#------------------------------------------------------------------------------
#$Date: 2008-01-13 23:15:36 +0100 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2100378.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_2100378
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       'C15 H13 N2 O2, Br'
_chemical_formula_sum          'C15 H13 Br N2 O2'
_chemical_formula_weight       333.18
_chemical_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic
;
'3-(4-Methoxy-benzyliden)-2-oxo-2,3-dihydro-
1H-imidazo[1,2-a] pyridinium bromide'
;
_symmetry_cell_setting         orthorhombic
_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                 8.851(2)
_cell_length_b                 10.014(2)
_cell_length_c                 15.895(3)
_cell_measurement_reflns_used  2956
_cell_measurement_temperature  295(2)
_cell_measurement_theta_max    25.01
_cell_measurement_theta_min    4.27
_cell_volume                   1408.8(5)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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 0.0910
_diffrn_reflns_av_sigmaI/netI  0.0556
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_l_max     18
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_number          10831
_diffrn_reflns_theta_full      25.01
_diffrn_reflns_theta_max       25.01
_diffrn_reflns_theta_min       4.27
_diffrn_standards_decay_%      0
_diffrn_standards_interval_count 'every 50 dc frames'
_diffrn_standards_interval_time ?
_diffrn_standards_number       ?
_exptl_absorpt_coefficient_mu  2.920
_exptl_absorpt_correction_T_max 0.750
_exptl_absorpt_correction_T_min 0.543
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'XEMP.Siemens Analytical Xray, 1990'
_exptl_crystal_colour          'light brown'
_exptl_crystal_density_diffrn  1.571
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     cubic
_exptl_crystal_F_000           672
_exptl_crystal_size_max        0.4
_exptl_crystal_size_mid        0.1
_exptl_crystal_size_min        0.1
_refine_diff_density_max       0.556
_refine_diff_density_min       -0.888
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.022(18)
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 0.982
_refine_ls_hydrogen_treatment  refall
_refine_ls_matrix_type         full
_refine_ls_number_parameters   217
_refine_ls_number_reflns       2472
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    0.982
_refine_ls_R_factor_all        0.0584
_refine_ls_R_factor_gt         0.0474
_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^)+(0.0716P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.1095
_refine_ls_wR_factor_ref       0.1170
_reflns_number_gt              1972
_reflns_number_total           2472
_reflns_threshold_expression   >2sigma(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 0.99966(6) 0.45159(5) 0.78893(3) 0.0583(2) Uani d . 1 . . Br
O1 0.4740(3) 0.1223(4) 0.9604(2) 0.0476(8) Uani d . 1 . . O
O2 0.2916(5) 0.3075(4) 0.5815(2) 0.0639(12) Uani d . 1 . . O
N1 0.8659(4) 0.1036(4) 0.9472(3) 0.0357(10) Uani d . 1 . . N
N2 0.6854(4) 0.0797(4) 1.0398(3) 0.0409(10) Uani d . 1 . . N
H2N 0.6502 0.0714 1.0867 0.049 Uiso d R 1 . . H
C1 0.8371(5) 0.0740(5) 1.0279(3) 0.0376(11) Uani d . 1 . . C
C2 0.9506(6) 0.0475(6) 1.0853(4) 0.0449(12) Uani d . 1 . . C
H2 0.927(5) 0.022(5) 1.136(3) 0.032(13) Uiso d . 1 . . H
C3 1.0966(5) 0.0484(6) 1.0555(4) 0.0504(14) Uani d . 1 . . C
H3 1.176(6) 0.018(5) 1.099(3) 0.059(15) Uiso d . 1 . . H
