#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/66/7106654.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_7106654
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         'C21 H15 N O5'
_chemical_formula_sum            'C21 H15 N O5'
_chemical_formula_weight         361.34
_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                97.856(18)
_cell_angle_beta                 96.761(13)
_cell_angle_gamma                104.70(2)
_cell_formula_units_Z            2
_cell_length_a                   9.119(8)
_cell_length_b                   9.581(7)
_cell_length_c                   10.232(8)
_cell_measurement_reflns_used    2987
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.3
_cell_volume                     845.7(12)
_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      93(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_sigmaI/netI    0.0729
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5292
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.8540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0783
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1425P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1996
_refine_ls_wR_factor_ref         0.2115
_reflns_number_gt                2529
_reflns_number_total             2969
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc12720a.txt
_cod_data_source_block           10
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7106654
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
C1 C 0.3206(2) 0.0413(2) 0.3664(2) 0.0241(5) Uani 1 1 d . . .
C2 C 0.4686(2) 0.1418(2) 0.4078(2) 0.0241(5) Uani 1 1 d . . .
C3 C 0.4886(3) 0.2711(2) 0.5017(2) 0.0268(5) Uani 1 1 d . . .
H3A H 0.5872 0.3383 0.5309 0.032 Uiso 1 1 calc R . .
C4 C 0.3622(3) 0.2962(2) 0.5489(2) 0.0263(5) Uani 1 1 d . . .
O4 O 0.34997(18) 0.41301(16) 0.63811(16) 0.0334(5) Uani 1 1 d . . .
C5 C 0.2174(2) 0.1953(2) 0.5108(2) 0.0250(5) Uani 1 1 d . . .
O5 O 0.11154(17) 0.24665(15) 0.57478(15) 0.0316(5) Uani 1 1 d . . .
C6 C 0.1942(2) 0.0673(2) 0.4229(2) 0.0249(5) Uani 1 1 d . . .
H6A H 0.0959 -0.0017 0.4006 0.030 Uiso 1 1 calc R . .
C7 C 0.2920(2) -0.0864(2) 0.2563(2) 0.0244(5) Uani 1 1 d . . .
C8 C 0.3366(2) -0.0679(2) 0.1321(2) 0.0258(5) Uani 1 1 d . . .
H8A H 0.3893 0.0270 0.1188 0.031 Uiso 1 1 calc R . .
C9 C 0.3050(3) -0.1861(2) 0.0276(2) 0.0304(5) Uani 1 1 d . . .
H9A H 0.3373 -0.1720 -0.0557 0.036 Uiso 1 1 calc R . .
C10 C 0.2258(3) -0.3249(2) 0.0459(2) 0.0316(6) Uani 1 1 d . . .
H10A H 0.2041 -0.4061 -0.0248 0.038 Uiso 1 1 calc R . .
C11 C 0.1787(3) -0.3441(2) 0.1681(2) 0.0325(6) Uani 1 1 d . . .
H11A H 0.1238 -0.4387 0.1804 0.039 Uiso 1 1 calc R . .
C12 C 0.2109(2) -0.2268(2) 0.2716(2) 0.0272(5) Uani 1 1 d . . .
H12A H 0.1777 -0.2416 0.3545 0.033 Uiso 1 1 calc R . .
C13 C 0.5999(2) 0.1089(2) 0.3539(2) 0.0250(5) Uani 1 1 d . . .
H13A H 0.5932 0.0109 0.3156 0.030 Uiso 1 1 calc R . .
N14 N 0.7241(2) 0.20981(18) 0.35735(18) 0.0276(5) Uani 1 1 d . . .
O15 O 0.82894(16) 0.13897(15) 0.29719(15) 0.0276(4) Uani 1 1 d . . .
C16 C 0.9446(2) 0.2361(2) 0.2589(2) 0.0249(5) Uani 1 1 d . . .
O16 O 0.97745(19) 0.36635(15) 0.28398(18) 0.0387(5) Uani 1 1 d . . .
O17 O 1.01293(17) 0.15219(14) 0.18584(15) 0.0284(4) Uani 1 1 d . . .
