#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/30/2223043.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2223043
loop_
_publ_author_name
'Wang, Hai-Bo'
'Jing, Lin-Lin'
'Gao, Peng'
'Sun, Xiao-Li'
_publ_section_title
;
 4,4,5,5-Tetramethyl-2-(3,4,5-trimethoxyphenyl)imidazolidine-1-oxyl
 3-oxide
;
_journal_coeditor_code           DN2472
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2090
_journal_paper_doi               10.1107/S1600536809029274
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H23 N2 O5'
_chemical_formula_moiety         'C16 H23 N2 O5'
_chemical_formula_sum            'C16 H23 N2 O5'
_chemical_formula_weight         323.36
_chemical_name_systematic
;
4,4,5,5-Tetramethyl-2-(3,4,5-trimethoxyphenyl)imidazolidine-1-oxyl 3-oxide
;
_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                   20.623(3)
_cell_length_b                   7.2168(12)
_cell_length_c                   22.831(4)
_cell_measurement_reflns_used    1322
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.20
_cell_measurement_theta_min      3.12
_cell_volume                     3398.0(10)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       'φ and ω'
_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  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15858
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.227
_refine_ls_extinction_coef       0.0019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0462
_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)+(0.05P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                1519
_reflns_number_total             3027
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2472.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2223043
_cod_database_fobs_code          2223043
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.06793(9) 0.2073(3) 0.49665(8) 0.0570(5) Uani d . 1 . .
N N2 0.15280(9) 0.0432(3) 0.47376(8) 0.0576(5) Uani d . 1 . .
O O1 0.01712(9) 0.2652(3) 0.52296(7) 0.0913(6) Uani d . 1 . .
O O2 0.20243(8) -0.0630(3) 0.47707(7) 0.0903(6) Uani d . 1 . .
O O3 0.07153(8) 0.1394(2) 0.72841(6) 0.0717(5) Uani d . 1 . .
O O4 0.12645(7) -0.1894(2) 0.74689(6) 0.0720(5) Uani d . 1 . .
O O5 0.17240(8) -0.3947(2) 0.65885(7) 0.0743(5) Uani d . 1 . .
C C1 0.08745(10) 0.2830(3) 0.43780(9) 0.0511(6) Uani d . 1 . .
C C2 0.13132(10) 0.1227(3) 0.41649(9) 0.0548(6) Uani d . 1 . .
C C3 0.11082(10) 0.0839(3) 0.51744(9) 0.0506(6) Uani d . 1 . .
C C4 0.11306(10) 0.0103(3) 0.57690(9) 0.0505(6) Uani d . 1 . .
C C5 0.14140(10) -0.1615(3) 0.58697(10) 0.0533(6) Uani d . 1 . .
H H5 0.1574 -0.2313 0.5559 0.064 Uiso calc R 1 . .
C C6 0.14551(10) -0.2276(3) 0.64375(10) 0.0550(6) Uani d . 1 . .
C C7 0.12210(10) -0.1231(3) 0.69035(10) 0.0542(6) Uani d . 1 . .
C C8 0.09320(11) 0.0479(3) 0.67984(9) 0.0543(6) Uani d . 1 . .
C C9 0.08840(10) 0.1132(3) 0.62324(9) 0.0539(6) Uani d . 1 . .
H H9 0.0686 0.2266 0.6161 0.065 Uiso calc R 1 . .
C C10 0.03918(13) 0.3130(4) 0.71996(10) 0.0823(8) Uani d . 1 . .
H H10A 0.0693 0.4022 0.7047 0.123 Uiso calc R 1 . .
H H10B 0.0224 0.3562 0.7567 0.123 Uiso calc R 1 . .
H H10C 0.0041 0.2971 0.6928 0.123 Uiso calc R 1 . .
C C11 0.18747(13) -0.1598(5) 0.77318(11) 0.1017(10) Uani d . 1 . .
H H11A 0.2203 -0.2234 0.7511 0.153 Uiso calc R 1 . .
H H11B 0.1868 -0.2064 0.8126 0.153 Uiso calc R 1 . .
H H11C 0.1968 -0.0295 0.7737 0.153 Uiso calc R 1 . .
C C12 0.19952(13) -0.5035(4) 0.61337(12) 0.0869(8) Uani d . 1 . .
H H12A 0.1663 -0.5354 0.5857 0.130 Uiso calc R 1 . .
H H12B 0.2177 -0.6146 0.6296 0.130 Uiso calc R 1 . .