C4 1.1245(6) 0.0753(6) 0.9708(4) 0.0547(16) Uani d . 1 . . C
H4 1.210(6) 0.077(5) 0.948(3) 0.052(15) Uiso d . 1 . . H
C5 1.0139(5) 0.1045(5) 0.9172(3) 0.0430(11) Uani d . 1 . . C
H5 1.025(6) 0.145(5) 0.862(3) 0.046(13) Uiso d . 1 . . H
C6 0.7288(5) 0.1297(5) 0.9017(3) 0.0341(10) Uani d . 1 . . C
C7 0.6118(5) 0.1112(5) 0.9667(3) 0.0383(11) Uani d . 1 . . C
C8 0.7278(6) 0.1737(5) 0.8234(3) 0.0410(12) Uani d . 1 . . C
H8 0.810(6) 0.200(5) 0.806(3) 0.036(13) Uiso d . 1 . . H
C9 0.6066(6) 0.2048(5) 0.7640(3) 0.0408(12) Uani d . 1 . . C
C10 0.6441(6) 0.2786(6) 0.6934(4) 0.0512(14) Uani d . 1 . . C
H10 0.764(7) 0.309(6) 0.688(4) 0.070(17) Uiso d . 1 . . H
C11 0.5375(7) 0.3120(6) 0.6347(4) 0.0569(16) Uani d . 1 . . C
H11 0.558(6) 0.360(6) 0.590(4) 0.060(18) Uiso d . 1 . . H
C12 0.3864(6) 0.2720(5) 0.6464(4) 0.0477(13) Uani d . 1 . . C
C13 0.3482(6) 0.1987(6) 0.7150(4) 0.0492(13) Uani d . 1 . . C
H13 0.240(7) 0.156(6) 0.712(3) 0.066(17) Uiso d . 1 . . H
C14 0.4559(5) 0.1659(6) 0.7736(3) 0.0458(13) Uani d . 1 . . C
H14 0.432(6) 0.125(6) 0.824(4) 0.058(17) Uiso d . 1 . . H
C15 0.1371(7) 0.2645(7) 0.5892(4) 0.0636(17) Uani d . 1 . . C
H15A 0.1027 0.3074 0.6369 0.083 Uiso d R 1 . . H
H15B 0.1272 0.1728 0.5920 0.083 Uiso d R 1 . . H
H15C 0.0854 0.3017 0.5444 0.083 Uiso d R 1 . . H
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 0.0526(3) 0.0705(4) 0.0519(3) -0.0055(4) -0.0138(3) 0.0061(3)
O1 0.0166(18) 0.075(2) 0.0514(19) 0.0026(16) 0.0005(15) -0.0008(17)
O2 0.072(3) 0.066(3) 0.053(2) 0.003(2) -0.026(2) 0.010(2)
N1 0.0160(17) 0.042(2) 0.049(2) -0.0018(16) -0.0011(17) -0.0078(19)
N2 0.0226(18) 0.060(3) 0.040(2) -0.0029(17) 0.0027(16) -0.003(2)
C1 0.022(2) 0.041(3) 0.050(3) -0.001(2) 0.000(2) -0.001(2)
C2 0.039(3) 0.043(3) 0.053(3) 0.002(2) -0.010(2) 0.004(3)
C3 0.029(3) 0.048(3) 0.074(4) 0.003(3) -0.016(2) -0.005(3)
C4 0.018(2) 0.063(4) 0.084(5) -0.002(2) -0.002(3) -0.012(3)
C5 0.014(2) 0.053(3) 0.062(3) -0.004(2) 0.012(3) -0.008(2)
C6 0.015(2) 0.046(3) 0.042(3) 0.0022(19) -0.0015(18) -0.001(2)
C7 0.022(2) 0.047(3) 0.046(3) -0.007(2) 0.004(2) -0.007(2)
C8 0.027(3) 0.043(3) 0.053(3) -0.002(2) 0.006(2) 0.001(2)
C9 0.034(3) 0.046(3) 0.042(3) -0.002(2) 0.004(2) 0.001(2)
C10 0.044(3) 0.059(3) 0.051(3) -0.007(3) 0.003(3) 0.005(3)
C11 0.068(4) 0.055(3) 0.048(3) -0.011(3) -0.005(3) 0.015(3)
C12 0.056(3) 0.039(3) 0.048(3) 0.009(3) -0.009(3) -0.009(3)
C13 0.037(3) 0.065(4) 0.046(3) 0.002(3) 0.000(3) 0.004(3)
C14 0.033(3) 0.070(4) 0.034(3) -0.002(2) 0.000(2) 0.006(3)
C15 0.066(4) 0.064(4) 0.060(4) 0.010(3) -0.025(3) 0.000(3)
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
C12 O2 C15 . . 115.9(5) ?
C1 N1 C5 . . 120.5(4) ?
C1 N1 C6 . . 111.2(4) ?
C5 N1 C6 . . 128.3(4) ?
C1 N2 C7 . . 111.2(4) ?
C1 N2 H2N . . 120.2 ?
C7 N2 H2N . . 128.3 ?
N1 C1 N2 . . 108.2(4) ?
N1 C1 C2 . . 122.4(4) ?
N2 C1 C2 . . 129.4(5) ?
C3 C2 C1 . . 117.0(5) ?
C3 C2 H2 . . 123(3) ?
C1 C2 H2 . . 120(3) ?
C2 C3 C4 . . 120.0(5) ?
C2 C3 H3 . . 114(3) ?
C4 C3 H3 . . 126(3) ?
C5 C4 C3 . . 122.0(5) ?
C5 C4 H4 . . 112(4) ?
C3 C4 H4 . . 126(4) ?
C4 C5 N1 . . 118.2(5) ?
C4 C5 H5 . . 127(3) ?
N1 C5 H5 . . 114(3) ?
C8 C6 N1 . . 122.8(4) ?
C8 C6 C7 . . 134.3(4) ?
N1 C6 C7 . . 102.5(4) ?
O1 C7 N2 . . 124.2(4) ?
O1 C7 C6 . . 128.9(5) ?
N2 C7 C6 . . 106.9(4) ?
C6 C8 C9 . . 133.2(5) ?
C6 C8 H8 . . 115(3) ?
C9 C8 H8 . . 111(3) ?
C10 C9 C14 . . 117.8(6) ?
C10 C9 C8 . . 117.5(5) ?
C14 C9 C8 . . 124.7(5) ?
