#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024451.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_4024451
loop_
_publ_author_name
'Oleg N. Chupakhin'
'Irina A. Utepova'
'Mikhail V. Varaksin'
'Evgeny V. Tretyakov'
'Galina V. Romanenko'
'Dmitry V. Stass'
'Victor I. Ovcharenko'
_publ_section_title
;
SNH Approach in the Synthesis of Nitronyl Nitroxides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2870
_journal_page_last               2872
_journal_paper_doi               10.1021/jo900085s
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C11 H15 N4 O3'
_chemical_formula_weight         251.27
_chemical_name_systematic
; 
 4,4,5,5-Tetramethyl-2-(6-(pyridin-2-yl)-1-oxidopyridin-2-yl)-
 4,5-dihydro-1H-imidazole 3-Oxide 1-Oxyl  
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.644(2)
_cell_length_b                   14.876(3)
_cell_length_c                   15.388(3)
_cell_measurement_temperature    293(2)
_cell_volume                     2436.7(8)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.1188
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20629
_diffrn_reflns_theta_full        26.52
_diffrn_reflns_theta_max         26.52
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0668
_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)+(0.1304P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1989
_refine_ls_wR_factor_ref         0.2185
_reflns_number_gt                1566
_reflns_number_total             2491
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900085s_si_005.cif
_cod_data_source_block           zzzs
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4024451
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
N1 N 0.3019(2) -0.01759(15) 0.75751(14) 0.0581(7) Uani 1 1 d . . .
O1 O 0.3413(3) -0.05049(16) 0.82825(14) 0.1033(10) Uani 1 1 d . . .
C1 C 0.2912(2) -0.07270(18) 0.67672(17) 0.0515(7) Uani 1 1 d . . .
N2 N 0.2296(2) 0.07972(13) 0.66463(13) 0.0462(6) Uani 1 1 d . . .
O2 O 0.1844(3) 0.15249(13) 0.63402(14) 0.0811(8) Uani 1 1 d . . .
C2 C 0.1917(4) -0.1443(3) 0.6938(3) 0.0877(12) Uani 1 1 d . . .
H2A H 0.2225 -0.1862 0.7363 0.123(16) Uiso 1 1 calc R . .
H2B H 0.1735 -0.1757 0.6407 0.104(13) Uiso 1 1 calc R . .
H2C H 0.1165 -0.1163 0.7150 0.138(18) Uiso 1 1 calc R . .
N3 N 0.1283(2) 0.15646(15) 0.83753(15) 0.0544(6) Uani 1 1 d . . .
O3 O 0.03344(18) 0.12178(18) 0.79887(15) 0.0826(8) Uani 1 1 d . . .
C3 C 0.4149(3) -0.1176(3) 0.6588(3) 0.0844(11) Uani 1 1 d . . .
H3A H 0.4325 -0.1604 0.7038 0.117(15) Uiso 1 1 calc R . .
H3B H 0.4802 -0.0731 0.6573 0.068(9) Uiso 1 1 calc R . .
H3C H 0.4110 -0.1478 0.6037 0.136(17) Uiso 1 1 calc R . .
N4 N 0.3343(3) 0.22620(17) 0.92612(16) 0.0702(7) Uani 1 1 d . . .
C4 C 0.2498(2) -0.00120(17) 0.60856(16) 0.0479(7) Uani 1 1 d . . .
C5 C 0.3511(4) 0.0227(3) 0.5431(3) 0.0932(13) Uani 1 1 d . . .
H5A H 0.3194 0.0669 0.5033 0.138(17) Uiso 1 1 calc R . .
H5B H 0.3751 -0.0302 0.5115 0.140(18) Uiso 1 1 calc R . .
H5C H 0.4229 0.0464 0.5730 0.135(19) Uiso 1 1 calc R . .
C6 C 0.1283(3) -0.0198(3) 0.5615(3) 0.0876(12) Uani 1 1 d . . .
H6A H 0.1115 0.0281 0.5213 0.16(2) Uiso 1 1 calc R . .
H6B H 0.0610 -0.0237 0.6028 0.067(9) Uiso 1 1 calc R . .
H6C H 0.1350 -0.0755 0.5304 0.118(15) Uiso 1 1 calc R . .
C7 C 0.2600(2) 0.06597(16) 0.74669(15) 0.0402(6) Uani 1 1 d . . .
C8 C 0.2476(2) 0.13237(15) 0.81595(14) 0.0413(6) Uani 1 1 d . . .
C9 C 0.1134(3) 0.2172(2) 0.9025(2) 0.0671(8) Uani 1 1 d . . .
H9A H 0.0335 0.2362 0.9185 0.091(11) Uiso 1 1 calc R . .
C10 C 0.2165(4) 0.2499(2) 0.94416(19) 0.0680(9) Uani 1 1 d . . .
H10A H 0.2038 0.2917 0.9883 0.067(8) Uiso 1 1 calc R . .
C11 C 0.3465(3) 0.16824(17) 0.86154(18) 0.0541(7) Uani 1 1 d . . .
H11A H 0.4272 0.1506 0.8460 0.080(10) 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
O1 N1 C7 125.5(2) . . ?
O1 N1 C1 122.0(2) . . ?
C7 N1 C1 112.50(19) . . ?
N1 C1 C3 109.3(2) . . ?
N1 C1 C2 107.1(3) . . ?
C3 C1 C2 109.3(3) . . ?
N1 C1 C4 102.0(2) . . ?
C3 C1 C4 115.3(3) . . ?
C2 C1 C4 113.4(3) . . ?
O2 N2 C7 125.3(2) . . ?
O2 N2 C4 121.6(2) . . ?
C7 N2 C4 113.1(2) . . ?
O3 N3 C9 121.2(2) . . ?
O3 N3 C8 121.1(2) . . ?
C9 N3 C8 117.7(2) . . ?
C11 N4 C10 114.9(3) . . ?
N2 C4 C6 107.5(2) . . ?
N2 C4 C5 107.2(3) . . ?
C6 C4 C5 109.5(3) . . ?
N2 C4 C1 101.6(2) . . ?
C6 C4 C1 116.1(3) . . ?
C5 C4 C1 114.0(2) . . ?
N2 C7 N1 110.3(2) . . ?
N2 C7 C8 124.9(2) . . ?
N1 C7 C8 124.8(2) . . ?
N3 C8 C11 119.2(2) . . ?
N3 C8 C7 116.1(2) . . ?
C11 C8 C7 124.6(2) . . ?
N3 C9 C10 119.4(3) . . ?
N4 C10 C9 124.5(3) . . ?
N4 C11 C8 124.3(3) . . ?
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 O1 1.265(3) . ?
N1 C7 1.331(3) . ?
N1 C1 1.494(3) . ?
C1 C3 1.502(4) . ?
C1 C2 1.525(4) . ?
C1 C4 1.557(4) . ?
N2 O2 1.275(3) . ?
N2 C7 1.319(3) . ?
N2 C4 1.497(3) . ?
N3 O3 1.280(3) . ?
N3 C9 1.357(4) . ?
N3 C8 1.361(3) . ?
N4 C11 1.322(4) . ?
N4 C10 1.332(4) . ?
C4 C6 1.508(4) . ?
C4 C5 1.518(4) . ?
C7 C8 1.459(3) . ?
C8 C11 1.373(4) . ?
C9 C10 1.361(4) . ?
