#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024456.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_4024456
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            'C22 H28 N6 O6'
_chemical_formula_weight         472.50
_chemical_name_systematic
; 
 2,3-Bis(4,4,5,5-tetramethyl-3-oxid-1-oxyl-4,5
 -dihydro-1H-imidazol-2-yl)quinoxaline 1,4-dioxide
;
_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                 95.388(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3405(9)
_cell_length_b                   17.496(2)
_cell_length_c                   17.596(2)
_cell_measurement_reflns_used    3504
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.45
_cell_measurement_theta_min      2.33
_cell_volume                     2249.8(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0833
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22257
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0003(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   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         4595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0549
_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)+(0.0603P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                3055
_reflns_number_total             4595
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900085s_si_010.cif
_cod_data_source_block           881a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P2(1)/c
_cod_database_code               4024456
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1477(2) 0.01484(9) 0.28108(9) 0.0502(5) Uani 1 1 d . . .
N1 N 0.2651(2) 0.06856(10) 0.28614(9) 0.0335(4) Uani 1 1 d . . .
C1 C 0.3253(3) 0.10692(12) 0.36100(11) 0.0305(5) Uani 1 1 d . . .
C2 C 0.3826(4) 0.04671(17) 0.42049(15) 0.0459(6) Uani 1 1 d . . .
H27A H 0.271(4) 0.0178(16) 0.4343(16) 0.068(8) Uiso 1 1 d . . .
H27B H 0.427(4) 0.0715(16) 0.4654(16) 0.064(9) Uiso 1 1 d . . .
H27C H 0.471(4) 0.0122(16) 0.4032(15) 0.064(8) Uiso 1 1 d . . .
C3 C 0.1605(4) 0.15070(17) 0.38271(16) 0.0427(6) Uani 1 1 d . . .
H25A H 0.061(4) 0.1132(16) 0.3921(15) 0.069(8) Uiso 1 1 d . . .
H25B H 0.118(3) 0.1891(14) 0.3447(14) 0.051(7) Uiso 1 1 d . . .
H25C H 0.190(3) 0.1751(13) 0.4320(15) 0.044(6) Uiso 1 1 d . . .
C4 C 0.4841(3) 0.15797(13) 0.33806(12) 0.0381(6) Uani 1 1 d . . .
C5 C 0.6706(4) 0.1189(2) 0.3460(2) 0.0666(10) Uani 1 1 d . . .
H2A H 0.752(5) 0.1459(19) 0.3208(19) 0.092(11) Uiso 1 1 d . . .
H2B H 0.658(4) 0.0637(18) 0.3217(16) 0.069(10) Uiso 1 1 d . . .
H2C H 0.718(4) 0.1144(16) 0.3986(18) 0.070(9) Uiso 1 1 d . . .
C6 C 0.4927(6) 0.2364(2) 0.37418(19) 0.0651(10) Uani 1 1 d . . .
H32A H 0.572(4) 0.2632(17) 0.3525(16) 0.068(9) Uiso 1 1 d . . .
H32B H 0.516(4) 0.2300(16) 0.4250(19) 0.071(9) Uiso 1 1 d . . .
H32C H 0.376(6) 0.269(3) 0.362(2) 0.137(18) Uiso 1 1 d . . .
N2 N 0.4365(2) 0.16408(10) 0.25330(10) 0.0322(4) Uani 1 1 d . . .
O2 O 0.5138(2) 0.21104(10) 0.21161(9) 0.0493(5) Uani 1 1 d . . .
C7 C 0.3274(3) 0.10643(12) 0.22762(11) 0.0299(5) Uani 1 1 d . . .
C8 C 0.2831(3) 0.08903(12) 0.14683(11) 0.0300(5) Uani 1 1 d . . .
C9 C 0.2116(3) 0.14503(12) 0.09518(11) 0.0298(5) Uani 1 1 d . . .
C10 C 0.1580(3) 0.22047(12) 0.12093(11) 0.0292(5) Uani 1 1 d . . .
O3 O -0.0480(2) 0.17718(8) 0.20411(9) 0.0429(4) Uani 1 1 d . . .
N3 N 0.0301(2) 0.23029(9) 0.16985(10) 0.0317(4) Uani 1 1 d . . .
C11 C -0.0273(3) 0.31254(12) 0.17230(13) 0.0354(5) Uani 1 1 d . . .
