#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/38/1503894.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_1503894
loop_
_publ_author_name
'Yi, Chenyi'
'Blum, Carmen'
'Liu, Shi-Xia'
'Keene, Tony D.'
'Frei, Gabriela'
'Neels, Antonia'
'Decurtins, Silvio'
_publ_section_title
;
 Isolable zwitterionic pyridinio-semiquinone pi-radicals. Mild and
 efficient single-step access to stable radicals.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2261
_journal_page_last               2264
_journal_paper_doi               10.1021/ol900559p
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C16 H12 N3 O4'
_chemical_formula_weight         310.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 98.293(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3879(8)
_cell_length_b                   12.146(2)
_cell_length_c                   19.036(2)
_cell_measurement_reflns_used    5538
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.93
_cell_measurement_theta_min      2.00
_cell_volume                     1461.5(3)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_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  0.1148
_diffrn_reflns_av_sigmaI/netI    0.0803
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16994
_diffrn_reflns_theta_full        25.17
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       0.036(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1433
_refine_ls_R_factor_gt           0.0983
_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)+(0.1598P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2605
_refine_ls_wR_factor_ref         0.2763
_reflns_number_gt                1246
_reflns_number_total             2605
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900559p_si_004.cif
_cod_data_source_block           y321
_cod_original_cell_volume        1461.5(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1503894
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.8038(8) 0.4366(4) 0.4996(3) 0.0545(13) Uani 1 1 d .
C2 C 0.8349(8) 0.3878(4) 0.4310(3) 0.0533(13) Uani 1 1 d .
C3 C 0.8169(8) 0.4517(4) 0.3713(3) 0.0571(13) Uani 1 1 d .
C4 C 0.7621(8) 0.5665(4) 0.3684(3) 0.0583(13) Uani 1 1 d .
C5 C 0.7260(8) 0.6138(4) 0.4354(3) 0.0541(13) Uani 1 1 d .
C6 C 0.7430(8) 0.5514(4) 0.4969(3) 0.0550(13) Uani 1 1 d .
C7 C 0.8043(9) 0.1962(4) 0.4670(3) 0.0621(14) Uani 1 1 d .
H7A H 0.6574 0.2147 0.4736 0.075 Uiso 1 1 calc R
H7B H 0.8906 0.1885 0.5142 0.075 Uiso 1 1 calc R
C8 C 0.8088(10) 0.0905(5) 0.4248(3) 0.0695(16) Uani 1 1 d .
H8A H 0.9552 0.0776 0.4153 0.083 Uiso 1 1 calc R
H8B H 0.7696 0.0285 0.4540 0.083 Uiso 1 1 calc R
C9 C 0.4538(11) 0.0756(5) 0.3659(4) 0.0810(18) Uani 1 1 d .
H9A H 0.4336 0.0026 0.3858 0.121 Uiso 1 1 calc R
H9B H 0.3687 0.0816 0.3189 0.121 Uiso 1 1 calc R
H9C H 0.4092 0.1322 0.3973 0.121 Uiso 1 1 calc R
C10 C 0.7157(9) 0.3167(5) 0.2786(3) 0.0634(15) Uani 1 1 d .
H10A H 0.6060 0.2927 0.3037 0.076 Uiso 1 1 calc R
C11 C 0.7444(10) 0.2669(5) 0.2160(3) 0.0701(16) Uani 1 1 d .
H11A H 0.6530 0.2090 0.1973 0.084 Uiso 1 1 calc R
C12 C 0.9052(10) 0.3007(5) 0.1805(3) 0.0695(16) Uani 1 1 d .
H12A H 0.9292 0.2644 0.1382 0.083 Uiso 1 1 calc R
C13 C 1.0323(10) 0.3878(5) 0.2066(3) 0.0695(16) Uani 1 1 d .
H13A H 1.1407 0.4136 0.1814 0.083 Uiso 1 1 calc R
C14 C 1.0005(9) 0.4372(5) 0.2696(3) 0.0614(14) Uani 1 1 d .
H14A H 1.0880 0.4966 0.2882 0.074 Uiso 1 1 calc R
C15 C 0.6752(9) 0.7282(5) 0.4367(3) 0.0614(14) Uani 1 1 d .
C16 C 0.6937(8) 0.5981(4) 0.5614(3) 0.0578(14) Uani 1 1 d .
N1 N 0.8459(7) 0.4011(3) 0.3045(2) 0.0582(12) Uani 1 1 d .
N2 N 0.6380(8) 0.8205(4) 0.4384(3) 0.0737(14) Uani 1 1 d .
N3 N 0.6513(7) 0.6373(4) 0.6128(3) 0.0654(13) Uani 1 1 d .
O1 O 0.8280(5) 0.3815(3) 0.55592(19) 0.0586(10) Uani 1 1 d .
O2 O 0.8916(6) 0.2816(3) 0.42580(19) 0.0606(10) Uani 1 1 d .
O3 O 0.6723(7) 0.0908(3) 0.3596(2) 0.0778(13) Uani 1 1 d .
