data_2100377
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 H14 N3 O4, Br'
_chemical_formula_sum          'C15 H14 Br N3 O4'
_chemical_formula_weight       380.20
_chemical_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic
;
'3-[Methoxy-(2-nitro-phenyl)-methyl]-2-oxo-
3H-imidazo[1,2-a]pyridinium bromide'
;
_symmetry_cell_setting         monoclinic
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 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               105.95(3)
_cell_angle_gamma              90.00
_cell_formula_units_Z          2
_cell_length_a                 7.3590(10)
_cell_length_b                 12.987(3)
_cell_length_c                 8.159(2)
_cell_measurement_reflns_used  2950
_cell_measurement_temperature  150(2)
_cell_measurement_theta_max    25.03
_cell_measurement_theta_min    5.20
_cell_volume                   749.7(3)
_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    150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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 0.0343
_diffrn_reflns_av_sigmaI/netI  0.0522
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_l_max     9
_diffrn_reflns_limit_l_min     -7
_diffrn_reflns_number          3720
_diffrn_reflns_theta_full      25.03
_diffrn_reflns_theta_max       25.03
_diffrn_reflns_theta_min       5.20
_diffrn_standards_decay_%      0
_diffrn_standards_interval_count 'every 50 dc frames'
_diffrn_standards_interval_time ?
_diffrn_standards_number       ?
_exptl_absorpt_coefficient_mu  2.766
_exptl_absorpt_correction_T_max 0.801
_exptl_absorpt_correction_T_min 0.381
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'XEMP.Siemens Analytical Xray, 1990'
_exptl_crystal_colour          yellow
_exptl_crystal_density_diffrn  1.684
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     plate
_exptl_crystal_F_000           384
_exptl_crystal_size_max        0.4
_exptl_crystal_size_mid        0.3
_exptl_crystal_size_min        0.08
_refine_diff_density_max       0.416
_refine_diff_density_min       -0.334
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.001(9)
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 0.964
_refine_ls_hydrogen_treatment  mixed
_refine_ls_matrix_type         full
_refine_ls_number_parameters   244
_refine_ls_number_reflns       1957
_refine_ls_number_restraints   1
_refine_ls_restrained_S_all    0.964
_refine_ls_R_factor_all        0.0318
_refine_ls_R_factor_gt         0.0278
_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/[\s^2^(Fo^2^)+(0.0242P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.0507
_refine_ls_wR_factor_ref       0.0518
_reflns_number_gt              1759
_reflns_number_total           1957
_reflns_threshold_expression   >2sigma(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 0.52232(5) 0.59404(4) 0.64410(5) 0.02241(12) Uani d . 1 . . Br
N1 0.8597(4) 0.4599(2) 0.4622(4) 0.0151(7) Uani d . 1 . . N
N2 0.7282(5) 0.3063(3) 0.4612(5) 0.0241(9) Uani d . 1 . . N
N3 1.2337(5) 0.6138(2) 0.9261(4) 0.0209(9) Uani d . 1 . . N
O1 0.7878(4) 0.2730(3) 0.7472(5) 0.0283(9) Uani d . 1 . . O
O3 1.1039(4) 0.6337(2) 0.7973(4) 0.0286(7) Uani d . 1 . . O
O2 1.3690(5) 0.6700(2) 0.9850(4) 0.0333(8) Uani d . 1 . . O
C1 0.7588(6) 0.3847(3) 0.3608(6) 0.0175(10) Uani d . 1 . . C
