##############################################################################
### ###
### Electronic paper (Acta Crystallographica Section E) ###
### ###
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# #
# This CIF contains the data in a paper accepted for publication in Acta #
# Crystallographica Section E. It conforms to the requirements of Notes #
# for Authors for Section E, and has been peer reviewed under the auspices #
# of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. #
# #
# Software is freely available for graphical display of the structure(s) in #
# this CIF. For information consult the CIF home page http://www.iucr.org/ #
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data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
5-Nitro-1-nonyl-1H-benzimidazol-2(3H)-one
;
_chemical_name_common ?
_chemical_formula_moiety 'C16 H23 N3 O3'
_chemical_formula_sum 'C16 H23 N3 O3'
_chemical_formula_iupac 'C16 H23 N3 O3'
_chemical_formula_weight 305.37
_chemical_melting_point ?
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 5.4830(10)
_cell_length_b 10.2092(15)
_cell_length_c 14.746(3)
_cell_angle_alpha 74.275(9)
_cell_angle_beta 79.727(6)
_cell_angle_gamma 83.410(8)
_cell_volume 779.9(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 5537
_cell_measurement_theta_min 2.5
_cell_measurement_theta_max 34.9
_cell_measurement_temperature 90.0(5)
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.27
_exptl_crystal_size_min 0.22
_exptl_crystal_density_diffrn 1.300
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 328
_exptl_absorpt_coefficient_mu 0.091
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details
;
;
_diffrn_ambient_temperature 90.0(5)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device 'Nonius KappaCCD'
_diffrn_measurement_method '\w and \f'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 21087
_diffrn_reflns_av_R_equivalents 0.023
_diffrn_reflns_av_sigmaI/netI 0.0357
_diffrn_reflns_theta_min 2.8
_diffrn_reflns_theta_max 34.9
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_limit_l_max 22
_diffrn_standards_number .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total 6349
_reflns_number_gt 5183
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0529
_refine_ls_R_factor_gt 0.0404
_refine_ls_wR_factor_gt 0.1058
_refine_ls_wR_factor_ref 0.1129
_refine_ls_goodness_of_fit_ref 1.027
_refine_ls_restrained_S_all 1.027
_refine_ls_number_reflns 6349
_refine_ls_number_parameters 201
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.1462P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.453
_refine_diff_density_min -0.276
_refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef 0.023(5)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
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'
_computing_data_collection 'COLLECT (Nonius, 2000)'
_computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material 'SHELXL97 (Sheldrick, 2008)'
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
O O1 0.92795(11) 1.07035(6) 0.37556(4) 0.01618(12) Uani d . 1 . .
O O2 0.40529(12) 0.45052(6) 0.71989(4) 0.02109(13) Uani d . 1 . .
O O3 0.12666(12) 0.41865(6) 0.64166(5) 0.02143(13) Uani d . 1 . .
N N1 0.78463(12) 0.88673(7) 0.50035(5) 0.01369(12) Uani d . 1 . .
H H1 0.8751 0.8904 0.5431 0.016 Uiso calc R 1 . .
N N2 0.61923(12) 0.93607(7) 0.36748(4) 0.01292(12) Uani d . 1 . .
N N3 0.29292(13) 0.48382(7) 0.65097(5) 0.01591(13) Uani d . 1 . .
C C1 0.79248(13) 0.97452(8) 0.41127(5) 0.01294(13) Uani d . 1 . .
C C2 0.50448(13) 0.82444(7) 0.42883(5) 0.01255(13) Uani d . 1 . .
C C3 0.61268(13) 0.79137(8) 0.51286(5) 0.01240(13) Uani d . 1 . .
C C4 0.54726(13) 0.68061(8) 0.58770(5) 0.01379(13) Uani d . 1 . .
H H4 0.6229 0.6565 0.6437 0.017 Uiso calc R 1 . .
C C5 0.36219(13) 0.60623(7) 0.57568(5) 0.01384(13) Uani d . 1 . .
