#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/49/2224957.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_2224957
loop_
_publ_author_name
'Wang, Hai-Bo'
'Jing, Lin-Lin'
'Jiang, Ru'
'Liu, Peng'
'Sun, Xiao-Li'
_publ_section_title
;
 2-(1H-Indol-3-yl)-4,4,5,5-tetramethylimidazolidine-1-oxyl
 3-oxide
;
_journal_coeditor_code           FL2283
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o428
_journal_paper_doi               10.1107/S1600536810002175
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H18 N3 O2'
_chemical_formula_moiety         'C15 H18 N3 O2'
_chemical_formula_sum            'C15 H18 N3 O2'
_chemical_formula_weight         272.32
_chemical_name_systematic
;
2-(1H-Indol-3-yl)-4,4,5,5-tetramethylimidazolidine-1-oxyl 3-oxide
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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            4
_cell_length_a                   15.0810(15)
_cell_length_b                   8.7700(8)
_cell_length_c                   10.6108(10)
_cell_measurement_reflns_used    2598
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.38
_cell_measurement_theta_min      2.69
_cell_volume                     1403.4(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6651
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.088
_refine_ls_extinction_coef       0.0146(19)
_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   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1323
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0250
_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)+(0.0394P)²+0.1053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0668
_reflns_number_gt                1208
_reflns_number_total             1323
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fl2283.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               2224957
_cod_database_fobs_code          2224957
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
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 -0.01319(14) 1.0261(2) 0.9413(2) 0.0605(5) Uani d . 1 . .
H H1 -0.0087 1.0928 1.0004 0.073 Uiso calc R 1 . .
N N2 0.11909(10) 0.60749(18) 0.83997(15) 0.0393(4) Uani d . 1 . .
N N3 0.05128(10) 0.62465(17) 0.65920(15) 0.0381(4) Uani d . 1 . .
O O1 0.14925(11) 0.64081(18) 0.94892(14) 0.0579(4) Uani d . 1 . .
O O2 0.01465(11) 0.68277(17) 0.56075(14) 0.0545(4) Uani d . 1 . .
C C1 -0.08282(15) 1.0156(2) 0.8579(2) 0.0534(6) Uani d . 1 . .
C C2 -0.16017(18) 1.1028(3) 0.8506(3) 0.0731(8) Uani d . 1 . .
H H2 -0.1707 1.1825 0.9064 0.088 Uiso calc R 1 . .
C C3 -0.21965(16) 1.0666(3) 0.7587(4) 0.0795(9) Uani d . 1 . .
H H3 -0.2715 1.1234 0.7516 0.095 Uiso calc R 1 . .
C C4 -0.20480(15) 0.9465(3) 0.6750(3) 0.0692(7) Uani d . 1 . .
H H4 -0.2463 0.9255 0.6126 0.083 Uiso calc R 1 . .
C C5 -0.12892(14) 0.8583(2) 0.6839(2) 0.0529(6) Uani d . 1 . .
H H5 -0.1201 0.7769 0.6292 0.063 Uiso calc R 1 . .
C C6 -0.06560(13) 0.8930(2) 0.7760(2) 0.0442(5) Uani d . 1 . .
C C7 0.01895(13) 0.8304(2) 0.81520(18) 0.0407(5) Uani d . 1 . .
C C8 0.04679(15) 0.9165(2) 0.9167(2) 0.0515(5) Uani d . 1 . .
H H8 0.0991 0.9010 0.9614 0.062 Uiso calc R 1 . .
C C9 0.06218(12) 0.6932(2) 0.77161(18) 0.0363(4) Uani d . 1 . .
C C10 0.15347(12) 0.4734(2) 0.76668(19) 0.0385(4) Uani d . 1 . .
C C11 0.24518(16) 0.5183(2) 0.7176(2) 0.0523(5) Uani d . 1 . .
H H11A 0.2395 0.6018 0.6597 0.079 Uiso calc R 1 . .
H H11B 0.2715 0.4328 0.6752 0.079 Uiso calc R 1 . .
H H11C 0.2821 0.5483 0.7870 0.079 Uiso calc R 1 . .