C2 0.7016(6) 0.3983(4) 0.1852(6) 0.0252(11) Uani d . 1 . . C
C3 0.7440(6) 0.4903(4) 0.1217(6) 0.0281(11) Uani d . 1 . . C
C4 0.8432(7) 0.5674(3) 0.2300(6) 0.0281(13) Uani d . 1 . . C
C5 0.8992(6) 0.5506(3) 0.4008(6) 0.0233(10) Uani d . 1 . . C
C6 0.9020(5) 0.4302(3) 0.6448(5) 0.0153(9) Uani d . 1 . . C
H6 0.8469 0.4753 0.7112 0.018 Uiso d R 1 . . H
C7 0.8015(5) 0.3263(3) 0.6314(6) 0.0188(9) Uani d . 1 . . C
C8 1.1146(6) 0.4193(3) 0.7263(5) 0.0149(9) Uani d . 1 . . C
C9 1.1631(5) 0.4253(3) 0.9213(5) 0.0150(9) Uani d . 1 . . C
C10 1.2269(6) 0.5152(3) 1.0144(5) 0.0183(9) Uani d . 1 . . C
C13 1.2089(6) 0.3399(4) 1.1941(6) 0.0235(10) Uani d . 1 . . C
C12 1.2705(7) 0.4314(4) 1.2792(7) 0.0255(12) Uani d . 1 . . C
C11 1.2810(5) 0.5189(3) 1.1893(5) 0.0213(10) Uani d . 1 . . C
H11 1.3299 0.5823 1.2444 0.026 Uiso d R 1 . . H
C14 1.1585(6) 0.3377(3) 1.0173(5) 0.0220(10) Uani d . 1 . . C
O1R 1.1646(4) 0.3228(2) 0.6671(3) 0.0172(7) Uani d . 1 . . O
C1R 1.3636(6) 0.3069(3) 0.7045(6) 0.0222(10) Uani d . 1 . . C
H1R 1.3759 0.2554 0.6200 0.029 Uiso d R 1 . . H
H2R 1.4202 0.3658 0.6785 0.029 Uiso d R 1 . . H
H3R 1.4156 0.2855 0.8136 0.029 Uiso d R 1 . . H
H2 0.636(6) 0.342(3) 0.126(5) 0.031(12) Uiso d . 1 . . H
H2A 0.669(6) 0.255(3) 0.423(5) 0.022(13) Uiso d . 1 . . H
H3 0.699(6) 0.499(3) 0.010(6) 0.028(13) Uiso d . 1 . . H
H4 0.870(6) 0.630(3) 0.181(5) 0.021(13) Uiso d . 1 . . H
H5 0.962(5) 0.591(5) 0.487(4) 0.013(9) Uiso d . 1 . . H
H8 1.169(5) 0.475(3) 0.684(4) 0.003(9) Uiso d . 1 . . H
H12 1.297(5) 0.432(3) 1.403(5) 0.022(11) Uiso d . 1 . . H
H13 1.198(5) 0.279(3) 1.253(5) 0.014(10) Uiso d . 1 . . H
H14 1.128(5) 0.278(3) 0.964(5) 0.021(12) Uiso d . 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 0.02165(19) 0.01693(18) 0.0283(2) 0.0035(2) 0.00623(14) -0.0001(3)
N1 0.0140(17) 0.0151(17) 0.0163(18) 0.0020(14) 0.0043(15) 0.0012(14)
N2 0.021(2) 0.018(2) 0.030(2) -0.0085(17) -0.0009(18) -0.0001(18)
N3 0.0252(18) 0.016(3) 0.0228(19) -0.0043(16) 0.0094(15) -0.0050(16)
O1 0.0205(18) 0.029(2) 0.035(2) -0.0052(15) 0.0071(16) 0.0122(18)
O3 0.0318(17) 0.0189(15) 0.0325(19) 0.0066(13) 0.0044(15) 0.0039(13)
O2 0.043(2) 0.0255(17) 0.0313(19) -0.0171(16) 0.0109(16) -0.0100(14)
C1 0.010(2) 0.017(2) 0.026(3) 0.0041(19) 0.007(2) 0.003(2)
C2 0.020(2) 0.029(3) 0.023(3) 0.000(2) 0.001(2) -0.006(2)
C3 0.028(3) 0.040(3) 0.015(3) 0.011(2) 0.004(2) 0.002(2)
C4 0.033(3) 0.025(4) 0.028(3) 0.0049(19) 0.010(2) 0.007(2)
C5 0.024(2) 0.017(2) 0.028(3) -0.0002(19) 0.008(2) -0.002(2)
C6 0.018(2) 0.015(2) 0.012(2) 0.0051(17) 0.0049(17) 0.0003(17)
C7 0.010(2) 0.019(2) 0.026(3) 0.0005(17) 0.0023(18) 0.004(2)
C8 0.016(2) 0.008(2) 0.021(2) -0.0004(16) 0.0049(18) -0.0024(18)
C9 0.013(2) 0.014(2) 0.017(2) 0.0022(16) 0.0023(17) -0.0029(17)
C10 0.018(2) 0.017(2) 0.021(2) 0.0032(18) 0.0068(19) 0.0043(18)
C13 0.029(3) 0.019(3) 0.024(3) 0.003(2) 0.008(2) 0.005(2)
C12 0.024(3) 0.031(3) 0.020(3) 0.004(2) 0.003(2) 0.000(2)
C11 0.017(2) 0.021(2) 0.024(3) 0.0018(18) 0.0033(19) -0.0069(19)
C14 0.026(2) 0.014(2) 0.026(3) -0.0047(19) 0.008(2) -0.004(2)
O1R 0.0125(15) 0.0150(15) 0.0216(16) 0.0019(12) 0.0006(13) -0.0053(12)
C1R 0.015(2) 0.023(2) 0.028(3) 0.006(2) 0.006(2) 0.004(2)
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 . . 122.7(4) ?
