data_2100376
loop_
_publ_author_name
'Plutecka, A.'
'Hoffmann, M.'
'Rychlewska, U.'
'Kucyba\/'la, Z.'
'P\;'aczkowski, J.'
'Pyszka, I.'
_publ_section_title
;
Relationship between structure and
photoinitiating abilities of selected
bromine salts of 2-oxo-2,3-dihydro-1H-imidazo
[1,2-a]pyridine (IMP): influence of the solvent
and the substitution in benzaldehyde on the
course of its reaction with IMP
;
_journal_issue                 1
_journal_name_full             'Acta Crystallographica, Section B'
_journal_page_first            135
_journal_page_last             142
_journal_volume                62
_journal_year                  2006
_chemical_formula_moiety       'C7 H7 N2 O, Br'
_chemical_formula_sum          'C7 H7 Br N2 O'
_chemical_formula_weight       215.06
_chemical_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic
;
'2-oxo-2,3-dihydro-1H-imidazo[1,2-a]pyridinium bromide'
;
_symmetry_cell_setting         triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M P-1
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_cell_angle_alpha              67.01(3)
_cell_angle_beta               68.03(3)
_cell_angle_gamma              72.00(3)
_cell_formula_units_Z          2
_cell_length_a                 7.2690(10)
_cell_length_b                 7.709(2)
_cell_length_c                 8.403(2)
_cell_measurement_reflns_used  2054
_cell_measurement_temperature  295(2)
_cell_measurement_theta_max    27.05
_cell_measurement_theta_min    2.92
_cell_volume                   394.61(19)
_computing_cell_refinement     'CrysAlisREDv.1.171(Oxford Diffraction,2000)'
_computing_data_collection     'CrysAlisCCDv.1.171(Oxford Diffraction,2000)'
_computing_data_reduction      'CrysAlisREDv.1.171(Oxford Diffraction,2000)'
_computing_molecular_graphics  'Simens Analytical X-Ray Instruments (1989)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature    295(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type 'Kuma KM4CCD \k-geometry diffractometer'
_diffrn_measurement_method     '\w 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 0.0351
_diffrn_reflns_av_sigmaI/netI  0.0286
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_l_max     10
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_number          4519
_diffrn_reflns_theta_full      27.05
_diffrn_reflns_theta_max       27.05
_diffrn_reflns_theta_min       2.92
_diffrn_standards_decay_%      0
_diffrn_standards_interval_count 'every 50 dc frames'
_diffrn_standards_interval_time ?
_diffrn_standards_number       ?
_exptl_absorpt_coefficient_mu  5.148
_exptl_absorpt_correction_T_max 0.592
_exptl_absorpt_correction_T_min 0.234
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'XEMP.Siemens Analytical Xray, 1990'
_exptl_crystal_colour          'light brown'
_exptl_crystal_density_diffrn  1.810
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     planar
_exptl_crystal_F_000           212
_exptl_crystal_size_max        0.4
_exptl_crystal_size_mid        0.25
_exptl_crystal_size_min        0.1
_refine_diff_density_max       0.248
_refine_diff_density_min       -0.368
_refine_ls_extinction_coef     0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method   SHELXL
_refine_ls_goodness_of_fit_ref 1.020
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_parameters   101
_refine_ls_number_reflns       1707
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.020
_refine_ls_R_factor_all        0.0239
_refine_ls_R_factor_gt         0.0196
_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/[\s^2^(Fo^2^)+(0.0288P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.0487
_refine_ls_wR_factor_ref       0.0499
_reflns_number_gt              1527
_reflns_number_total           1707