H H12C 0.2329 -0.4343 0.5940 0.130 Uiso calc R 1 . .
C C13 0.12386(12) 0.4629(3) 0.45043(11) 0.0726(7) Uani d . 1 . .
H H13A 0.0965 0.5449 0.4724 0.109 Uiso calc R 1 . .
H H13B 0.1358 0.5209 0.4141 0.109 Uiso calc R 1 . .
H H13C 0.1622 0.4360 0.4727 0.109 Uiso calc R 1 . .
C C14 0.02814(11) 0.3224(3) 0.40075(10) 0.0722(7) Uani d . 1 . .
H H14A 0.0019 0.2129 0.3984 0.108 Uiso calc R 1 . .
H H14B 0.0414 0.3586 0.3621 0.108 Uiso calc R 1 . .
H H14C 0.0035 0.4207 0.4183 0.108 Uiso calc R 1 . .
C C15 0.18983(12) 0.1816(4) 0.38065(10) 0.0783(8) Uani d . 1 . .
H H15A 0.2168 0.2619 0.4037 0.117 Uiso calc R 1 . .
H H15B 0.1756 0.2462 0.3462 0.117 Uiso calc R 1 . .
H H15C 0.2141 0.0739 0.3694 0.117 Uiso calc R 1 . .
C C16 0.09402(13) -0.0316(3) 0.38572(10) 0.0765(8) Uani d . 1 . .
H H16A 0.1214 -0.1385 0.3818 0.115 Uiso calc R 1 . .
H H16B 0.0808 0.0099 0.3476 0.115 Uiso calc R 1 . .
H H16C 0.0564 -0.0633 0.4084 0.115 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 N1 C3 . . 126.26(18) ?
O1 N1 C1 . . 121.31(18) ?
C3 N1 C1 . . 112.36(17) ?
O2 N2 C3 . . 126.70(19) ?
O2 N2 C2 . . 121.20(17) ?
C3 N2 C2 . . 111.83(17) ?
C8 O3 C10 . . 117.76(17) ?
C7 O4 C11 . . 113.82(18) ?
C6 O5 C12 . . 117.56(18) ?
N1 C1 C14 . . 110.53(17) ?
N1 C1 C13 . . 105.77(17) ?
C14 C1 C13 . . 110.08(19) ?
N1 C1 C2 . . 99.52(16) ?
C14 C1 C2 . . 115.92(18) ?
C13 C1 C2 . . 114.05(18) ?
N2 C2 C15 . . 110.07(18) ?
N2 C2 C16 . . 105.78(18) ?
C15 C2 C16 . . 110.91(19) ?
N2 C2 C1 . . 100.67(16) ?
C15 C2 C1 . . 115.15(19) ?
C16 C2 C1 . . 113.33(18) ?
N1 C3 N2 . . 107.77(18) ?
N1 C3 C4 . . 126.3(2) ?
N2 C3 C4 . . 125.9(2) ?
C9 C4 C5 . . 120.32(19) ?
C9 C4 C3 . . 120.2(2) ?
C5 C4 C3 . . 119.5(2) ?
C6 C5 C4 . . 119.2(2) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
O5 C6 C5 . . 124.3(2) ?
O5 C6 C7 . . 115.1(2) ?
C5 C6 C7 . . 120.6(2) ?
O4 C7 C6 . . 120.4(2) ?
O4 C7 C8 . . 119.8(2) ?
C6 C7 C8 . . 119.9(2) ?
O3 C8 C9 . . 124.9(2) ?
O3 C8 C7 . . 115.40(19) ?
C9 C8 C7 . . 119.7(2) ?
C8 C9 C4 . . 120.3(2) ?
C8 C9 H9 . . 119.8 ?
C4 C9 H9 . . 119.8 ?
O3 C10 H10A . . 109.5 ?
O3 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
O3 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O4 C11 H11A . . 109.5 ?
O4 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O4 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O5 C12 H12A . . 109.5 ?
O5 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
O5 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C1 C13 H13A . . 109.5 ?
C1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C1 C14 H14A . . 109.5 ?
C1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C2 C15 H15A . . 109.5 ?
C2 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C2 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C2 C16 H16A . . 109.5 ?
C2 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C2 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 O1 . 1.278(2) ?
N1 C3 . 1.342(2) ?
N1 C1 . 1.506(3) ?
N2 O2 . 1.281(2) ?
N2 C3 . 1.353(2) ?
N2 C2 . 1.495(3) ?
