#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/38/1503892.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_1503892
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            'C15 H12 N3 O4'
_chemical_formula_weight         298.28
_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                108.94(4)
_cell_angle_beta                 92.81(4)
_cell_angle_gamma                97.68(4)
_cell_formula_units_Z            2
_cell_length_a                   7.285(4)
_cell_length_b                   9.374(5)
_cell_length_c                   11.100(6)
_cell_measurement_reflns_used    706
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.24
_cell_measurement_theta_min      1.96
_cell_volume                     707.1(7)
_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 0.943
_diffrn_measured_fraction_theta_max 0.943
_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  0.1568
_diffrn_reflns_av_sigmaI/netI    0.4307
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4765
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             310
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .10
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.603
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.603
_refine_ls_R_factor_all          0.2853
_refine_ls_R_factor_gt           0.0758
_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)+(0.0390P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1763
_reflns_number_gt                418
_reflns_number_total             2350
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900559p_si_001.cif
_cod_data_source_block           y264-2
_cod_database_code               1503892
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
C1 C 0.1311(11) 0.0488(9) -0.0832(8) 0.0598(9) Uani 1 1 d .
C2 C 0.1697(11) 0.1984(9) 0.0291(9) 0.0598(9) Uani 1 1 d .
C3 C 0.2563(10) 0.2032(9) 0.1391(8) 0.0598(9) Uani 1 1 d .
C4 C 0.3341(11) 0.0781(9) 0.1673(9) 0.0598(9) Uani 1 1 d .
C5 C 0.3031(10) -0.0610(8) 0.0585(8) 0.0598(9) Uani 1 1 d .
C6 C 0.2124(10) -0.0765(8) -0.0535(8) 0.0598(9) Uani 1 1 d .
C7 C 0.1029(11) 0.3487(9) -0.1081(9) 0.075(3) Uani 1 1 d .
H7A H 0.0523 0.4427 -0.1005 0.112 Uiso 1 1 calc R
H7B H 0.0240 0.2620 -0.1726 0.112 Uiso 1 1 calc R
H7C H 0.2294 0.3581 -0.1340 0.112 Uiso 1 1 calc R
C8 C 0.3811(11) 0.4754(8) 0.2319(8) 0.0819(13) Uani 1 1 d .
H8A H 0.4266 0.4750 0.1530 0.098 Uiso 1 1 calc R
C9 C 0.4063(12) 0.6084(9) 0.3408(8) 0.0819(13) Uani 1 1 d .
H9A H 0.4745 0.7003 0.3370 0.098 Uiso 1 1 calc R
C10 C 0.3366(11) 0.6071(9) 0.4479(8) 0.0819(13) Uani 1 1 d .
H10A H 0.3510 0.7004 0.5175 0.098 Uiso 1 1 calc R
C11 C 0.2436(12) 0.4769(8) 0.4644(8) 0.0819(13) Uani 1 1 d .
H11A H 0.2013 0.4776 0.5442 0.098 Uiso 1 1 calc R
C12 C 0.2158(12) 0.3458(9) 0.3582(8) 0.0819(13) Uani 1 1 d .
H12A H 0.1466 0.2548 0.3629 0.098 Uiso 1 1 calc R
C13 C 0.3791(11) -0.1883(9) 0.0727(9) 0.0598(9) Uani 1 1 d .
C14 C 0.1966(10) -0.2140(8) -0.1664(8) 0.0598(9) Uani 1 1 d .
N1 N 0.2859(10) 0.3456(7) 0.2475(7) 0.0819(13) Uani 1 1 d .
N2 N 0.4425(9) -0.2894(7) 0.0833(7) 0.075(3) Uani 1 1 d .
N3 N 0.1886(9) -0.3306(7) -0.2448(7) 0.089(3) Uani 1 1 d .
O1 O 0.0335(7) 0.0340(5) -0.1845(6) 0.0667(19) Uani 1 1 d .
O2 O 0.1075(7) 0.3240(6) 0.0146(6) 0.0665(18) Uani 1 1 d .