C11 C10 C9 . . 121.2(5) ?
C11 C10 H10 . . 123(3) ?
C9 C10 H10 . . 116(3) ?
C10 C11 C12 . . 119.7(5) ?
C10 C11 H11 . . 123(4) ?
C12 C11 H11 . . 118(4) ?
C13 C12 O2 . . 126.2(5) ?
C13 C12 C11 . . 119.7(5) ?
O2 C12 C11 . . 114.0(5) ?
C12 C13 C14 . . 120.2(5) ?
C12 C13 H13 . . 114(3) ?
C14 C13 H13 . . 124(3) ?
C13 C14 C9 . . 121.4(5) ?
C13 C14 H14 . . 122(3) ?
C9 C14 H14 . . 116(3) ?
O2 C15 H15A . . 104.1 ?
O2 C15 H15B . . 113.1 ?
H15A C15 H15B . . 113.0 ?
O2 C15 H15C . . 106.5 ?
H15A C15 H15C . . 106.3 ?
H15B C15 H15C . . 113.0 ?
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 C7 . 1.229(5) ?
O2 C12 . 1.376(6) ?
O2 C15 . 1.439(8) ?
N1 C1 . 1.342(6) ?
N1 C5 . 1.394(6) ?
N1 C6 . 1.437(6) ?
N2 C1 . 1.357(5) ?
N2 C7 . 1.369(6) ?
N2 H2N . 0.8118 ?
C1 C2 . 1.382(7) ?
C2 C3 . 1.376(8) ?
C2 H2 . 0.87(5) ?
C3 C4 . 1.395(9) ?
C3 H3 . 1.03(6) ?
C4 C5 . 1.330(8) ?
C4 H4 . 0.84(5) ?
C5 H5 . 0.98(5) ?
C6 C8 . 1.320(7) ?
C6 C7 . 1.475(6) ?
C8 C9 . 1.462(7) ?
C8 H8 . 0.82(5) ?
C9 C10 . 1.384(7) ?
C9 C14 . 1.398(8) ?
C10 C11 . 1.368(8) ?
C10 H10 . 1.11(6) ?
C11 C12 . 1.408(8) ?
C11 H11 . 0.87(6) ?
C12 C13 . 1.357(8) ?
C13 C14 . 1.374(8) ?
C13 H13 . 1.05(6) ?
C14 H14 . 0.92(6) ?
C15 H15A . 0.9240 ?
C15 H15B . 0.9240 ?
C15 H15C . 0.9241 ?
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 . . . . -179.7(4) ?
C6 N1 C1 N2 . . . . -0.5(6) ?
C5 N1 C1 C2 . . . . 2.1(8) ?
C6 N1 C1 C2 . . . . -178.6(5) ?
C7 N2 C1 N1 . . . . 1.0(6) ?
C7 N2 C1 C2 . . . . 179.0(5) ?
N1 C1 C2 C3 . . . . -2.1(9) ?
N2 C1 C2 C3 . . . . -179.9(6) ?
C1 C2 C3 C4 . . . . 0.0(10) ?
C2 C3 C4 C5 . . . . 2.1(10) ?
C3 C4 C5 N1 . . . . -2.1(8) ?
C1 N1 C5 C4 . . . . 0.0(7) ?
C6 N1 C5 C4 . . . . -179.1(5) ?
C1 N1 C6 C8 . . . . 173.2(5) ?
C5 N1 C6 C8 . . . . -7.6(8) ?
C1 N1 C6 C7 . . . . -0.2(5) ?
C5 N1 C6 C7 . . . . 179.0(4) ?
C1 N2 C7 O1 . . . . 179.8(5) ?
C1 N2 C7 C6 . . . . -1.1(6) ?
C8 C6 C7 O1 . . . . 7.5(10) ?
N1 C6 C7 O1 . . . . 179.8(5) ?
C8 C6 C7 N2 . . . . -171.5(6) ?
N1 C6 C7 N2 . . . . 0.7(5) ?
N1 C6 C8 C9 . . . . 178.6(5) ?
C7 C6 C8 C9 . . . . -10.4(10) ?
C6 C8 C9 C10 . . . . 165.1(6) ?
C6 C8 C9 C14 . . . . -14.7(9) ?
C14 C9 C10 C11 . . . . -0.2(9) ?
C8 C9 C10 C11 . . . . 180.0(5) ?
C9 C10 C11 C12 . . . . 0.6(10) ?
C15 O2 C12 C13 . . . . 1.5(8) ?
C15 O2 C12 C11 . . . . 177.8(5) ?
C10 C11 C12 C13 . . . . -1.2(9) ?
C10 C11 C12 O2 . . . . -177.7(5) ?
O2 C12 C13 C14 . . . . 177.4(5) ?
C11 C12 C13 C14 . . . . 1.3(9) ?
C12 C13 C14 C9 . . . . -0.8(9) ?
C10 C9 C14 C13 . . . . 0.3(8) ?
C8 C9 C14 C13 . . . . -179.9(5) ?