C C6 0.24677(14) 0.63920(8) 0.49481(6) 0.01500(13) Uani d . 1 . .
H H6 0.1193 0.5860 0.4912 0.018 Uiso calc R 1 . .
C C7 0.31799(14) 0.75013(8) 0.41917(5) 0.01431(13) Uani d . 1 . .
H H7 0.2421 0.7740 0.3632 0.017 Uiso calc R 1 . .
C C8 0.56136(14) 1.00911(8) 0.27295(5) 0.01453(13) Uani d . 1 . .
H H8A 0.6475 1.0948 0.2508 0.017 Uiso calc R 1 . .
H H8B 0.3804 1.0338 0.2778 0.017 Uiso calc R 1 . .
C C9 0.63787(14) 0.92606(8) 0.19926(5) 0.01496(13) Uani d . 1 . .
H H9A 0.5714 0.9758 0.1402 0.018 Uiso calc R 1 . .
H H9B 0.5589 0.8382 0.2237 0.018 Uiso calc R 1 . .
C C10 0.91760(14) 0.89612(8) 0.17380(5) 0.01536(14) Uani d . 1 . .
H H10A 0.9848 0.8397 0.2311 0.018 Uiso calc R 1 . .
H H10B 1.0005 0.9829 0.1522 0.018 Uiso calc R 1 . .
C C11 0.97314(15) 0.82089(8) 0.09493(6) 0.01648(14) Uani d . 1 . .
H H11A 0.8959 0.7325 0.1186 0.020 Uiso calc R 1 . .
H H11B 0.8936 0.8751 0.0400 0.020 Uiso calc R 1 . .
C C12 1.24889(15) 0.79376(8) 0.06003(6) 0.01714(14) Uani d . 1 . .
H H12A 1.3281 0.7349 0.1137 0.021 Uiso calc R 1 . .
H H12B 1.3293 0.8813 0.0386 0.021 Uiso calc R 1 . .
C C13 1.29159(14) 0.72462(8) -0.02204(6) 0.01650(14) Uani d . 1 . .
H H13A 1.2188 0.6349 0.0010 0.020 Uiso calc R 1 . .
H H13B 1.2018 0.7809 -0.0735 0.020 Uiso calc R 1 . .
C C14 1.56428(15) 0.70296(8) -0.06374(6) 0.01707(14) Uani d . 1 . .
H H14A 1.6346 0.7928 -0.0918 0.020 Uiso calc R 1 . .
H H14B 1.6575 0.6522 -0.0118 0.020 Uiso calc R 1 . .
C C15 1.59873(15) 0.62433(9) -0.14015(6) 0.01812(15) Uani d . 1 . .
H H15A 1.5350 0.5330 -0.1111 0.022 Uiso calc R 1 . .
H H15B 1.4981 0.6728 -0.1903 0.022 Uiso calc R 1 . .
C C16 1.86819(17) 0.60708(10) -0.18635(7) 0.02506(18) Uani d . 1 . .
H H16A 1.9271 0.6967 -0.2215 0.038 Uiso calc R 1 . .
H H16B 1.8795 0.5492 -0.2304 0.038 Uiso calc R 1 . .
