?
C8 H8A 0.9500 . ?
C9 C9A 1.412(7) . ?
C9 H9A 0.9500 . ?
C9A C10 1.445(6) . ?
C10 C11 1.502(6) . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C1A C2 178.5(4) . . . . ?
C10 N1 C1A C5A -1.2(7) . . . . ?
N1 C1A C2 C3 -179.4(4) . . . . ?
C5A C1A C2 C3 0.4(7) . . . . ?
C1A C2 C3 C4 -0.6(7) . . . . ?
C1A C2 C3 N3 178.7(4) . . . . ?
C2 C3 N3 O1 0.3(7) . . . . ?
C4 C3 N3 O1 179.7(4) . . . . ?
C2 C3 N3 O2 179.0(4) . . . . ?
C4 C3 N3 O2 -1.7(7) . . . . ?
C2 C3 C4 C5 0.8(8) . . . . ?
N3 C3 C4 C5 -178.5(4) . . . . ?
C3 C4 C5 C5A -0.7(7) . . . . ?
C4 C5 C5A C1A 0.5(7) . . . . ?
C4 C5 C5A C5B 179.9(4) . . . . ?
N1 C1A C5A C5 179.4(4) . . . . ?
C2 C1A C5A C5 -0.3(7) . . . . ?
N1 C1A C5A C5B 0.0(7) . . . . ?
C2 C1A C5A C5B -179.7(4) . . . . ?
C5 C5A C5B C6 -0.1(8) . . . . ?
C1A C5A C5B C6 179.3(4) . . . . ?
C5 C5A C5B C9A -178.7(4) . . . . ?
C1A C5A C5B C9A 0.7(7) . . . . ?
C9A C5B C6 C7 -1.1(7) . . . . ?
C5A C5B C6 C7 -179.7(4) . . . . ?
C5B C6 C7 C8 -0.1(7) . . . . ?
C6 C7 C8 C9 1.5(7) . . . . ?
C7 C8 C9 C9A -1.6(7) . . . . ?
C8 C9 C9A C5B 0.4(7) . . . . ?
C8 C9 C9A C10 -179.7(4) . . . . ?
C6 C5B C9A C9 1.0(7) . . . . ?
C5A C5B C9A C9 179.7(4) . . . . ?
C6 C5B C9A C10 -178.9(4) . . . . ?
C5A C5B C9A C10 -0.3(6) . . . . ?
C1A N1 C10 C9A 1.7(7) . . . . ?
C1A N1 C10 C11 -179.3(4) . . . . ?
C9 C9A C10 N1 179.1(4) . . . . ?
C5B C9A C10 N1 -1.0(7) . . . . ?
C9 C9A C10 C11 0.1(7) . . . . ?
C5B C9A C10 C11 180.0(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101885489
