#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/50/1505001.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_1505001
loop_
_publ_author_name
'Loeppky, Richard N.'
'Shi, Jianzheng'
'Barnes, Charles L.'
'Geddam, Sailaja'
_publ_section_title
;
 A diazonium ion cascade from the nitrosation of tolazoline, an
 imidazoline-containing drug.
;
_journal_issue                   2
_journal_name_full               'Chemical research in toxicology'
_journal_page_first              295
_journal_page_last               307
_journal_paper_doi               10.1021/tx700317g
_journal_volume                  21
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H12 Br N3 O'
_chemical_formula_weight         270.14
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   8.9232(6)
_cell_length_b                   10.3244(7)
_cell_length_c                   12.4802(8)
_cell_measurement_reflns_used    3953
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.3
_cell_volume                     1149.76(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7129
_diffrn_reflns_theta_full        27.13
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_min         2.56
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    3.553
_exptl_absorpt_correction_T_max  0.37
_exptl_absorpt_correction_T_min  0.26
_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    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.036(10)
_refine_ls_extinction_coef       0.0025(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0238
_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)+(0.0332P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0565
_refine_ls_wR_factor_ref         0.0588
_reflns_number_gt                2180
_reflns_number_total             2535
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            tx700317g-file001.cif
_cod_data_source_block           JS0319
_cod_database_code               1505001
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
Br1 Br 0.72384(3) 0.50155(3) 0.071132(16) 0.03398(9) Uani 1 1 d .
O1 O 0.8854(2) 0.34315(18) 0.36515(16) 0.0382(5) Uani 1 1 d .
N1 N 1.1165(2) 0.1721(2) 0.23113(16) 0.0301(5) Uani 1 1 d .
H1 H 1.1292 0.1156 0.2831 0.036 Uiso 1 1 calc R
N2 N 0.9988(2) 0.3019(2) 0.12361(16) 0.0348(5) Uani 1 1 d .
H2 H 0.9225 0.3419 0.0937 0.042 Uiso 1 1 calc R
N3 N 0.7868(3) 0.2449(2) 0.33252(16) 0.0287(5) Uani 1 1 d .
C1 C 0.9872(3) 0.2197(2) 0.20346(18) 0.0250(5) Uani 1 1 d .
C2 C 1.2382(3) 0.2241(3) 0.1653(2) 0.0364(8) Uani 1 1 d .
H2A H 1.2887 0.1546 0.1242 0.044 Uiso 1 1 calc R
H2B H 1.3134 0.2698 0.2098 0.044 Uiso 1 1 calc R
C3 C 1.1558(3) 0.3183(3) 0.0908(2) 0.0392(6) Uani 1 1 d .
H3A H 1.1900 0.4085 0.1020 0.047 Uiso 1 1 calc R
H3B H 1.1702 0.2945 0.0146 0.047 Uiso 1 1 calc R
C4 C 0.8404(3) 0.1851(2) 0.25147(18) 0.0250(5) Uani 1 1 d .
C5 C 0.7532(2) 0.0796(2) 0.20113(18) 0.0251(5) Uani 1 1 d .
C6 C 0.6051(3) 0.0552(3) 0.2313(2) 0.0333(6) Uani 1 1 d .
H6 H 0.5600 0.1057 0.2861 0.040 Uiso 1 1 calc R
C7 C 0.5237(3) -0.0421(3) 0.1818(2) 0.0397(7) Uani 1 1 d .
H7 H 0.4231 -0.0581 0.2028 0.048 Uiso 1 1 calc R
C8 C 0.5887(3) -0.1162(3) 0.1018(2) 0.0386(7) Uani 1 1 d .
H8 H 0.5321 -0.1819 0.0671 0.046 Uiso 1 1 calc R
C9 C 0.7356(3) -0.0944(2) 0.0725(2) 0.0368(6) Uani 1 1 d .
H9 H 0.7810 -0.1469 0.0190 0.044 Uiso 1 1 calc R
C10 C 0.8178(2) 0.0045(3) 0.12134(17) 0.0298(5) Uani 1 1 d .
H10 H 0.9183 0.0203 0.0998 0.036 Uiso 1 1 calc R
H1O H 0.837(4) 0.374(3) 0.411(2) 0.042(9) Uiso 1 1 d .