H H16C 1.9712 0.5643 -0.1368 0.038 Uiso calc R 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0171(2) 0.0163(3) 0.0153(2) -0.00631(19) -0.00140(19) -0.0029(2)
O2 0.0265(3) 0.0195(3) 0.0162(3) -0.0041(2) -0.0049(2) -0.0008(2)
O3 0.0224(3) 0.0188(3) 0.0235(3) -0.0096(2) -0.0006(2) -0.0048(2)
N1 0.0147(3) 0.0147(3) 0.0125(3) -0.0040(2) -0.0026(2) -0.0035(2)
N2 0.0138(3) 0.0137(3) 0.0117(3) -0.0029(2) -0.0018(2) -0.0032(2)
N3 0.0177(3) 0.0143(3) 0.0153(3) -0.0031(2) 0.0006(2) -0.0044(2)
C1 0.0130(3) 0.0138(3) 0.0126(3) -0.0014(2) -0.0010(2) -0.0048(2)
C2 0.0120(3) 0.0132(3) 0.0126(3) -0.0014(2) -0.0005(2) -0.0043(2)
C3 0.0119(3) 0.0133(3) 0.0130(3) -0.0020(2) -0.0009(2) -0.0052(2)
C4 0.0143(3) 0.0145(3) 0.0128(3) -0.0020(2) -0.0011(2) -0.0041(2)
C5 0.0147(3) 0.0123(3) 0.0141(3) -0.0024(2) 0.0000(2) -0.0034(2)
C6 0.0140(3) 0.0150(3) 0.0168(3) -0.0028(2) -0.0017(2) -0.0051(3)
C7 0.0132(3) 0.0159(3) 0.0148(3) -0.0020(2) -0.0030(2) -0.0046(2)
C8 0.0158(3) 0.0147(3) 0.0125(3) 0.0003(2) -0.0026(2) -0.0028(2)
C9 0.0157(3) 0.0172(3) 0.0125(3) -0.0017(2) -0.0026(2) -0.0043(2)
C10 0.0163(3) 0.0171(3) 0.0135(3) -0.0011(2) -0.0024(2) -0.0053(3)
C11 0.0173(3) 0.0189(3) 0.0142(3) -0.0006(3) -0.0017(2) -0.0065(3)
C12 0.0179(3) 0.0196(4) 0.0153(3) -0.0003(3) -0.0029(3) -0.0071(3)
C13 0.0168(3) 0.0184(3) 0.0150(3) -0.0001(3) -0.0020(2) -0.0063(3)
C14 0.0173(3) 0.0181(3) 0.0157(3) -0.0004(3) -0.0015(3) -0.0053(3)
C15 0.0200(3) 0.0183(4) 0.0157(3) 0.0012(3) -0.0015(3) -0.0056(3)
C16 0.0217(4) 0.0302(5) 0.0221(4) 0.0022(3) 0.0013(3) -0.0094(3)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
O1 C1 . 1.2387(9) ?
O2 N3 . 1.2313(9) ?
O3 N3 . 1.2352(9) ?
N1 C1 . 1.3715(10) ?
N1 C3 . 1.3864(9) ?
N1 H1 . 0.8800 ?
N2 C1 . 1.3838(10) ?
N2 C2 . 1.3842(10) ?
N2 C8 . 1.4628(10) ?
N3 C5 . 1.4646(10) ?
C2 C7 . 1.3893(10) ?
C2 C3 . 1.4109(10) ?
C3 C4 . 1.3787(11) ?
C4 C5 . 1.3970(11) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3924(11) ?
C6 C7 . 1.3930(11) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C9 . 1.5266(11) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.5284(11) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.5297(11) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.5268(11) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.5303(11) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.5272(11) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.5263(11) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.5246(12) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
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
C1 N1 C3 . . 109.78(6) ?
C1 N1 H1 . . 125.1 ?
C3 N1 H1 . . 125.1 ?
C1 N2 C2 . . 109.39(6) ?
C1 N2 C8 . . 124.01(6) ?
C2 N2 C8 . . 126.52(6) ?
O2 N3 O3 . . 123.41(7) ?
O2 N3 C5 . . 118.20(7) ?
O3 N3 C5 . . 118.39(7) ?
O1 C1 N1 . . 127.21(7) ?
O1 C1 N2 . . 125.74(7) ?
N1 C1 N2 . . 107.04(6) ?
N2 C2 C7 . . 131.59(7) ?
N2 C2 C3 . . 106.99(6) ?
C7 C2 C3 . . 121.42(7) ?
C4 C3 N1 . . 131.24(7) ?
C4 C3 C2 . . 121.98(7) ?
N1 C3 C2 . . 106.77(6) ?
C3 C4 C5 . . 115.49(7) ?
C3 C4 H4 . . 122.3 ?