C18 C 1.1316(2) 0.2180(2) 0.1170(2) 0.0252(5) Uani 1 1 d . . .
C19 C 1.1028(3) 0.1775(2) -0.0200(2) 0.0284(5) Uani 1 1 d . . .
H19A H 1.0041 0.1200 -0.0640 0.034 Uiso 1 1 calc R . .
C20 C 1.2203(3) 0.2220(2) -0.0929(2) 0.0314(6) Uani 1 1 d . . .
H20A H 1.2030 0.1926 -0.1872 0.038 Uiso 1 1 calc R . .
C21 C 1.3626(3) 0.3090(2) -0.0283(2) 0.0328(6) Uani 1 1 d . . .
H21A H 1.4428 0.3402 -0.0781 0.039 Uiso 1 1 calc R . .
C22 C 1.3880(3) 0.3508(2) 0.1104(2) 0.0313(6) Uani 1 1 d . . .
H22A H 1.4855 0.4110 0.1546 0.038 Uiso 1 1 calc R . .
C23 C 1.2719(3) 0.3053(2) 0.1844(2) 0.0283(5) Uani 1 1 d . . .
H23A H 1.2886 0.3335 0.2789 0.034 Uiso 1 1 calc R . .
C24 C 0.1878(3) 0.3979(2) 0.6279(2) 0.0336(6) Uani 1 1 d . . .
H24A H 0.1610 0.4258 0.7170 0.040 Uiso 1 1 calc R . .
H24B H 0.1569 0.4617 0.5678 0.040 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
C6 C1 C2 119.88(19) . . ?
C6 C1 C7 118.26(18) . . ?
C2 C1 C7 121.69(19) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 C13 120.50(18) . . ?
C1 C2 C13 119.15(19) . . ?
C4 C3 C2 118.04(19) . . ?
C4 C3 H3A 121.0 . . ?
C2 C3 H3A 121.0 . . ?
C3 C4 O4 129.5(2) . . ?
C3 C4 C5 121.5(2) . . ?
O4 C4 C5 108.92(19) . . ?
C4 O4 C24 105.03(16) . . ?
C6 C5 O5 128.53(19) . . ?
C6 C5 C4 122.1(2) . . ?
O5 C5 C4 109.41(19) . . ?
C5 O5 C24 104.86(17) . . ?
C5 C6 C1 118.01(19) . . ?
C5 C6 H6A 121.0 . . ?
C1 C6 H6A 121.0 . . ?
C8 C7 C12 118.05(19) . . ?
C8 C7 C1 121.00(18) . . ?
C12 C7 C1 120.8(2) . . ?
C9 C8 C7 121.12(19) . . ?
C9 C8 H8A 119.4 . . ?
C7 C8 H8A 119.4 . . ?
C8 C9 C10 119.7(2) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C11 C12 C7 121.0(2) . . ?
C11 C12 H12A 119.5 . . ?
C7 C12 H12A 119.5 . . ?
N14 C13 C2 121.21(19) . . ?
N14 C13 H13A 119.4 . . ?
C2 C13 H13A 119.4 . . ?
C13 N14 O15 106.46(17) . . ?
C16 O15 N14 112.02(16) . . ?
O16 C16 O17 128.0(2) . . ?
O16 C16 O15 127.8(2) . . ?
O17 C16 O15 104.19(17) . . ?
C16 O17 C18 119.93(16) . . ?
C19 C18 C23 122.3(2) . . ?
C19 C18 O17 115.66(19) . . ?
C23 C18 O17 121.7(2) . . ?
C18 C19 C20 119.0(2) . . ?
C18 C19 H19A 120.5 . . ?
C20 C19 H19A 120.5 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20A 120.0 . . ?
C19 C20 H20A 120.0 . . ?
C20 C21 C22 119.8(2) . . ?
C20 C21 H21A 120.1 . . ?
C22 C21 H21A 120.1 . . ?
C23 C22 C21 120.7(2) . . ?
C23 C22 H22A 119.7 . . ?
C21 C22 H22A 119.7 . . ?
C18 C23 C22 118.1(2) . . ?
C18 C23 H23A 120.9 . . ?
C22 C23 H23A 120.9 . . ?
