#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/90/2229020.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_2229020
loop_
_publ_author_name
'Tian, Min'
'Xiang, Zhuo'
'Zhou, Si-Yuan'
'Jing, Lin-Lin'
'Wang, Hai-Bo'
'Sun, Xiao-Li'
_publ_section_title
;
 2-[1-(4-Chlorobenzoyl)pyrrolidin-2-yl]-4,4,5,5-tetramethyl-4,5-dihydroimidazole-1-oxyl-3-oxide
;
_journal_coeditor_code           DN2639
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o425
_journal_paper_doi               10.1107/S1600536811001462
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H23 Cl N3 O3'
_chemical_formula_moiety         'C18 H23 Cl N3 O3'
_chemical_formula_sum            'C18 H23 Cl N3 O3'
_chemical_formula_weight         364.84
_chemical_name_systematic
;
2-[1-(4-Chlorobenzoyl)pyrrolidin-2-yl]-4,4,5,5-tetramethyl-4,5-
dihydroimidazole-1-oxyl-3-oxide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 105.636(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6202(19)
_cell_length_b                   8.2694(13)
_cell_length_c                   20.315(3)
_cell_measurement_reflns_used    1006
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.09
_cell_measurement_theta_min      2.33
_cell_volume                     1879.9(5)
_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, 2008b) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008b)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0846
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9089
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.9600
_exptl_absorpt_correction_T_min  0.9281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0512
_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)+(0.0548P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1522
_reflns_number_gt                1791
_reflns_number_total             3342
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            dn2639.cif
_cod_data_source_block           I
_cod_original_cell_volume        1879.8(5)
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229020
_cod_database_fobs_code          2229020
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
Cl Cl1 0.24418(8) -0.02934(14) 0.22799(5) 0.0934(4) Uani d . 1 . .
O O1 0.61663(17) 0.1756(3) 0.04529(10) 0.0602(6) Uani d . 1 . .
O O2 0.84803(18) 0.2887(2) -0.03089(10) 0.0613(6) Uani d . 1 . .
O O3 0.7771(2) 0.5304(3) 0.15800(11) 0.0793(8) Uani d . 1 . .
N N1 0.7572(2) 0.1723(3) 0.14502(11) 0.0496(6) Uani d . 1 . .
N N2 0.81945(18) 0.3955(3) 0.00771(11) 0.0462(6) Uani d . 1 . .
N N3 0.7868(2) 0.5102(3) 0.09729(12) 0.0522(7) Uani d . 1 . .
C C1 0.3608(3) 0.0241(4) 0.19376(17) 0.0586(9) Uani d . 1 . .
C C2 0.3684(3) -0.0441(4) 0.13384(17) 0.0601(9) Uani d . 1 . .
H H2A 0.3113 -0.1182 0.1111 0.072 Uiso calc R 1 . .
C C3 0.4613(3) -0.0021(3) 0.10737(15) 0.0537(8) Uani d . 1 . .
H H3A 0.4661 -0.0471 0.0662 0.064 Uiso calc R 1 . .
C C4 0.5484(2) 0.1070(3) 0.14140(14) 0.0472(7) Uani d . 1 . .
C C5 0.5373(3) 0.1743(4) 0.20168(15) 0.0561(8) Uani d . 1 . .
H H5 0.5942 0.2480 0.2250 0.067 Uiso calc R 1 . .
C C6 0.4434(3) 0.1341(4) 0.22772(16) 0.0609(9) Uani d . 1 . .
H H6 0.4362 0.1812 0.2680 0.073 Uiso calc R 1 . .
C C7 0.6433(3) 0.1542(3) 0.10742(15) 0.0479(7) Uani d . 1 . .
C C8 0.8104(3) 0.1429(4) 0.21806(14) 0.0617(9) Uani d . 1 . .
H H8A 0.7748 0.0491 0.2335 0.074 Uiso calc R 1 . .