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
Br1 0.03972(14) 0.03454(13) 0.02767(12) -0.00015(14) -0.00476(9) 0.00711(15)
O1 0.0380(11) 0.0383(11) 0.0383(11) -0.0159(9) 0.0081(9) -0.0096(9)
N1 0.0273(11) 0.0348(11) 0.0283(11) 0.0026(9) -0.0015(9) 0.0018(9)
N2 0.0355(13) 0.0356(12) 0.0333(12) 0.0080(9) 0.0056(10) 0.0059(10)
N3 0.0285(11) 0.0285(11) 0.0290(11) -0.0022(9) 0.0018(9) -0.0043(11)
C1 0.0293(13) 0.0234(12) 0.0221(11) -0.0046(9) -0.0006(10) 0.0005(10)
C2 0.0296(19) 0.0425(16) 0.0371(15) -0.0106(11) 0.0002(13) 0.0000(13)
C3 0.0418(16) 0.0385(14) 0.0371(15) 0.0025(12) 0.0109(12) -0.0028(13)
C4 0.0240(11) 0.0248(11) 0.0263(12) 0.0038(9) -0.0017(10) 0.0021(10)
C5 0.0264(14) 0.0240(12) 0.0249(11) -0.0001(9) -0.0043(10) 0.0043(9)
C6 0.0315(14) 0.0332(12) 0.0352(14) -0.0023(11) 0.0014(12) 0.0025(11)
C7 0.0290(14) 0.0394(16) 0.0505(17) -0.0019(12) -0.0056(12) -0.0024(11)
C8 0.0440(18) 0.0299(14) 0.0420(15) -0.0019(11) -0.0169(13) -0.0041(12)
C9 0.0462(17) 0.0312(13) 0.0332(13) -0.0069(10) -0.0057(13) 0.0060(12)
C10 0.0288(11) 0.0298(11) 0.0308(11) 0.0013(14) -0.0028(8) 0.0025(15)
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'
Br Br -0.2901 2.4595 '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
N3 O1 H1O 100(2)
C1 N1 C2 111.8(2)
C1 N1 H1 124.1
C2 N1 H1 124.1
C1 N2 C3 111.2(2)
C1 N2 H2 124.4
C3 N2 H2 124.4
C4 N3 O1 110.1(2)
N1 C1 N2 112.1(2)
N1 C1 C4 125.8(2)
N2 C1 C4 122.1(2)
N1 C2 C3 102.5(2)
N1 C2 H2A 111.3
C3 C2 H2A 111.3
N1 C2 H2B 111.3
C3 C2 H2B 111.3
H2A C2 H2B 109.2
N2 C3 C2 102.5(2)
N2 C3 H3A 111.3
C2 C3 H3A 111.3
N2 C3 H3B 111.3
C2 C3 H3B 111.3
H3A C3 H3B 109.2
N3 C4 C5 119.7(2)
N3 C4 C1 122.2(2)
C5 C4 C1 118.0(2)
C10 C5 C6 119.1(2)
C10 C5 C4 119.9(2)
C6 C5 C4 121.0(2)
C7 C6 C5 120.4(2)
C7 C6 H6 119.8
C5 C6 H6 119.8
C8 C7 C6 120.2(3)
C8 C7 H7 119.9
C6 C7 H7 119.9
C9 C8 C7 119.9(3)
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 C10 120.2(2)
C8 C9 H9 119.9
C10 C9 H9 119.9
C5 C10 C9 120.2(2)
C5 C10 H10 119.9
C9 C10 H10 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N3 1.403(3)
O1 H1O 0.78(3)
N1 C1 1.300(3)
N1 C2 1.464(3)
N1 H1 0.8800
N2 C1 1.313(3)
N2 C3 1.469(3)
N2 H2 0.8800
N3 C4 1.278(3)
C1 C4 1.484(3)
C2 C3 1.533(4)
C2 H2A 0.9900
C2 H2B 0.9900
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.479(3)
C5 C10 1.388(3)
C5 C6 1.397(3)
C6 C7 1.386(4)
C6 H6 0.9500
C7 C8 1.385(4)
C7 H7 0.9500
C8 C9 1.379(4)
C8 H8 0.9500
C9 C10 1.397(3)
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
C2 N1 C1 N2 0.1(3)
C2 N1 C1 C4 178.2(2)
C3 N2 C1 N1 -1.4(3)
C3 N2 C1 C4 -179.6(2)
C1 N1 C2 C3 1.2(3)
C1 N2 C3 C2 2.0(3)
N1 C2 C3 N2 -1.8(3)
O1 N3 C4 C5 -178.3(2)
O1 N3 C4 C1 0.3(3)
N1 C1 C4 N3 89.3(3)
N2 C1 C4 N3 -92.8(3)
N1 C1 C4 C5 -92.1(3)
N2 C1 C4 C5 85.8(3)
N3 C4 C5 C10 -172.5(2)
C1 C4 C5 C10 8.9(3)
N3 C4 C5 C6 8.6(3)
C1 C4 C5 C6 -170.0(2)
C10 C5 C6 C7 -0.4(4)
C4 C5 C6 C7 178.6(2)
C5 C6 C7 C8 0.0(4)
C6 C7 C8 C9 1.1(4)
C7 C8 C9 C10 -1.8(4)
C6 C5 C10 C9 -0.3(3)
C4 C5 C10 C9 -179.2(2)
C8 C9 C10 C5 1.4(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651537