C12 C -0.0691(6) 0.33264(17) 0.25269(18) 0.0571(8) Uani 1 1 d . . .
H31A H 0.033(4) 0.3226(18) 0.2914(18) 0.083(12) Uiso 1 1 d . . .
H31B H -0.170(4) 0.3016(16) 0.2650(15) 0.067(9) Uiso 1 1 d . . .
H31C H -0.101(3) 0.3873(16) 0.2550(14) 0.053(7) Uiso 1 1 d . . .
C13 C -0.2000(4) 0.31793(18) 0.1169(2) 0.0557(8) Uani 1 1 d . . .
H29A H -0.175(3) 0.3071(15) 0.0628(16) 0.057(8) Uiso 1 1 d . . .
H29B H -0.248(4) 0.3677(18) 0.1172(16) 0.070(9) Uiso 1 1 d . . .
H29C H -0.295(4) 0.2822(15) 0.1329(14) 0.059(8) Uiso 1 1 d . . .
C14 C 0.1414(3) 0.35291(12) 0.14308(12) 0.0342(5) Uani 1 1 d . . .
C15 C 0.2870(4) 0.37619(18) 0.20589(17) 0.0523(7) Uani 1 1 d . . .
H33A H 0.397(4) 0.3908(17) 0.1829(16) 0.077(10) Uiso 1 1 d . . .
H33B H 0.319(3) 0.3341(15) 0.2434(15) 0.054(7) Uiso 1 1 d . . .
H33C H 0.238(4) 0.4245(18) 0.2324(16) 0.080(9) Uiso 1 1 d . . .
C16 C 0.0968(4) 0.41976(15) 0.08961(16) 0.0451(6) Uani 1 1 d . . .
H24A H 0.018(3) 0.4030(13) 0.0426(14) 0.046(7) Uiso 1 1 d . . .
H24B H 0.211(4) 0.4367(15) 0.0739(15) 0.063(8) Uiso 1 1 d . . .
H24C H 0.042(4) 0.4587(16) 0.1150(15) 0.060(8) Uiso 1 1 d . . .
O4 O 0.3498(2) 0.29858(9) 0.05683(8) 0.0421(4) Uani 1 1 d . . .
N4 N 0.2221(2) 0.28829(10) 0.09995(9) 0.0312(4) Uani 1 1 d . . .
O5 O 0.1028(2) 0.17930(9) -0.02676(9) 0.0506(5) Uani 1 1 d . . .
N5 N 0.1755(2) 0.12926(10) 0.02060(10) 0.0339(4) Uani 1 1 d . . .
C17 C 0.2110(3) 0.05557(13) -0.00559(12) 0.0342(5) Uani 1 1 d . . .
C18 C 0.1723(4) 0.03713(16) -0.08257(14) 0.0467(7) Uani 1 1 d . . .
H23A H 0.118(4) 0.0710(17) -0.1142(16) 0.064(9) Uiso 1 1 d . . .
C19 C 0.2066(4) -0.03491(16) -0.10713(16) 0.0537(7) Uani 1 1 d . . .
H20A H 0.178(3) -0.0440(15) -0.1582(15) 0.061(8) Uiso 1 1 d . . .
C20 C 0.2780(4) -0.09028(16) -0.05622(16) 0.0533(7) Uani 1 1 d . . .
H30A H 0.304(3) -0.1412(15) -0.0720(14) 0.056(8) Uiso 1 1 d . . .
C21 C 0.3151(4) -0.07400(14) 0.01955(16) 0.0463(6) Uani 1 1 d . . .
H22A H 0.362(3) -0.1091(14) 0.0558(14) 0.047(7) Uiso 1 1 d . . .
C22 C 0.2813(3) -0.00041(12) 0.04578(12) 0.0345(5) Uani 1 1 d . . .
N6 N 0.3213(2) 0.01746(10) 0.12349(10) 0.0347(4) Uani 1 1 d . . .
O6 O 0.3963(2) -0.03218(9) 0.16960(9) 0.0516(5) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C7 126.08(18) . . ?
O1 N1 C1 122.08(16) . . ?
C7 N1 C1 110.99(17) . . ?
N1 C1 C3 105.71(18) . . ?
N1 C1 C2 109.49(19) . . ?
C3 C1 C2 110.8(2) . . ?
N1 C1 C4 101.23(15) . . ?