H H8B 0.8008 0.2360 0.2451 0.074 Uiso calc R 1 . .
C C9 0.9400(3) 0.1137(5) 0.22247(16) 0.0697(10) Uani d . 1 . .
H H9A 0.9537 0.0020 0.2121 0.084 Uiso calc R 1 . .
H H9B 0.9904 0.1401 0.2676 0.084 Uiso calc R 1 . .
C C10 0.9636(3) 0.2265(4) 0.16896(16) 0.0635(9) Uani d . 1 . .
H H10A 1.0315 0.1900 0.1537 0.076 Uiso calc R 1 . .
H H10B 0.9787 0.3357 0.1866 0.076 Uiso calc R 1 . .
C C11 0.8480(2) 0.2188(4) 0.11055(14) 0.0486(8) Uani d . 1 . .
H H11 0.8553 0.1332 0.0786 0.058 Uiso calc R 1 . .
C C12 0.8187(2) 0.3736(4) 0.07277(13) 0.0438(7) Uani d . 1 . .
C C13 0.7659(3) 0.5550(4) -0.01959(15) 0.0510(8) Uani d . 1 . .
C C14 0.7768(3) 0.6477(4) 0.04813(15) 0.0531(8) Uani d . 1 . .
C C15 0.8360(3) 0.6285(4) -0.06555(17) 0.0779(11) Uani d . 1 . .
H H15A 0.9181 0.6412 -0.0402 0.117 Uiso calc R 1 . .
H H15B 0.8029 0.7322 -0.0816 0.117 Uiso calc R 1 . .
H H15C 0.8311 0.5585 -0.1039 0.117 Uiso calc R 1 . .
C C16 0.6380(3) 0.5167(4) -0.05963(18) 0.0816(12) Uani d . 1 . .
H H16A 0.6388 0.4451 -0.0967 0.122 Uiso calc R 1 . .
H H16B 0.5976 0.6150 -0.0775 0.122 Uiso calc R 1 . .
H H16C 0.5971 0.4657 -0.0300 0.122 Uiso calc R 1 . .
C C17 0.8923(3) 0.7448(4) 0.07346(18) 0.0801(11) Uani d . 1 . .
H H17A 0.8999 0.7809 0.1193 0.120 Uiso calc R 1 . .
H H17B 0.8901 0.8367 0.0443 0.120 Uiso calc R 1 . .
H H17C 0.9593 0.6777 0.0727 0.120 Uiso calc R 1 . .
C C18 0.6703(3) 0.7508(5) 0.05121(19) 0.0856(12) Uani d . 1 . .
H H18A 0.5987 0.6872 0.0375 0.128 Uiso calc R 1 . .
H H18B 0.6643 0.8415 0.0210 0.128 Uiso calc R 1 . .
H H18C 0.6807 0.7887 0.0971 0.128 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'
Cl Cl 0.1484 0.1585 '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
C7 N1 C8 . . 129.7(2) ?
C7 N1 C11 . . 118.8(2) ?
C8 N1 C11 . . 111.4(2) ?
O2 N2 C12 . . 125.7(2) ?
O2 N2 C13 . . 122.0(2) ?
C12 N2 C13 . . 111.9(2) ?
O3 N3 C12 . . 125.4(2) ?
O3 N3 C14 . . 122.2(2) ?
C12 N3 C14 . . 112.1(2) ?
C2 C1 C6 . . 121.2(3) ?
C2 C1 Cl1 . . 119.8(3) ?
C6 C1 Cl1 . . 119.0(3) ?
C1 C2 C3 . . 119.4(3) ?
C1 C2 H2A . . 120.3 ?
C3 C2 H2A . . 120.3 ?
C2 C3 C4 . . 120.8(3) ?
C2 C3 H3A . . 119.6 ?
C4 C3 H3A . . 119.6 ?
C5 C4 C3 . . 118.2(3) ?
C5 C4 C7 . . 123.9(3) ?