C C12 0.15962(15) 0.3356(2) 0.8531(2) 0.0516(5) Uani d . 1 . .
H H12A 0.2043 0.3532 0.9158 0.077 Uiso calc R 1 . .
H H12B 0.1749 0.2471 0.8045 0.077 Uiso calc R 1 . .
H H12C 0.1035 0.3195 0.8936 0.077 Uiso calc R 1 . .
C C13 0.08199(13) 0.4624(2) 0.66190(19) 0.0381(4) Uani d . 1 . .
C C14 0.00154(14) 0.3668(2) 0.6989(2) 0.0516(5) Uani d . 1 . .
H H14A -0.0183 0.3965 0.7813 0.077 Uiso calc R 1 . .
H H14B 0.0176 0.2609 0.6997 0.077 Uiso calc R 1 . .
H H14C -0.0453 0.3829 0.6391 0.077 Uiso calc R 1 . .
C C15 0.11578(16) 0.4160(3) 0.5331(2) 0.0556(6) Uani d . 1 . .
H H15A 0.0674 0.4150 0.4743 0.083 Uiso calc R 1 . .
H H15B 0.1415 0.3161 0.5379 0.083 Uiso calc R 1 . .
H H15C 0.1598 0.4876 0.5054 0.083 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
C8 N1 C1 . . 109.91(19) ?
C8 N1 H1 . . 125.0 ?
C1 N1 H1 . . 125.0 ?
O1 N2 C9 . . 125.79(16) ?
O1 N2 C10 . . 121.68(16) ?
C9 N2 C10 . . 112.14(16) ?
O2 N3 C9 . . 126.49(15) ?
O2 N3 C13 . . 121.66(15) ?
C9 N3 C13 . . 111.73(15) ?
N1 C1 C2 . . 129.5(2) ?
N1 C1 C6 . . 107.89(19) ?
C2 C1 C6 . . 122.6(3) ?
C3 C2 C1 . . 117.5(3) ?
C3 C2 H2 . . 121.2 ?
C1 C2 H2 . . 121.2 ?
C2 C3 C4 . . 121.7(2) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C5 C4 C3 . . 120.7(3) ?
C5 C4 H4 . . 119.6 ?
C3 C4 H4 . . 119.6 ?
C4 C5 C6 . . 119.3(2) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C5 C6 C1 . . 118.12(19) ?
C5 C6 C7 . . 135.90(19) ?
C1 C6 C7 . . 105.97(19) ?
C8 C7 C9 . . 124.61(19) ?
C8 C7 C6 . . 106.51(17) ?
C9 C7 C6 . . 128.38(18) ?
N1 C8 C7 . . 109.7(2) ?
N1 C8 H8 . . 125.1 ?
C7 C8 H8 . . 125.1 ?
N3 C9 N2 . . 107.72(15) ?
N3 C9 C7 . . 126.94(17) ?
N2 C9 C7 . . 125.30(17) ?
N2 C10 C12 . . 109.33(16) ?
N2 C10 C11 . . 106.68(15) ?
C12 C10 C11 . . 110.80(17) ?
N2 C10 C13 . . 100.34(14) ?
C12 C10 C13 . . 115.19(16) ?
C11 C10 C13 . . 113.58(17) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C10 C12 H12A . . 109.5 ?
C10 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C10 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N3 C13 C15 . . 110.02(16) ?
N3 C13 C14 . . 106.34(15) ?
C15 C13 C14 . . 110.62(19) ?
N3 C13 C10 . . 99.78(14) ?
C15 C13 C10 . . 115.44(17) ?
C14 C13 C10 . . 113.69(17) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C13 C15 H15A . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C13 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 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 C8 . 1.346(3) ?
N1 C1 . 1.377(3) ?
N1 H1 . 0.8600 ?
N2 O1 . 1.276(2) ?
N2 C9 . 1.352(2) ?
N2 C10 . 1.502(2) ?
N3 O2 . 1.287(2) ?
N3 C9 . 1.346(2) ?
N3 C13 . 1.496(2) ?
C1 C2 . 1.397(3) ?
C1 C6 . 1.407(3) ?