C3 C1 C4 114.4(2) . . ?
C2 C1 C4 114.4(2) . . ?
N2 C4 C6 110.4(2) . . ?
N2 C4 C5 104.2(2) . . ?
C6 C4 C5 111.5(3) . . ?
N2 C4 C1 100.87(16) . . ?
C6 C4 C1 114.6(2) . . ?
C5 C4 C1 114.1(2) . . ?
O2 N2 C7 125.28(17) . . ?
O2 N2 C4 122.97(17) . . ?
C7 N2 C4 110.91(16) . . ?
N2 C7 N1 110.45(18) . . ?
N2 C7 C8 123.81(17) . . ?
N1 C7 C8 125.74(19) . . ?
N6 C8 C9 121.59(18) . . ?
N6 C8 C7 117.01(18) . . ?
C9 C8 C7 121.35(18) . . ?
N5 C9 C8 121.11(19) . . ?
N5 C9 C10 117.03(18) . . ?
C8 C9 C10 121.64(18) . . ?
N4 C10 N3 110.35(17) . . ?
N4 C10 C9 127.03(17) . . ?
N3 C10 C9 122.61(17) . . ?
O3 N3 C10 125.67(17) . . ?
O3 N3 C11 123.09(16) . . ?
C10 N3 C11 110.86(16) . . ?
N3 C11 C12 109.32(19) . . ?
N3 C11 C13 105.0(2) . . ?
C12 C11 C13 110.7(2) . . ?
N3 C11 C14 101.04(16) . . ?
C12 C11 C14 116.1(2) . . ?
C13 C11 C14 113.6(2) . . ?
N4 C14 C16 109.67(18) . . ?
N4 C14 C15 106.45(19) . . ?
C16 C14 C15 109.9(2) . . ?
N4 C14 C11 100.84(16) . . ?
C16 C14 C11 115.0(2) . . ?
C15 C14 C11 114.2(2) . . ?
O4 N4 C10 125.89(17) . . ?
O4 N4 C14 122.58(16) . . ?
C10 N4 C14 111.04(15) . . ?
O5 N5 C9 121.58(18) . . ?
O5 N5 C17 119.37(17) . . ?
C9 N5 C17 118.99(18) . . ?
C18 C17 C22 119.6(2) . . ?
C18 C17 N5 120.3(2) . . ?
C22 C17 N5 120.03(19) . . ?
C19 C18 C17 119.6(3) . . ?
C18 C19 C20 120.7(3) . . ?
C21 C20 C19 120.9(3) . . ?
C20 C21 C22 119.3(3) . . ?
C21 C22 C17 119.9(2) . . ?
C21 C22 N6 119.9(2) . . ?
C17 C22 N6 120.22(19) . . ?
O6 N6 C8 121.66(18) . . ?
O6 N6 C22 120.29(18) . . ?
C8 N6 C22 118.02(18) . . ?
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
O1 N1 1.273(2) . ?
N1 C7 1.340(2) . ?
N1 C1 1.507(3) . ?
C1 C3 1.511(3) . ?
C1 C2 1.517(3) . ?
C1 C4 1.552(3) . ?
C4 N2 1.503(3) . ?
C4 C6 1.512(4) . ?
C4 C5 1.524(4) . ?
N2 O2 1.270(2) . ?
N2 C7 1.340(3) . ?
C7 C8 1.460(3) . ?
C8 N6 1.355(3) . ?
C8 C9 1.404(3) . ?
C9 N5 1.343(3) . ?
C9 C10 1.461(3) . ?
C10 N4 1.341(3) . ?
C10 N3 1.343(2) . ?
O3 N3 1.273(2) . ?
N3 C11 1.501(3) . ?
C11 C12 1.517(3) . ?
C11 C13 1.528(4) . ?
C11 C14 1.554(3) . ?
C14 N4 1.513(3) . ?
C14 C16 1.517(3) . ?
C14 C15 1.519(3) . ?
O4 N4 1.273(2) . ?
O5 N5 1.289(2) . ?
N5 C17 1.402(3) . ?
C17 C18 1.395(3) . ?
C17 C22 1.398(3) . ?
C18 C19 1.363(4) . ?
C19 C20 1.388(4) . ?
C20 C21 1.366(4) . ?
C21 C22 1.398(3) . ?
C22 N6 1.407(3) . ?
N6 O6 1.277(2) . ?