O5 C24 O4 106.60(17) . . ?
O5 C24 H24A 110.4 . . ?
O4 C24 H24A 110.4 . . ?
O5 C24 H24B 110.4 . . ?
O4 C24 H24B 110.4 . . ?
H24A C24 H24B 108.6 . . ?
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
C1 C6 1.410(3) . ?
C1 C2 1.422(3) . ?
C1 C7 1.492(3) . ?
C2 C3 1.417(3) . ?
C2 C13 1.463(3) . ?
C3 C4 1.365(3) . ?
C3 H3A 0.9500 . ?
C4 O4 1.380(3) . ?
C4 C5 1.399(3) . ?
O4 C24 1.439(3) . ?
C5 C6 1.371(3) . ?
C5 O5 1.379(3) . ?
O5 C24 1.437(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.400(3) . ?
C7 C12 1.401(3) . ?
C8 C9 1.392(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.392(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.389(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.381(3) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 N14 1.282(3) . ?
C13 H13A 0.9500 . ?
N14 O15 1.451(2) . ?
O15 C16 1.353(3) . ?
C16 O16 1.191(3) . ?
C16 O17 1.339(3) . ?
O17 C18 1.421(3) . ?
C18 C19 1.378(3) . ?
C18 C23 1.380(3) . ?
C19 C20 1.389(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.384(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.396(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.389(3) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
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
C6 C1 C2 C3 -2.5(3) . . . . ?
C7 C1 C2 C3 172.70(18) . . . . ?
C6 C1 C2 C13 176.51(18) . . . . ?
C7 C1 C2 C13 -8.3(3) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C13 C2 C3 C4 -179.84(19) . . . . ?
C2 C3 C4 O4 -178.90(19) . . . . ?
C2 C3 C4 C5 2.6(3) . . . . ?
C3 C4 O4 C24 167.5(2) . . . . ?
C5 C4 O4 C24 -13.9(2) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
O4 C4 C5 C6 -179.78(19) . . . . ?
C3 C4 C5 O5 178.96(19) . . . . ?
O4 C4 C5 O5 0.2(2) . . . . ?
C6 C5 O5 C24 -166.4(2) . . . . ?
C4 C5 O5 C24 13.6(2) . . . . ?
O5 C5 C6 C1 177.67(19) . . . . ?
C4 C5 C6 C1 -2.4(3) . . . . ?
C2 C1 C6 C5 4.0(3) . . . . ?
C7 C1 C6 C5 -171.31(18) . . . . ?
C6 C1 C7 C8 123.5(2) . . . . ?
C2 C1 C7 C8 -51.8(3) . . . . ?
C6 C1 C7 C12 -52.4(3) . . . . ?
C2 C1 C7 C12 132.4(2) . . . . ?
C12 C7 C8 C9 -1.7(3) . . . . ?
C1 C7 C8 C9 -177.64(19) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C7 -0.2(3) . . . . ?
C8 C7 C12 C11 1.3(3) . . . . ?
C1 C7 C12 C11 177.28(19) . . . . ?
C3 C2 C13 N14 -20.5(3) . . . . ?
C1 C2 C13 N14 160.5(2) . . . . ?
C2 C13 N14 O15 179.55(17) . . . . ?
C13 N14 O15 C16 161.75(18) . . . . ?
N14 O15 C16 O16 10.2(3) . . . . ?
N14 O15 C16 O17 -169.47(14) . . . . ?
O16 C16 O17 C18 -6.1(3) . . . . ?
O15 C16 O17 C18 173.59(17) . . . . ?
C16 O17 C18 C19 -118.7(2) . . . . ?
C16 O17 C18 C23 67.4(3) . . . . ?
C23 C18 C19 C20 2.1(3) . . . . ?
O17 C18 C19 C20 -171.75(18) . . . . ?
C18 C19 C20 C21 -1.7(3) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C19 C18 C23 C22 -1.2(3) . . . . ?
O17 C18 C23 C22 172.26(18) . . . . ?
C21 C22 C23 C18 0.0(3) . . . . ?
C5 O5 C24 O4 -22.0(2) . . . . ?
C4 O4 C24 O5 22.2(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653315