C5 N1 C6 . . 126.5(3) ?
C1 N1 C6 . . 110.6(3) ?
C1 N2 C7 . . 112.5(4) ?
C1 N2 H2A . . 123(3) ?
C7 N2 H2A . . 124(3) ?
O2 N3 O3 . . 124.3(3) ?
O2 N3 C10 . . 117.4(3) ?
O3 N3 C10 . . 118.3(3) ?
N1 C1 N2 . . 108.9(4) ?
N1 C1 C2 . . 119.8(4) ?
N2 C1 C2 . . 131.4(4) ?
C3 C2 C1 . . 117.7(4) ?
C3 C2 H2 . . 129(3) ?
C1 C2 H2 . . 114(3) ?
C2 C3 C4 . . 121.1(4) ?
C2 C3 H3 . . 116(3) ?
C4 C3 H3 . . 123(3) ?
C5 C4 C3 . . 119.4(4) ?
C5 C4 H4 . . 122(3) ?
C3 C4 H4 . . 119(3) ?
N1 C5 C4 . . 119.2(4) ?
N1 C5 H5 . . 110(3) ?
C4 C5 H5 . . 131(3) ?
N1 C6 C7 . . 101.1(3) ?
N1 C6 C8 . . 111.5(3) ?
C7 C6 C8 . . 111.5(3) ?
N1 C6 H6 . . 113.7 ?
C7 C6 H6 . . 107.9 ?
C8 C6 H6 . . 110.6 ?
O1 C7 N2 . . 126.5(4) ?
O1 C7 C6 . . 126.7(4) ?
N2 C7 C6 . . 106.8(4) ?
O1R C8 C6 . . 105.2(3) ?
O1R C8 C9 . . 112.8(3) ?
C6 C8 C9 . . 111.4(3) ?
O1R C8 H8 . . 112(2) ?
C6 C8 H8 . . 105(2) ?
C9 C8 H8 . . 110(2) ?
C14 C9 C10 . . 115.7(4) ?
C14 C9 C8 . . 120.6(4) ?
C10 C9 C8 . . 123.5(4) ?
C11 C10 C9 . . 123.4(4) ?
C11 C10 N3 . . 116.0(4) ?
C9 C10 N3 . . 120.6(3) ?
C14 C13 C12 . . 119.7(4) ?
C14 C13 H13 . . 119(2) ?
C12 C13 H13 . . 122(2) ?
C11 C12 C13 . . 120.2(5) ?
C11 C12 H12 . . 121(2) ?
C13 C12 H12 . . 118(2) ?
C12 C11 C10 . . 119.1(4) ?
C12 C11 H11 . . 122.1 ?
C10 C11 H11 . . 118.8 ?
C13 C14 C9 . . 121.9(4) ?
C13 C14 H14 . . 119(3) ?
C9 C14 H14 . . 119(3) ?
C1R O1R C8 . . 113.5(3) ?
O1R C1R H1R . . 103.6 ?
O1R C1R H2R . . 109.5 ?
H1R C1R H2R . . 105.6 ?
O1R C1R H3R . . 112.6 ?
H1R C1R H3R . . 112.5 ?
H2R C1R H3R . . 112.5 ?
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 . 1.342(5) ?
N1 C1 . 1.361(5) ?
N1 C6 . 1.487(5) ?
N2 C1 . 1.365(6) ?
N2 C7 . 1.369(5) ?
N2 H2A . 0.81(4) ?
N3 O2 . 1.221(4) ?
N3 O3 . 1.238(4) ?
N3 C10 . 1.477(5) ?