O4 O 0.7375(6) 0.6205(3) 0.3121(2) 0.0667(11) 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 0.0016 '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
O1 C1 C6 123.0(5)
O1 C1 C2 121.8(5)
C6 C1 C2 115.2(5)
O2 C2 C3 118.2(5)
O2 C2 C1 121.5(4)
C3 C2 C1 120.2(5)
C2 C3 C4 125.0(5)
C2 C3 N1 118.9(5)
C4 C3 N1 116.0(5)
O4 C4 C3 122.9(5)
O4 C4 C5 122.2(5)
C3 C4 C5 114.8(5)
C6 C5 C15 120.5(5)
C6 C5 C4 121.6(5)
C15 C5 C4 117.9(5)
C5 C6 C16 120.6(5)
C5 C6 C1 123.1(5)
C16 C6 C1 116.3(5)
O2 C7 C8 106.2(4)
O2 C7 H7A 110.5
C8 C7 H7A 110.5
O2 C7 H7B 110.5
C8 C7 H7B 110.5
H7A C7 H7B 108.7
O3 C8 C7 114.0(5)
O3 C8 H8A 108.7
C7 C8 H8A 108.7
O3 C8 H8B 108.7
C7 C8 H8B 108.7
H8A C8 H8B 107.6
O3 C9 H9A 109.5
O3 C9 H9B 109.5
H9A C9 H9B 109.5
O3 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N1 C10 C11 119.6(5)
N1 C10 H10A 120.2
C11 C10 H10A 120.2
C12 C11 C10 119.9(6)
C12 C11 H11A 120.0
C10 C11 H11A 120.0
C11 C12 C13 119.7(6)
C11 C12 H12A 120.1
C13 C12 H12A 120.1
C12 C13 C14 119.4(6)
C12 C13 H13A 120.3
C14 C13 H13A 120.3
N1 C14 C13 120.0(5)
N1 C14 H14A 120.0
C13 C14 H14A 120.0
N2 C15 C5 178.8(6)
N3 C16 C6 178.7(6)
C14 N1 C10 121.3(5)
C14 N1 C3 119.5(4)
C10 N1 C3 119.2(5)
C2 O2 C7 120.9(4)
C8 O3 C9 114.5(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.253(6)
C1 C6 1.446(7)
C1 C2 1.473(7)
C2 O2 1.347(6)
C2 C3 1.368(7)
C3 C4 1.437(7)
C3 N1 1.449(7)
C4 O4 1.246(6)
C4 C5 1.448(8)
C5 C6 1.386(7)
C5 C15 1.427(8)
C6 C16 1.429(8)
C7 O2 1.459(6)
C7 C8 1.517(8)
C7 H7A 0.9900
C7 H7B 0.9900
C8 O3 1.409(7)
C8 H8A 0.9900
C8 H8B 0.9900
C9 O3 1.430(7)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 N1 1.366(7)
C10 C11 1.371(8)
C10 H10A 0.9500
C11 C12 1.371(9)
C11 H11A 0.9500
C12 C13 1.381(8)
C12 H12A 0.9500
C13 C14 1.382(8)
C13 H13A 0.9500
C14 N1 1.341(7)
C14 H14A 0.9500
C15 N2 1.147(7)
C16 N3 1.155(7)
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
O1 C1 C2 O2 -0.3(7)
C6 C1 C2 O2 -180.0(4)
O1 C1 C2 C3 -176.9(5)
C6 C1 C2 C3 3.4(7)
O2 C2 C3 C4 -178.7(5)
C1 C2 C3 C4 -2.0(8)
O2 C2 C3 N1 4.0(7)
C1 C2 C3 N1 -179.3(5)
C2 C3 C4 O4 -176.4(5)
N1 C3 C4 O4 0.9(7)
C2 C3 C4 C5 0.4(7)
N1 C3 C4 C5 177.7(4)
O4 C4 C5 C6 176.5(5)
C3 C4 C5 C6 -0.3(7)
O4 C4 C5 C15 -4.4(7)
C3 C4 C5 C15 178.7(5)
C15 C5 C6 C16 5.0(8)
C4 C5 C6 C16 -176.0(5)
C15 C5 C6 C1 -177.0(5)
C4 C5 C6 C1 2.0(8)
O1 C1 C6 C5 176.8(5)
C2 C1 C6 C5 -3.5(7)
O1 C1 C6 C16 -5.1(7)
C2 C1 C6 C16 174.6(4)
O2 C7 C8 O3 -66.3(6)
N1 C10 C11 C12 1.1(9)
C10 C11 C12 C13 -2.6(9)
C11 C12 C13 C14 2.4(9)
C12 C13 C14 N1 -0.7(8)
C6 C5 C15 N2 74(30)
C4 C5 C15 N2 -105(30)
C5 C6 C16 N3 24(25)
C1 C6 C16 N3 -154(25)
C13 C14 N1 C10 -0.9(8)
C13 C14 N1 C3 178.6(5)
C11 C10 N1 C14 0.7(8)
C11 C10 N1 C3 -178.8(5)
C2 C3 N1 C14 -119.9(6)
C4 C3 N1 C14 62.6(6)
C2 C3 N1 C10 59.6(7)
C4 C3 N1 C10 -117.9(5)
C3 C2 O2 C7 -144.4(5)
C1 C2 O2 C7 38.9(7)
C8 C7 O2 C2 152.6(4)
C7 C8 O3 C9 -76.3(6)