C2 C3 . 1.362(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.396(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.384(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.400(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.449(3) ?
C7 C8 . 1.381(3) ?
C7 C9 . 1.444(3) ?
C8 H8 . 0.9300 ?
C10 C12 . 1.519(3) ?
C10 C11 . 1.529(3) ?
C10 C13 . 1.552(3) ?
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 C15 . 1.515(3) ?
C13 C14 . 1.526(3) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 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
N1 H1 O2 2_575 0.86 2.07 2.8506(18) 150
C12 H12C O2 2_565 0.96 2.51 3.434(2) 161
C14 H14C O1 2_564 0.96 2.56 3.495(2) 164
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
C8 N1 C1 C2 . . . . 178.2(2) ?
C8 N1 C1 C6 . . . . -0.2(2) ?
N1 C1 C2 C3 . . . . -179.1(2) ?
C6 C1 C2 C3 . . . . -0.9(4) ?
C1 C2 C3 C4 . . . . 0.4(4) ?
C2 C3 C4 C5 . . . . 0.8(4) ?
C3 C4 C5 C6 . . . . -1.6(4) ?
C4 C5 C6 C1 . . . . 1.1(3) ?
C4 C5 C6 C7 . . . . 179.4(2) ?
N1 C1 C6 C5 . . . . 178.64(19) ?
C2 C1 C6 C5 . . . . 0.1(3) ?
N1 C1 C6 C7 . . . . -0.1(2) ?
C2 C1 C6 C7 . . . . -178.6(2) ?
C5 C6 C7 C8 . . . . -178.0(2) ?
C1 C6 C7 C8 . . . . 0.4(2) ?
C5 C6 C7 C9 . . . . -6.0(4) ?
C1 C6 C7 C9 . . . . 172.47(19) ?
C1 N1 C8 C7 . . . . 0.5(2) ?
C9 C7 C8 N1 . . . . -172.98(19) ?
C6 C7 C8 N1 . . . . -0.5(2) ?
O2 N3 C9 N2 . . . . -167.34(17) ?
C13 N3 C9 N2 . . . . 16.6(2) ?
O2 N3 C9 C7 . . . . 14.9(3) ?
C13 N3 C9 C7 . . . . -161.20(17) ?
O1 N2 C9 N3 . . . . 175.82(17) ?
C10 N2 C9 N3 . . . . 3.0(2) ?
O1 N2 C9 C7 . . . . -6.4(3) ?
C10 N2 C9 C7 . . . . -179.20(17) ?
C8 C7 C9 N3 . . . . -163.74(19) ?
C6 C7 C9 N3 . . . . 25.5(3) ?
C8 C7 C9 N2 . . . . 18.9(3) ?
C6 C7 C9 N2 . . . . -151.90(19) ?
O1 N2 C10 C12 . . . . 45.8(2) ?
C9 N2 C10 C12 . . . . -141.06(17) ?
O1 N2 C10 C11 . . . . -74.1(2) ?
C9 N2 C10 C11 . . . . 99.07(18) ?
O1 N2 C10 C13 . . . . 167.26(16) ?
C9 N2 C10 C13 . . . . -19.56(19) ?
O2 N3 C13 C15 . . . . 34.2(3) ?
C9 N3 C13 C15 . . . . -149.50(18) ?
O2 N3 C13 C14 . . . . -85.6(2) ?
C9 N3 C13 C14 . . . . 90.7(2) ?
O2 N3 C13 C10 . . . . 155.98(16) ?
C9 N3 C13 C10 . . . . -27.72(19) ?
N2 C10 C13 N3 . . . . 25.95(17) ?
C12 C10 C13 N3 . . . . 143.19(16) ?
C11 C10 C13 N3 . . . . -87.50(18) ?
N2 C10 C13 C15 . . . . 143.77(17) ?
C12 C10 C13 C15 . . . . -99.0(2) ?
C11 C10 C13 C15 . . . . 30.3(2) ?
N2 C10 C13 C14 . . . . -86.84(18) ?
C12 C10 C13 C14 . . . . 30.4(2) ?
C11 C10 C13 C14 . . . . 159.70(17) ?
