#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/31/2223180.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2223180
loop_
_publ_author_name
'Yaqub, Muhammad'
'Shafiq, Zahid'
'Qureshi, Ashfaq M.'
'Najam-ul-Haq, Muhammad'
_publ_section_title
'[5-(2-Furyl)-6-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-8-yl](phenyl)methanone'
_journal_coeditor_code           PV2191
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2283
_journal_paper_doi               10.1107/S1600536809033716
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H17 N3 O4'
_chemical_formula_moiety         'C18 H17 N3 O4'
_chemical_formula_sum            'C18 H17 N3 O4'
_chemical_formula_weight         339.35
_chemical_name_systematic
;
[5-(2-Furyl)-6-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-
8-yl](phenyl)methanone
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 101.94(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.980(2)
_cell_length_b                   15.047(3)
_cell_length_c                   17.932(4)
_cell_measurement_reflns_used    989
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     3162.5(11)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2001)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2001)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2001)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP area-detector'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5401
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9678
_exptl_absorpt_correction_T_min  0.9552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.362
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0551
_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)+(0.0499P)²+3.4672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                2426
_reflns_number_total             2801
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2191.cif
_cod_data_source_block           I
_cod_original_cell_volume        3162.7(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2223180
_cod_database_fobs_code          2223180
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
O O1 0.43109(14) 0.20626(10) 0.91996(10) 0.0384(4) Uani d . 1 . .
O O2 0.2016(2) 0.3319(2) 0.63070(12) 0.0835(8) Uani d . 1 . .
O O3 0.12099(18) 0.35426(18) 0.72302(12) 0.0722(7) Uani d . 1 . .
O O4 0.11567(13) 0.00988(10) 0.71141(9) 0.0319(4) Uani d . 1 . .
N N1 0.10262(16) 0.11596(13) 0.83171(10) 0.0327(5) Uani d . 1 . .
H H1A 0.0780 0.0626 0.8163 0.039 Uiso calc R 1 . .
N N2 0.21072(15) 0.23408(12) 0.84736(11) 0.0302(5) Uani d . 1 . .
N N3 0.20184(17) 0.32982(14) 0.69714(12) 0.0370(5) Uani d . 1 . .
C C1 0.05883(19) 0.16761(16) 0.88815(13) 0.0329(5) Uani d . 1 . .
H H1B 0.0652 0.1341 0.9363 0.039 Uiso calc R 1 . .
H H1C -0.0219 0.1844 0.8689 0.039 Uiso calc R 1 . .
C C2 0.1352(2) 0.2487(2) 0.89931(15) 0.0473(7) Uani d . 1 . .
H H2A 0.0902 0.3038 0.8863 0.057 Uiso calc R 1 . .
H H2B 0.1785 0.2527 0.9526 0.057 Uiso calc R 1 . .
C C3 0.18456(17) 0.15910(14) 0.80613(12) 0.0244(5) Uani d . 1 . .
C C7 0.29353(18) 0.29889(14) 0.83329(13) 0.0280(5) Uani d . 1 . .
H H7A 0.2646 0.3596 0.8419 0.034 Uiso calc R 1 . .
C C4 0.30665(18) 0.29262(15) 0.75038(13) 0.0289(5) Uani d . 1 . .
H H4A 0.3742 0.3290 0.7446 0.035 Uiso calc R 1 . .
C C5 0.32660(18) 0.19731(14) 0.72796(13) 0.0286(5) Uani d . 1 . .
H H5A 0.3265 0.1949 0.6728 0.034 Uiso calc R 1 . .
H H5B 0.4024 0.1773 0.7560 0.034 Uiso calc R 1 . .
C C6 0.23556(17) 0.13503(14) 0.74538(12) 0.0247(5) Uani d . 1 . .
C C8 0.40885(18) 0.28698(14) 0.88525(12) 0.0254(5) Uani d . 1 . .
C C9 0.5402(2) 0.21114(16) 0.96169(14) 0.0359(6) Uani d . 1 . .
H H9A 0.5781 0.1644 0.9925 0.043 Uiso calc R 1 . .
C C10 0.58593(19) 0.28997(15) 0.95339(13) 0.0312(5) Uani d . 1 . .
H H10A 0.6607 0.3094 0.9761 0.037 Uiso calc R 1 . .