O1 C7 . 1.198(5) ?
C1 C2 . 1.389(6) ?
C2 C3 . 1.372(6) ?
C2 H2 . 0.94(4) ?
C3 C4 . 1.400(7) ?
C3 H3 . 0.89(4) ?
C4 C5 . 1.358(6) ?
C4 H4 . 0.96(4) ?
C5 H5 . 0.90(4) ?
C6 C7 . 1.528(5) ?
C6 C8 . 1.529(5) ?
C6 H6 . 0.9599 ?
C8 O1R . 1.427(5) ?
C8 C9 . 1.533(5) ?
C8 H8 . 0.93(4) ?
C9 C14 . 1.387(5) ?
C9 C10 . 1.402(5) ?
C10 C11 . 1.372(6) ?
C13 C14 . 1.387(6) ?
C13 C12 . 1.388(6) ?
C13 H13 . 0.93(4) ?
C12 C11 . 1.366(6) ?
C12 H12 . 0.97(4) ?
C11 H11 . 0.9600 ?
C14 H14 . 0.89(4) ?
O1R C1R . 1.427(5) ?
C1R H1R . 0.9820 ?
C1R H2R . 0.9224 ?
C1R H3R . 0.9110 ?
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 . . . . -174.7(4) ?
C6 N1 C1 N2 . . . . 0.4(5) ?
C5 N1 C1 C2 . . . . 3.6(6) ?
C6 N1 C1 C2 . . . . 178.8(4) ?
C7 N2 C1 N1 . . . . 1.6(5) ?
C7 N2 C1 C2 . . . . -176.5(5) ?
N1 C1 C2 C3 . . . . -2.6(6) ?
N2 C1 C2 C3 . . . . 175.4(5) ?
C1 C2 C3 C4 . . . . 0.6(7) ?
C2 C3 C4 C5 . . . . 0.4(7) ?
C1 N1 C5 C4 . . . . -2.6(6) ?
C6 N1 C5 C4 . . . . -176.9(4) ?
C3 C4 C5 N1 . . . . 0.5(6) ?
C5 N1 C6 C7 . . . . 173.0(4) ?
C1 N1 C6 C7 . . . . -2.0(4) ?
C5 N1 C6 C8 . . . . -68.4(5) ?
C1 N1 C6 C8 . . . . 116.7(4) ?
C1 N2 C7 O1 . . . . 176.5(4) ?
C1 N2 C7 C6 . . . . -2.9(5) ?
N1 C6 C7 O1 . . . . -176.5(4) ?
C8 C6 C7 O1 . . . . 64.8(6) ?
N1 C6 C7 N2 . . . . 2.8(4) ?
C8 C6 C7 N2 . . . . -115.9(4) ?
N1 C6 C8 O1R . . . . -76.8(4) ?
C7 C6 C8 O1R . . . . 35.5(4) ?
N1 C6 C8 C9 . . . . 160.7(3) ?
C7 C6 C8 C9 . . . . -87.1(4) ?
O1R C8 C9 C14 . . . . -31.3(5) ?
C6 C8 C9 C14 . . . . 86.7(4) ?
O1R C8 C9 C10 . . . . 144.0(4) ?
C6 C8 C9 C10 . . . . -97.9(4) ?
C14 C9 C10 C11 . . . . -0.4(6) ?
C8 C9 C10 C11 . . . . -175.9(4) ?
C14 C9 C10 N3 . . . . -178.6(3) ?
C8 C9 C10 N3 . . . . 5.9(6) ?
O2 N3 C10 C11 . . . . 40.9(5) ?
O3 N3 C10 C11 . . . . -139.7(4) ?
O2 N3 C10 C9 . . . . -140.8(4) ?
O3 N3 C10 C9 . . . . 38.6(5) ?
C14 C13 C12 C11 . . . . 0.2(7) ?
C13 C12 C11 C10 . . . . 1.1(7) ?
C9 C10 C11 C12 . . . . -1.0(6) ?
N3 C10 C11 C12 . . . . 177.3(4) ?
C12 C13 C14 C9 . . . . -1.6(7) ?
C10 C9 C14 C13 . . . . 1.7(6) ?
C8 C9 C14 C13 . . . . 177.4(4) ?
C6 C8 O1R C1R . . . . 169.3(3) ?
C9 C8 O1R C1R . . . . -69.1(4) ?