O3 C8 . 1.366(2) ?
O3 C10 . 1.433(3) ?
O4 C7 . 1.380(2) ?
O4 C11 . 1.410(3) ?
O5 C6 . 1.372(3) ?
O5 C12 . 1.417(3) ?
C1 C14 . 1.514(3) ?
C1 C13 . 1.527(3) ?
C1 C2 . 1.547(3) ?
C2 C15 . 1.519(3) ?
C2 C16 . 1.525(3) ?
C3 C4 . 1.459(3) ?
C4 C9 . 1.389(3) ?
C4 C5 . 1.390(3) ?
C5 C6 . 1.384(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.391(3) ?
C7 C8 . 1.391(3) ?
C8 C9 . 1.379(3) ?
C9 H9 . 0.9300 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C14 H14A Cg2 5_556 0.96 2.80 3.644(2) 147
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 N1 C1 C14 . . . . -36.5(3) ?
C3 N1 C1 C14 . . . . 146.39(19) ?
O1 N1 C1 C13 . . . . 82.7(2) ?
C3 N1 C1 C13 . . . . -94.5(2) ?
O1 N1 C1 C2 . . . . -158.87(19) ?
C3 N1 C1 C2 . . . . 24.0(2) ?
O2 N2 C2 C15 . . . . -40.2(3) ?
C3 N2 C2 C15 . . . . 145.36(19) ?
O2 N2 C2 C16 . . . . 79.7(2) ?
C3 N2 C2 C16 . . . . -94.8(2) ?
O2 N2 C2 C1 . . . . -162.2(2) ?
C3 N2 C2 C1 . . . . 23.4(2) ?
N1 C1 C2 N2 . . . . -25.95(19) ?
C14 C1 C2 N2 . . . . -144.43(19) ?
C13 C1 C2 N2 . . . . 86.2(2) ?
N1 C1 C2 C15 . . . . -144.27(19) ?
C14 C1 C2 C15 . . . . 97.3(2) ?
C13 C1 C2 C15 . . . . -32.1(3) ?
N1 C1 C2 C16 . . . . 86.5(2) ?
C14 C1 C2 C16 . . . . -31.9(3) ?
C13 C1 C2 C16 . . . . -161.33(18) ?
O1 N1 C3 N2 . . . . 172.6(2) ?
C1 N1 C3 N2 . . . . -10.4(2) ?
O1 N1 C3 C4 . . . . -8.9(4) ?
C1 N1 C3 C4 . . . . 168.07(19) ?
O2 N2 C3 N1 . . . . 176.8(2) ?
C2 N2 C3 N1 . . . . -9.1(2) ?
O2 N2 C3 C4 . . . . -1.7(4) ?
C2 N2 C3 C4 . . . . 172.4(2) ?
N1 C3 C4 C9 . . . . -26.4(3) ?
N2 C3 C4 C9 . . . . 151.8(2) ?
N1 C3 C4 C5 . . . . 155.1(2) ?
N2 C3 C4 C5 . . . . -26.7(3) ?
C9 C4 C5 C6 . . . . -0.9(3) ?
C3 C4 C5 C6 . . . . 177.65(19) ?
C12 O5 C6 C5 . . . . 2.1(3) ?
C12 O5 C6 C7 . . . . -177.4(2) ?
C4 C5 C6 O5 . . . . -179.98(19) ?
C4 C5 C6 C7 . . . . -0.5(3) ?
C11 O4 C7 C6 . . . . 82.3(3) ?
C11 O4 C7 C8 . . . . -98.7(3) ?
O5 C6 C7 O4 . . . . -0.3(3) ?
C5 C6 C7 O4 . . . . -179.84(19) ?
O5 C6 C7 C8 . . . . -179.30(19) ?
C5 C6 C7 C8 . . . . 1.2(3) ?
C10 O3 C8 C9 . . . . 2.5(3) ?
C10 O3 C8 C7 . . . . -177.7(2) ?
O4 C7 C8 O3 . . . . 0.7(3) ?
C6 C7 C8 O3 . . . . 179.72(19) ?
O4 C7 C8 C9 . . . . -179.5(2) ?
C6 C7 C8 C9 . . . . -0.5(3) ?
O3 C8 C9 C4 . . . . 178.9(2) ?
C7 C8 C9 C4 . . . . -0.9(3) ?
C5 C4 C9 C8 . . . . 1.6(3) ?
C3 C4 C9 C8 . . . . -176.9(2) ?
