#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/50/1505004.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_1505004
loop_
_publ_author_name
'Loeppky, Richard N.'
'Shi, Jianzheng'
_publ_section_title
;
 N-nitrosotolazoline: decomposition studies of a typical
 N-nitrosoimidazoline.
;
_journal_issue                   2
_journal_name_full               'Chemical research in toxicology'
_journal_page_first              308
_journal_page_last               318
_journal_paper_doi               10.1021/tx700318k
_journal_volume                  21
_journal_year                    2008
_chemical_formula_sum            'C10 H13 N O2'
_chemical_formula_weight         179.21
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 96.2160(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3423(8)
_cell_length_b                   18.6110(14)
_cell_length_c                   4.9272(4)
_cell_measurement_reflns_used    3252
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.3
_cell_volume                     942.81(13)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6665
_diffrn_reflns_theta_full        27.14
_diffrn_reflns_theta_max         27.14
_diffrn_reflns_theta_min         1.98
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 Göttingen, Germany).
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0376
_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)+(0.0424P)²+0.2071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0965
_reflns_number_gt                1740
_reflns_number_total             2081
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            tx700318k-file001.cif
_cod_data_source_block           RL1026
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1505004
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
O1 O 0.89052(8) 0.71607(4) 0.15735(17) 0.0334(2) Uani 1 1 d .
N1 N 0.70073(9) 0.64680(5) 0.03095(18) 0.0294(2) Uani 1 1 d .
C1 C 0.91474(12) 0.60360(7) -0.0548(3) 0.0375(3) Uani 1 1 d .
H1A H 0.9085 0.6272 -0.2336 0.056 Uiso 1 1 calc R
H1B H 0.8799 0.5547 -0.0759 0.056 Uiso 1 1 calc R
H1C H 1.0061 0.6016 0.0224 0.056 Uiso 1 1 calc R
O2 O 0.63297(8) 0.66302(5) 0.44658(16) 0.0362(2) Uani 1 1 d .
C2 C 0.83757(11) 0.64554(6) 0.1334(2) 0.0278(3) Uani 1 1 d .
H2 H 0.8476 0.6222 0.3174 0.033 Uiso 1 1 calc R
C3 C 0.60825(11) 0.65784(6) 0.1973(2) 0.0275(3) Uani 1 1 d .
C4 C 0.46997(11) 0.66396(7) 0.0594(2) 0.0324(3) Uani 1 1 d .
H4A H 0.4480 0.7153 0.0290 0.039 Uiso 1 1 calc R
H4B H 0.4643 0.6401 -0.1210 0.039 Uiso 1 1 calc R
C5 C 0.37261(11) 0.63011(6) 0.2287(2) 0.0287(3) Uani 1 1 d .
C6 C 0.27345(11) 0.67018(6) 0.3238(2) 0.0309(3) Uani 1 1 d .
H6 H 0.2645 0.7196 0.2766 0.037 Uiso 1 1 calc R
C7 C 0.18722(12) 0.63914(7) 0.4869(3) 0.0367(3) Uani 1 1 d .
H7 H 0.1200 0.6673 0.5504 0.044 Uiso 1 1 calc R
C8 C 0.19904(12) 0.56745(7) 0.5568(3) 0.0398(3) Uani 1 1 d .
H8 H 0.1408 0.5462 0.6699 0.048 Uiso 1 1 calc R
C9 C 0.29656(13) 0.52661(7) 0.4606(3) 0.0406(3) Uani 1 1 d .
H9 H 0.3047 0.4771 0.5067 0.049 Uiso 1 1 calc R
C10 C 0.38209(12) 0.55771(7) 0.2977(3) 0.0364(3) Uani 1 1 d .