_reflns_threshold_expression   >2sigma(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
Br1 0.83766(3) 0.63871(2) 0.30079(2) 0.04169(10) Uani d . 1 . . Br
N1 0.6947(2) 0.1722(2) 0.72772(19) 0.0311(3) Uani d . 1 . . N
C1 0.7598(2) 0.0053(2) 0.8456(2) 0.0326(4) Uani d . 1 . . C
C2 0.8188(3) -0.1648(3) 0.8048(3) 0.0423(4) Uani d . 1 . . C
H2 0.8678 -0.2838 0.8855 0.051 Uiso d R 1 . . H
C3 0.8039(3) -0.1581(3) 0.6449(3) 0.0433(4) Uani d . 1 . . C
H3 0.8446 -0.2739 0.6129 0.052 Uiso d R 1 . . H
C4 0.7337(3) 0.0142(3) 0.5263(3) 0.0422(4) Uani d . 1 . . C
H4 0.7216 0.0152 0.4160 0.051 Uiso d R 1 . . H
C5 0.6801(3) 0.1803(3) 0.5700(2) 0.0374(4) Uani d . 1 . . C
H5A 0.6326 0.3004 0.4896 0.045 Uiso d R 1 . . H
C6 0.6406(3) 0.3314(3) 0.8016(3) 0.0379(4) Uani d . 1 . . C
H6A 0.7222 0.4269 0.7256 0.045 Uiso d R 1 . . H
H6B 0.5006 0.3904 0.8166 0.045 Uiso d R 1 . . H
C7 0.6842(3) 0.2318(3) 0.9828(3) 0.0404(4) Uani d . 1 . . C
N2 0.7529(2) 0.0405(2) 0.9946(2) 0.0413(4) Uani d . 1 . . N
H2A 0.7849 -0.0434 1.0784 0.050 Uiso d R 1 . . H
O1 0.6626(2) 0.3017(2) 1.0954(2) 0.0578(4) Uani d . 1 . . O
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
Br1 0.04512(14) 0.03459(13) 0.04192(13) -0.00235(8) -0.01894(9) -0.00642(8)
N1 0.0300(7) 0.0268(7) 0.0354(8) -0.0041(6) -0.0111(6) -0.0079(6)
C1 0.0305(8) 0.0287(9) 0.0355(9) -0.0050(7) -0.0112(7) -0.0060(7)
C2 0.0428(10) 0.0279(9) 0.0498(11) -0.0023(8) -0.0133(9) -0.0090(8)
C3 0.0432(10) 0.0364(11) 0.0531(12) -0.0077(8) -0.0099(9) -0.0206(9)
C4 0.0390(10) 0.0500(12) 0.0425(10) -0.0095(9) -0.0116(8) -0.0188(9)
C5 0.0353(9) 0.0390(10) 0.0355(9) -0.0074(8) -0.0140(8) -0.0052(8)
C6 0.0403(10) 0.0276(9) 0.0463(11) -0.0027(7) -0.0158(8) -0.0120(8)
C7 0.0392(10) 0.0402(10) 0.0435(10) -0.0055(8) -0.0133(8) -0.0152(8)
N2 0.0499(9) 0.0350(8) 0.0379(9) -0.0014(7) -0.0220(7) -0.0064(7)
O1 0.0712(10) 0.0564(10) 0.0567(9) -0.0014(8) -0.0254(8) -0.0304(8)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C1 . . 122.36(15) ?
C5 N1 C6 . . 127.48(15) ?
C1 N1 C6 . . 110.14(15) ?
N1 C1 N2 . . 109.19(15) ?
N1 C1 C2 . . 120.44(17) ?
N2 C1 C2 . . 130.36(17) ?
C3 C2 C1 . . 117.61(17) ?
C3 C2 H2 . . 120.8 ?
C1 C2 H2 . . 121.6 ?
C2 C3 C4 . . 121.25(17) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.4 ?
C5 C4 C3 . . 119.43(18) ?
C5 C4 H4 . . 120.7 ?
C3 C4 H4 . . 119.9 ?
N1 C5 C4 . . 118.89(17) ?
N1 C5 H5A . . 120.5 ?
C4 C5 H5A . . 120.6 ?
N1 C6 C7 . . 102.57(14) ?
N1 C6 H6A . . 111.4 ?
C7 C6 H6A . . 111.1 ?
N1 C6 H6B . . 111.2 ?
C7 C6 H6B . . 111.2 ?
H6A C6 H6B . . 109.3 ?
O1 C7 N2 . . 126.17(19) ?
O1 C7 C6 . . 128.11(19) ?
N2 C7 C6 . . 105.71(15) ?
C1 N2 C7 . . 112.38(15) ?
C1 N2 H2A . . 122.0 ?
C7 N2 H2A . . 125.6 ?
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 C5 . 1.345(2) ?
N1 C1 . 1.356(2) ?
N1 C6 . 1.470(2) ?
C1 N2 . 1.361(2) ?
C1 C2 . 1.384(3) ?
C2 C3 . 1.368(3) ?
C2 H2 . 0.9600 ?
C3 C4 . 1.395(3) ?
C3 H3 . 0.9600 ?
C4 C5 . 1.370(3) ?
C4 H4 . 0.9600 ?
C5 H5A . 0.9600 ?
C6 C7 . 1.519(3) ?
C6 H6A . 0.9601 ?
C6 H6B . 0.9600 ?
C7 O1 . 1.202(2) ?
C7 N2 . 1.379(2) ?
N2 H2A . 0.8010 ?
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
C5 N1 C1 N2 . . . . -178.23(14) ?
C6 N1 C1 N2 . . . . 0.18(19) ?
C5 N1 C1 C2 . . . . 1.5(2) ?
C6 N1 C1 C2 . . . . 179.88(16) ?
N1 C1 C2 C3 . . . . -1.6(3) ?
N2 C1 C2 C3 . . . . 178.00(18) ?
C1 C2 C3 C4 . . . . 0.7(3) ?
C2 C3 C4 C5 . . . . 0.5(3) ?
C1 N1 C5 C4 . . . . -0.2(2) ?
C6 N1 C5 C4 . . . . -178.37(16) ?
C3 C4 C5 N1 . . . . -0.7(3) ?
C5 N1 C6 C7 . . . . 178.32(15) ?
C1 N1 C6 C7 . . . . 0.01(18) ?
N1 C6 C7 O1 . . . . -179.5(2) ?
N1 C6 C7 N2 . . . . -0.19(18) ?
N1 C1 N2 C7 . . . . -0.3(2) ?
C2 C1 N2 C7 . . . . -179.98(18) ?
O1 C7 N2 C1 . . . . 179.60(19) ?
C6 C7 N2 C1 . . . . 0.3(2) ?