C5 C4 H4 . . 122.3 ?
C6 C5 C4 . . 123.69(7) ?
C6 C5 N3 . . 118.32(7) ?
C4 C5 N3 . . 117.95(7) ?
C5 C6 C7 . . 120.08(7) ?
C5 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C2 C7 C6 . . 117.29(7) ?
C2 C7 H7 . . 121.4 ?
C6 C7 H7 . . 121.4 ?
N2 C8 C9 . . 113.04(6) ?
N2 C8 H8A . . 109.0 ?
C9 C8 H8A . . 109.0 ?
N2 C8 H8B . . 109.0 ?
C9 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C8 C9 C10 . . 115.31(6) ?
C8 C9 H9A . . 108.4 ?
C10 C9 H9A . . 108.4 ?
C8 C9 H9B . . 108.4 ?
C10 C9 H9B . . 108.4 ?
H9A C9 H9B . . 107.5 ?
C9 C10 C11 . . 110.76(6) ?
C9 C10 H10A . . 109.5 ?
C11 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
C11 C10 H10B . . 109.5 ?
H10A C10 H10B . . 108.1 ?
C12 C11 C10 . . 114.85(6) ?
C12 C11 H11A . . 108.6 ?
C10 C11 H11A . . 108.6 ?
C12 C11 H11B . . 108.6 ?
C10 C11 H11B . . 108.6 ?
H11A C11 H11B . . 107.5 ?
C11 C12 C13 . . 112.22(6) ?
C11 C12 H12A . . 109.2 ?
C13 C12 H12A . . 109.2 ?
C11 C12 H12B . . 109.2 ?
C13 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
C14 C13 C12 . . 114.38(7) ?
C14 C13 H13A . . 108.7 ?
C12 C13 H13A . . 108.7 ?
C14 C13 H13B . . 108.7 ?
C12 C13 H13B . . 108.7 ?
H13A C13 H13B . . 107.6 ?
C15 C14 C13 . . 112.45(7) ?
C15 C14 H14A . . 109.1 ?
C13 C14 H14A . . 109.1 ?
C15 C14 H14B . . 109.1 ?
C13 C14 H14B . . 109.1 ?
H14A C14 H14B . . 107.8 ?
C16 C15 C14 . . 113.56(7) ?
C16 C15 H15A . . 108.9 ?
C14 C15 H15A . . 108.9 ?
C16 C15 H15B . . 108.9 ?
C14 C15 H15B . . 108.9 ?
H15A C15 H15B . . 107.7 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
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
C3 N1 C1 O1 . . . . -178.59(7) ?
C3 N1 C1 N2 . . . . 1.29(8) ?
C2 N2 C1 O1 . . . . 179.64(7) ?
C8 N2 C1 O1 . . . . -3.45(12) ?
C2 N2 C1 N1 . . . . -0.24(8) ?
C8 N2 C1 N1 . . . . 176.67(6) ?
C1 N2 C2 C7 . . . . 178.96(8) ?
C8 N2 C2 C7 . . . . 2.15(13) ?
C1 N2 C2 C3 . . . . -0.87(8) ?
C8 N2 C2 C3 . . . . -177.68(6) ?
C1 N1 C3 C4 . . . . 176.91(8) ?
C1 N1 C3 C2 . . . . -1.82(8) ?
N2 C2 C3 C4 . . . . -177.25(7) ?
C7 C2 C3 C4 . . . . 2.90(11) ?
N2 C2 C3 N1 . . . . 1.62(8) ?
C7 C2 C3 N1 . . . . -178.23(7) ?
N1 C3 C4 C5 . . . . 179.65(7) ?
C2 C3 C4 C5 . . . . -1.79(11) ?
C3 C4 C5 C6 . . . . -0.32(11) ?
C3 C4 C5 N3 . . . . 177.28(6) ?
O2 N3 C5 C6 . . . . 175.91(7) ?
O3 N3 C5 C6 . . . . -3.41(11) ?