O3 O 0.4200(8) 0.0960(6) 0.2718(5) 0.076(2) 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 125.6(7)
O1 C1 C2 122.5(9)
C6 C1 C2 111.9(8)
C3 C2 O2 121.7(7)
C3 C2 C1 119.9(9)
O2 C2 C1 118.3(8)
C2 C3 N1 119.4(8)
C2 C3 C4 127.5(8)
N1 C3 C4 113.1(8)
O3 C4 C5 125.6(9)
O3 C4 C3 122.6(7)
C5 C4 C3 111.8(9)
C6 C5 C13 118.8(7)
C6 C5 C4 124.3(9)
C13 C5 C4 116.9(9)
C5 C6 C14 123.5(9)
C5 C6 C1 124.5(8)
C14 C6 C1 111.8(8)
O2 C7 H7A 109.5
O2 C7 H7B 109.5
H7A C7 H7B 109.5
O2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N1 C8 C9 115.6(8)
N1 C8 H8A 122.2
C9 C8 H8A 122.2
C10 C9 C8 121.0(9)
C10 C9 H9A 119.5
C8 C9 H9A 119.5
C9 C10 C11 123.5(8)
C9 C10 H10A 118.2
C11 C10 H10A 118.2
C12 C11 C10 116.2(9)
C12 C11 H11A 121.9
C10 C11 H11A 121.9
N1 C12 C11 120.8(9)
N1 C12 H12A 119.6
C11 C12 H12A 119.6
N2 C13 C5 178.9(10)
N3 C14 C6 171.9(10)
C12 N1 C8 122.8(7)
C12 N1 C3 118.6(8)
C8 N1 C3 118.6(7)
C2 O2 C7 121.1(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.259(9)
C1 C6 1.501(11)
C1 C2 1.525(9)
C2 C3 1.331(11)
C2 O2 1.369(9)
C3 N1 1.460(8)
C3 C4 1.482(12)
C4 O3 1.240(10)
C4 C5 1.442(9)
C5 C6 1.335(11)
C5 C13 1.430(11)
C6 C14 1.464(9)
C7 O2 1.453(9)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 N1 1.384(10)
C8 C9 1.410(9)
C8 H8A 0.9500
C9 C10 1.319(11)
C9 H9A 0.9500
C10 C11 1.385(10)
C10 H10A 0.9500
C11 C12 1.382(9)
C11 H11A 0.9500
C12 N1 1.353(11)
C12 H12A 0.9500
C13 N2 1.144(10)
C14 N3 1.147(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 C3 172.6(8)
C6 C1 C2 C3 -3.8(10)
O1 C1 C2 O2 -5.2(12)
C6 C1 C2 O2 178.4(7)
O2 C2 C3 N1 0.1(12)
C1 C2 C3 N1 -177.6(7)
O2 C2 C3 C4 -178.5(7)
C1 C2 C3 C4 3.8(13)
C2 C3 C4 O3 176.7(9)
N1 C3 C4 O3 -2.0(11)
C2 C3 C4 C5 -1.2(12)
N1 C3 C4 C5 -179.9(7)
O3 C4 C5 C6 -179.0(8)
C3 C4 C5 C6 -1.1(11)
O3 C4 C5 C13 -0.4(12)
C3 C4 C5 C13 177.4(7)
C13 C5 C6 C14 -4.2(12)
C4 C5 C6 C14 174.3(7)
C13 C5 C6 C1 -177.9(7)
C4 C5 C6 C1 0.7(12)
O1 C1 C6 C5 -174.5(8)
C2 C1 C6 C5 1.8(11)
O1 C1 C6 C14 11.2(11)
C2 C1 C6 C14 -172.6(6)
N1 C8 C9 C10 -2.2(13)
C8 C9 C10 C11 3.4(15)
C9 C10 C11 C12 -3.9(14)
C10 C11 C12 N1 3.6(14)
C6 C5 C13 N2 88(56)
C4 C5 C13 N2 -90(56)
C5 C6 C14 N3 22(6)
C1 C6 C14 N3 -164(6)
C11 C12 N1 C8 -2.8(14)
C11 C12 N1 C3 178.5(8)
C9 C8 N1 C12 2.0(13)
C9 C8 N1 C3 -179.4(7)
C2 C3 N1 C12 122.1(10)
C4 C3 N1 C12 -59.1(10)
C2 C3 N1 C8 -56.6(11)
C4 C3 N1 C8 122.2(8)
C3 C2 O2 C7 148.0(8)
C1 C2 O2 C7 -34.2(10)