C3 C4 C7 . . 117.7(3) ?
C6 C5 C4 . . 121.1(3) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C1 C6 C5 . . 119.3(3) ?
C1 C6 H6 . . 120.4 ?
C5 C6 H6 . . 120.4 ?
O1 C7 N1 . . 120.3(3) ?
O1 C7 C4 . . 119.8(3) ?
N1 C7 C4 . . 120.0(2) ?
N1 C8 C9 . . 103.3(2) ?
N1 C8 H8A . . 111.1 ?
C9 C8 H8A . . 111.1 ?
N1 C8 H8B . . 111.1 ?
C9 C8 H8B . . 111.1 ?
H8A C8 H8B . . 109.1 ?
C8 C9 C10 . . 103.4(2) ?
C8 C9 H9A . . 111.1 ?
C10 C9 H9A . . 111.1 ?
C8 C9 H9B . . 111.1 ?
C10 C9 H9B . . 111.1 ?
H9A C9 H9B . . 109.1 ?
C9 C10 C11 . . 103.9(2) ?
C9 C10 H10A . . 111.0 ?
C11 C10 H10A . . 111.0 ?
C9 C10 H10B . . 111.0 ?
C11 C10 H10B . . 111.0 ?
H10A C10 H10B . . 109.0 ?
N1 C11 C12 . . 112.2(2) ?
N1 C11 C10 . . 103.5(2) ?
C12 C11 C10 . . 113.3(2) ?
N1 C11 H11 . . 109.2 ?
C12 C11 H11 . . 109.2 ?
C10 C11 H11 . . 109.2 ?
N3 C12 N2 . . 109.4(2) ?
N3 C12 C11 . . 126.1(3) ?
N2 C12 C11 . . 124.5(3) ?
N2 C13 C15 . . 110.0(2) ?
N2 C13 C16 . . 105.2(2) ?
C15 C13 C16 . . 111.2(3) ?
N2 C13 C14 . . 100.4(2) ?
C15 C13 C14 . . 114.7(3) ?
C16 C13 C14 . . 114.3(3) ?
N3 C14 C18 . . 108.5(3) ?
N3 C14 C17 . . 105.7(2) ?
C18 C14 C17 . . 110.0(3) ?
N3 C14 C13 . . 100.9(2) ?
C18 C14 C13 . . 116.2(3) ?
C17 C14 C13 . . 114.3(3) ?
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 ?
C13 C16 H16A . . 109.5 ?
C13 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C13 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C14 C18 H18A . . 109.5 ?
C14 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C14 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 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
Cl1 C1 . 1.738(3) ?
O1 C7 . 1.229(3) ?
O2 N2 . 1.283(3) ?
O3 N3 . 1.279(3) ?
N1 C7 . 1.346(3) ?
N1 C8 . 1.466(3) ?
N1 C11 . 1.467(3) ?
N2 C12 . 1.336(3) ?
N2 C13 . 1.500(4) ?
N3 C12 . 1.328(3) ?
N3 C14 . 1.497(4) ?
C1 C2 . 1.366(4) ?
C1 C6 . 1.367(4) ?
C2 C3 . 1.374(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.392(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.382(4) ?
C4 C7 . 1.502(4) ?
C5 C6 . 1.376(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C8 C9 . 1.503(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.513(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.535(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.484(4) ?
C11 H11 . 0.9800 ?
C13 C15 . 1.521(4) ?
C13 C16 . 1.523(4) ?
C13 C14 . 1.550(4) ?
C14 C18 . 1.517(4) ?
C14 C17 . 1.529(4) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 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
C2 H2A O2 3_655 0.93 2.54 3.458(4) 170
C3 H3A O1 3_655 0.93 2.45 3.314(4) 154
C8 H8A O3 2_645 0.97 2.44 3.101(4) 125
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
C6 C1 C2 C3 . . . . 0.4(5) ?
Cl1 C1 C2 C3 . . . . -179.5(2) ?