O2 N3 C5 C4 . . . . -1.82(10) ?
O3 N3 C5 C4 . . . . 178.86(7) ?
C4 C5 C6 C7 . . . . 1.40(12) ?
N3 C5 C6 C7 . . . . -176.19(7) ?
N2 C2 C7 C6 . . . . 178.47(7) ?
C3 C2 C7 C6 . . . . -1.72(11) ?
C5 C6 C7 C2 . . . . -0.33(11) ?
C1 N2 C8 C9 . . . . 113.65(8) ?
C2 N2 C8 C9 . . . . -69.97(9) ?
N2 C8 C9 C10 . . . . -66.44(9) ?
C8 C9 C10 C11 . . . . -176.26(6) ?
C9 C10 C11 C12 . . . . 176.47(7) ?
C10 C11 C12 C13 . . . . -177.19(7) ?
C11 C12 C13 C14 . . . . 176.46(7) ?
C12 C13 C14 C15 . . . . 175.71(7) ?
C13 C14 C15 C16 . . . . 177.26(7) ?
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 O1 2_776 0.88 1.89 2.7651(9) 170
C6 H6 O3 2_566 0.95 2.58 3.3139(11) 134
_iucr_refine_instructions_details
;
TITL YO3
CELL 0.71073 5.4830 10.2092 14.7460 74.275 79.727 83.410
ZERR 2.00 0.0010 0.0015 0.0030 0.009 0.006 0.008
LATT 1
SFAC C H N O
UNIT 32 46 6 6
MERG 2
EQIV $1 2-X, 2-Y, 1-Z
HTAB N1 O1_$1
EQIV $2 -X, 1-Y, 1-Z
HTAB C6 O3_$2
FMAP 2
PLAN 20
SIZE 0.22 0.27 0.35
ACTA 50.00
BOND $H
CONF
L.S. 8
TEMP -183.00
WGHT 0.057800 0.146200
EXTI 0.023469
FVAR 1.57670
O1 4 0.927954 1.070354 0.375557 11.00000 0.01712 0.01628 =
0.01531 -0.00294 -0.00140 -0.00631
O2 4 0.405292 0.450521 0.719894 11.00000 0.02650 0.01952 =
0.01622 -0.00078 -0.00486 -0.00414
O3 4 0.126664 0.418652 0.641655 11.00000 0.02243 0.01881 =
0.02355 -0.00480 -0.00057 -0.00962
N1 3 0.784630 0.886730 0.500345 11.00000 0.01475 0.01468 =
0.01255 -0.00346 -0.00264 -0.00401
AFIX 43
H1 2 0.875143 0.890386 0.543129 11.00000 -1.20000
AFIX 0
N2 3 0.619231 0.936073 0.367481 11.00000 0.01384 0.01367 =
0.01168 -0.00325 -0.00184 -0.00288
N3 3 0.292917 0.483820 0.650970 11.00000 0.01775 0.01431 =
0.01531 -0.00438 0.00059 -0.00307
C1 1 0.792482 0.974518 0.411265 11.00000 0.01296 0.01383 =
0.01258 -0.00477 -0.00102 -0.00136
C2 1 0.504478 0.824443 0.428835 11.00000 0.01197 0.01323 =
0.01264 -0.00432 -0.00052 -0.00141
C3 1 0.612677 0.791368 0.512860 11.00000 0.01192 0.01333 =
0.01295 -0.00523 -0.00092 -0.00205
C4 1 0.547265 0.680606 0.587698 11.00000 0.01433 0.01447 =
0.01280 -0.00407 -0.00111 -0.00202
AFIX 43
H4 2 0.622945 0.656485 0.643666 11.00000 -1.20000
AFIX 0
C5 1 0.362193 0.606231 0.575681 11.00000 0.01470 0.01225 =
0.01413 -0.00342 -0.00004 -0.00243
C6 1 0.246770 0.639204 0.494806 11.00000 0.01404 0.01496 =
0.01681 -0.00515 -0.00173 -0.00283
AFIX 43
H6 2 0.119298 0.585989 0.491207 11.00000 -1.20000
AFIX 0
C7 1 0.317986 0.750129 0.419166 11.00000 0.01320 0.01586 =