H10 H 0.4482 0.5292 0.2320 0.044 Uiso 1 1 calc R
H1N H 0.6768 0.6469 -0.1553 0.042(4) Uiso 1 1 d R
H1O H 0.8756 0.7364 0.3257 0.071(5) Uiso 1 1 d R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0380(5) 0.0321(5) 0.0299(5) -0.0019(3) 0.0025(4) -0.0017(3)
N1 0.0306(5) 0.0393(6) 0.0179(5) 0.0000(4) 0.0004(4) 0.0012(4)
C1 0.0366(7) 0.0429(7) 0.0324(7) -0.0072(5) 0.0007(5) 0.0061(5)
O2 0.0366(5) 0.0527(6) 0.0189(4) -0.0004(4) 0.0019(3) -0.0016(4)
C2 0.0309(6) 0.0302(6) 0.0217(5) 0.0017(4) 0.0001(4) 0.0012(4)
C3 0.0324(6) 0.0291(6) 0.0208(5) 0.0017(4) 0.0021(4) -0.0017(4)
C4 0.0315(6) 0.0422(7) 0.0233(6) 0.0030(5) 0.0021(5) 0.0014(5)
C5 0.0275(6) 0.0359(6) 0.0220(5) -0.0017(4) -0.0013(4) -0.0019(4)
C6 0.0300(6) 0.0322(6) 0.0295(6) -0.0001(5) -0.0012(5) -0.0002(4)
C7 0.0282(6) 0.0443(7) 0.0378(7) -0.0030(5) 0.0045(5) -0.0008(5)
C8 0.0331(6) 0.0477(8) 0.0388(7) 0.0050(6) 0.0046(5) -0.0099(5)
C9 0.0411(7) 0.0328(7) 0.0471(8) 0.0042(6) 0.0014(6) -0.0052(5)
C10 0.0354(7) 0.0355(7) 0.0381(7) -0.0038(5) 0.0033(5) 0.0032(5)
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
C2 O1 H1O 110.2
C3 N1 C2 121.56(9)
C3 N1 H1N 118.3
C2 N1 H1N 119.5
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O1 C2 N1 111.50(9)
O1 C2 C1 107.73(9)
N1 C2 C1 110.87(9)
O1 C2 H2 108.9
N1 C2 H2 108.9
C1 C2 H2 108.9
O2 C3 N1 122.47(11)
O2 C3 C4 121.60(10)
N1 C3 C4 115.92(10)
C5 C4 C3 111.87(9)
C5 C4 H4A 109.2
C3 C4 H4A 109.2
C5 C4 H4B 109.2
C3 C4 H4B 109.2
H4A C4 H4B 107.9
C6 C5 C10 118.21(11)
C6 C5 C4 121.46(11)
C10 C5 C4 120.32(11)
C7 C6 C5 121.01(12)
C7 C6 H6 119.5
C5 C6 H6 119.5
C8 C7 C6 120.08(12)
C8 C7 H7 120.0
C6 C7 H7 120.0
C7 C8 C9 119.53(12)
C7 C8 H8 120.2
C9 C8 H8 120.2
C10 C9 C8 120.20(12)
C10 C9 H9 119.9
C8 C9 H9 119.9
C9 C10 C5 120.96(12)
C9 C10 H10 119.5
C5 C10 H10 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.4222(14)
O1 H1O 0.9395
N1 C3 1.3410(15)
N1 C2 1.4504(15)
N1 H1N 0.9243
C1 C2 1.5057(16)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
O2 C3 1.2311(14)
C2 H2 1.0000
C3 C4 1.5197(16)
C4 C5 1.5130(16)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.3898(17)
C5 C10 1.3904(17)
C6 C7 1.3893(17)
C6 H6 0.9500
C7 C8 1.3801(19)
C7 H7 0.9500
C8 C9 1.3866(19)
C8 H8 0.9500
C9 C10 1.3841(19)
C9 H9 0.9500
C10 H10 0.9500
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
C3 N1 C2 O1 -83.47(13)
C3 N1 C2 C1 156.50(11)
C2 N1 C3 O2 -4.64(17)
C2 N1 C3 C4 175.13(10)
O2 C3 C4 C5 -36.64(16)
N1 C3 C4 C5 143.59(11)
C3 C4 C5 C6 119.36(12)
C3 C4 C5 C10 -59.39(14)
C10 C5 C6 C7 0.98(17)
C4 C5 C6 C7 -177.80(11)
C5 C6 C7 C8 -0.08(18)
C6 C7 C8 C9 -0.69(19)
C7 C8 C9 C10 0.5(2)
C8 C9 C10 C5 0.4(2)
C6 C5 C10 C9 -1.12(18)
C4 C5 C10 C9 177.67(11)