C1 C2 C3 C4 . . . . 0.9(4) ?
C2 C3 C4 C5 . . . . -1.3(4) ?
C2 C3 C4 C7 . . . . -176.6(3) ?
C3 C4 C5 C6 . . . . 0.4(4) ?
C7 C4 C5 C6 . . . . 175.4(3) ?
C2 C1 C6 C5 . . . . -1.3(5) ?
Cl1 C1 C6 C5 . . . . 178.6(2) ?
C4 C5 C6 C1 . . . . 0.9(5) ?
C8 N1 C7 O1 . . . . -175.4(3) ?
C11 N1 C7 O1 . . . . 0.4(4) ?
C8 N1 C7 C4 . . . . 4.3(4) ?
C11 N1 C7 C4 . . . . -179.9(2) ?
C5 C4 C7 O1 . . . . -135.9(3) ?
C3 C4 C7 O1 . . . . 39.1(4) ?
C5 C4 C7 N1 . . . . 44.4(4) ?
C3 C4 C7 N1 . . . . -140.7(3) ?
C7 N1 C8 C9 . . . . 156.1(3) ?
C11 N1 C8 C9 . . . . -20.0(3) ?
N1 C8 C9 C10 . . . . 35.2(3) ?
C8 C9 C10 C11 . . . . -37.6(3) ?
C7 N1 C11 C12 . . . . 57.7(3) ?
C8 N1 C11 C12 . . . . -125.8(3) ?
C7 N1 C11 C10 . . . . -179.8(2) ?
C8 N1 C11 C10 . . . . -3.3(3) ?
C9 C10 C11 N1 . . . . 25.2(3) ?
C9 C10 C11 C12 . . . . 147.0(3) ?
O3 N3 C12 N2 . . . . 179.9(3) ?
C14 N3 C12 N2 . . . . -7.0(3) ?
O3 N3 C12 C11 . . . . 0.6(5) ?
C14 N3 C12 C11 . . . . 173.7(2) ?
O2 N2 C12 N3 . . . . 178.9(2) ?
C13 N2 C12 N3 . . . . -9.2(3) ?
O2 N2 C12 C11 . . . . -1.8(4) ?
C13 N2 C12 C11 . . . . 170.2(2) ?
N1 C11 C12 N3 . . . . 49.2(4) ?
C10 C11 C12 N3 . . . . -67.6(4) ?
N1 C11 C12 N2 . . . . -130.0(3) ?
C10 C11 C12 N2 . . . . 113.2(3) ?
O2 N2 C13 C15 . . . . -46.3(3) ?
C12 N2 C13 C15 . . . . 141.3(2) ?
O2 N2 C13 C16 . . . . 73.5(3) ?
C12 N2 C13 C16 . . . . -98.8(3) ?
O2 N2 C13 C14 . . . . -167.6(2) ?
C12 N2 C13 C14 . . . . 20.1(3) ?
O3 N3 C14 C18 . . . . -45.1(4) ?
C12 N3 C14 C18 . . . . 141.5(3) ?
O3 N3 C14 C17 . . . . 72.9(3) ?
C12 N3 C14 C17 . . . . -100.5(3) ?
O3 N3 C14 C13 . . . . -167.8(3) ?
C12 N3 C14 C13 . . . . 18.9(3) ?
N2 C13 C14 N3 . . . . -21.4(3) ?
C15 C13 C14 N3 . . . . -139.2(3) ?
C16 C13 C14 N3 . . . . 90.6(3) ?
N2 C13 C14 C18 . . . . -138.5(3) ?
C15 C13 C14 C18 . . . . 103.7(3) ?
C16 C13 C14 C18 . . . . -26.5(4) ?
N2 C13 C14 C17 . . . . 91.5(3) ?
C15 C13 C14 C17 . . . . -26.3(4) ?
C16 C13 C14 C17 . . . . -156.4(3) ?