0.01480 -0.00456 -0.00297 -0.00200
AFIX 43
H7 2 0.242121 0.773990 0.363247 11.00000 -1.20000
AFIX 0
C8 1 0.561358 1.009109 0.272949 11.00000 0.01580 0.01471 =
0.01253 -0.00283 -0.00263 0.00027
AFIX 23
H8A 2 0.647462 1.094816 0.250807 11.00000 -1.20000
H8B 2 0.380392 1.033756 0.277792 11.00000 -1.20000
AFIX 0
C9 1 0.637869 0.926064 0.199263 11.00000 0.01573 0.01718 =
0.01253 -0.00425 -0.00264 -0.00166
AFIX 23
H9A 2 0.571366 0.975829 0.140218 11.00000 -1.20000
H9B 2 0.558922 0.838203 0.223713 11.00000 -1.20000
AFIX 0
C10 1 0.917597 0.896124 0.173805 11.00000 0.01633 0.01710 =
0.01348 -0.00528 -0.00239 -0.00105
AFIX 23
H10A 2 0.984811 0.839683 0.231101 11.00000 -1.20000
H10B 2 1.000528 0.982854 0.152235 11.00000 -1.20000
AFIX 0
C11 1 0.973136 0.820887 0.094926 11.00000 0.01727 0.01887 =
0.01421 -0.00650 -0.00172 -0.00060
AFIX 23
H11A 2 0.895856 0.732491 0.118635 11.00000 -1.20000
H11B 2 0.893595 0.875139 0.040012 11.00000 -1.20000
AFIX 0
C12 1 1.248894 0.793760 0.060034 11.00000 0.01794 0.01959 =
0.01535 -0.00711 -0.00292 -0.00029
AFIX 23
H12A 2 1.328120 0.734891 0.113655 11.00000 -1.20000
H12B 2 1.329277 0.881278 0.038583 11.00000 -1.20000
AFIX 0
C13 1 1.291586 0.724620 -0.022041 11.00000 0.01682 0.01839 =
0.01504 -0.00628 -0.00201 -0.00008
AFIX 23
H13A 2 1.218769 0.634935 0.001012 11.00000 -1.20000
H13B 2 1.201821 0.780857 -0.073511 11.00000 -1.20000
AFIX 0
C14 1 1.564282 0.702957 -0.063735 11.00000 0.01734 0.01812 =
0.01573 -0.00526 -0.00154 -0.00042
AFIX 23
H14A 2 1.634603 0.792821 -0.091795 11.00000 -1.20000
H14B 2 1.657549 0.652243 -0.011799 11.00000 -1.20000
AFIX 0
C15 1 1.598726 0.624326 -0.140155 11.00000 0.01998 0.01833 =
0.01568 -0.00557 -0.00149 0.00122
AFIX 23
H15A 2 1.535017 0.532977 -0.111110 11.00000 -1.20000
H15B 2 1.498082 0.672814 -0.190267 11.00000 -1.20000
AFIX 0
C16 1 1.868187 0.607084 -0.186355 11.00000 0.02174 0.03021 =
0.02209 -0.00939 0.00127 0.00216
AFIX 137
H16A 2 1.927111 0.696657 -0.221497 11.00000 -1.50000
H16B 2 1.879473 0.549220 -0.230421 11.00000 -1.50000
H16C 2 1.971190 0.564293 -0.136843 11.00000 -1.50000
HKLF 4
REM YO3
REM R1 = 0.0404 for 5183 Fo > 4sig(Fo) and 0.0529 for all 6349 data
REM 201 parameters refined using 0 restraints
END
WGHT 0.0578 0.1462
REM Highest difference peak 0.453, deepest hole -0.276, 1-sigma level 0.051
Q1 1 0.4548 0.6442 0.5806 11.00000 0.05 0.45
Q2 1 0.4246 0.7894 0.4239 11.00000 0.05 0.42
Q3 1 0.2833 0.6965 0.4613 11.00000 0.05 0.42
Q4 1 0.5776 0.7373 0.5503 11.00000 0.05 0.40
Q5 1 0.5602 0.8075 0.4732 11.00000 0.05 0.39
Q6 1 0.8060 0.9257 0.4593 11.00000 0.05 0.37
Q7 1 0.7811 0.9102 0.1934 11.00000 0.05 0.37
Q8 1 1.4233 0.7165 -0.0437 11.00000 0.05 0.36
Q9 1 1.1079 0.8025 0.0794 11.00000 0.05 0.35
Q10 1 0.6873 0.9631 0.3864 11.00000 0.05 0.34
Q11 1 0.5598 0.8872 0.3983 11.00000 0.05 0.32
Q12 1 1.7323 0.6189 -0.1640 11.00000 0.05 0.31
Q13 1 0.3299 0.5492 0.6121 11.00000 0.05 0.31
Q14 1 0.3122 0.6164 0.5305 11.00000 0.05 0.31
Q15 1 0.8675 1.0203 0.3940 11.00000 0.05 0.31
Q16 1 0.7092 0.8432 0.5045 11.00000 0.05 0.30
Q17 1 0.9515 0.8529 0.1426 11.00000 0.05 0.28
Q18 1 1.6004 0.6635 -0.1012 11.00000 0.05 0.26
Q19 1 0.6166 0.9583 0.2453 11.00000 0.05 0.25
Q20 1 1.2819 0.7542 0.0180 11.00000 0.05 0.23
;
data_global
_journal_date_recd_electronic 2011-01-17
_journal_date_accepted 2011-02-15
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2011
_journal_volume 67
_journal_issue 3
_journal_page_first o669
_journal_page_last o669
_journal_paper_category QO
_journal_coeditor_code GK2342
_publ_contact_author
;
Youssef Kandri Rodi
Laboratoire de Chimie Organique Appliqu\'ee, Universit\'e Sidi Mohamed
Ben Abdallah, Facult\'e des Sciences et Techniques, Route d'immouzzer,
BP 2202 F\`es, Morocco
;
_publ_contact_author_email 'kandri_rodi@yahoo.fr'
_publ_contact_author_fax '212 537 77 54 40'
_publ_section_title
;
5-Nitro-1-nonyl-1H-benzimidazol-2(3H)-one
;
loop_
_publ_author_name
_publ_author_address
'Ouzidan, Younes'
;
Laboratoire de Chimie Organique Appliqu\'ee, Universit\'e Sidi Mohamed
Ben Abdallah, Facult\'e des Sciences et Techniques, Route d'Immouzzer,
BP 2202 F\`es, Morocco
;
'Kandri Rodi, Youssef'
;
Laboratoire de Chimie Organique Appliqu\'ee, Universit\'e Sidi Mohamed
Ben Abdallah, Facult\'e des Sciences et Techniques, Route d'Immouzzer,
BP 2202 F\`es, Morocco
;
'Essassi, El Mokhtar'
;
Laboratoire de Chimie Organique H\'et\'erocyclique, P\^ole de Comp\'etences,
Pharmacochimie, Av Ibn Battouta, BP 1014, Facult\'e des Sciences,
Universit\'e Mohammed V-Agdal, Rabat, Morocco
;
'El Ammari, Lahcen'
;
Laboratoire de Chimie du Solide Appliqu\'ee,
Facult\'e des Sciences, Universit\'e Mohammed V-Agdal
Avenue Ibn Battouta, BP. 1014, Rabat, Morocco
;
'Fronczek, Frank R.'
;
Department of Chemistry
Louisiana State University
Baton Rouge, LA 70803
USA
;
'Venkatraman, Ramaiyer'
;
Department of Chemistry and Biochemistry
Jackson State University,
Jackson
MS 39217
USA
;