C C11 0.50011(19) 0.33953(15) 0.90356(13) 0.0318(5) Uani d . 1 . .
H H11A 0.5067 0.3987 0.8866 0.038 Uiso calc R 1 . .
C C12 0.19701(17) 0.05876(14) 0.70164(12) 0.0240(5) Uani d . 1 . .
C C13 0.25482(18) 0.03347(13) 0.63770(12) 0.0243(5) Uani d . 1 . .
C C14 0.37074(19) 0.01371(15) 0.65132(14) 0.0327(5) Uani d . 1 . .
H H14A 0.4159 0.0210 0.7011 0.039 Uiso calc R 1 . .
C C15 0.4210(2) -0.01643(16) 0.59321(16) 0.0402(6) Uani d . 1 . .
H H15A 0.4997 -0.0314 0.6036 0.048 Uiso calc R 1 . .
C C16 0.3569(2) -0.02476(15) 0.52020(15) 0.0396(6) Uani d . 1 . .
H H16A 0.3916 -0.0449 0.4802 0.047 Uiso calc R 1 . .
C C17 0.2425(2) -0.00372(16) 0.50545(14) 0.0360(6) Uani d . 1 . .
H H17A 0.1987 -0.0080 0.4549 0.043 Uiso calc R 1 . .
C C18 0.19096(19) 0.02370(14) 0.56414(13) 0.0296(5) Uani d . 1 . .
H H18A 0.1114 0.0359 0.5539 0.036 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O1 C9 . . 106.02(17) ?
C3 N1 C1 . . 112.05(19) ?
C3 N1 H1A . . 124.0 ?
C1 N1 H1A . . 124.0 ?
C3 N2 C2 . . 112.04(18) ?
C3 N2 C7 . . 123.81(18) ?
C2 N2 C7 . . 123.56(19) ?
O2 N3 O3 . . 122.5(2) ?
O2 N3 C4 . . 117.9(2) ?
O3 N3 C4 . . 119.5(2) ?
N1 C1 C2 . . 103.13(18) ?
N1 C1 H1B . . 111.1 ?
C2 C1 H1B . . 111.1 ?
N1 C1 H1C . . 111.1 ?
C2 C1 H1C . . 111.1 ?
H1B C1 H1C . . 109.1 ?
N2 C2 C1 . . 103.57(19) ?
N2 C2 H2A . . 111.0 ?
C1 C2 H2A . . 111.0 ?
N2 C2 H2B . . 111.0 ?
C1 C2 H2B . . 111.0 ?
H2A C2 H2B . . 109.0 ?
N1 C3 N2 . . 108.79(19) ?
N1 C3 C6 . . 127.7(2) ?
N2 C3 C6 . . 123.53(19) ?
N2 C7 C8 . . 112.63(18) ?
N2 C7 C4 . . 109.83(17) ?
C8 C7 C4 . . 109.13(18) ?
N2 C7 H7A . . 108.4 ?
C8 C7 H7A . . 108.4 ?
C4 C7 H7A . . 108.4 ?
N3 C4 C5 . . 109.63(18) ?
N3 C4 C7 . . 110.51(18) ?
C5 C4 C7 . . 111.60(18) ?
N3 C4 H4A . . 108.3 ?
C5 C4 H4A . . 108.3 ?
C7 C4 H4A . . 108.3 ?
C6 C5 C4 . . 111.62(18) ?
C6 C5 H5A . . 109.3 ?
C4 C5 H5A . . 109.3 ?
C6 C5 H5B . . 109.3 ?
C4 C5 H5B . . 109.3 ?
H5A C5 H5B . . 108.0 ?
C3 C6 C12 . . 119.75(19) ?
C3 C6 C5 . . 116.57(19) ?
C12 C6 C5 . . 123.59(19) ?
C11 C8 O1 . . 110.01(19) ?
C11 C8 C7 . . 132.9(2) ?
O1 C8 C7 . . 117.03(18) ?
C10 C9 O1 . . 110.9(2) ?
C10 C9 H9A . . 124.5 ?
O1 C9 H9A . . 124.5 ?
C9 C10 C11 . . 106.0(2) ?
C9 C10 H10A . . 127.0 ?
C11 C10 H10A . . 127.0 ?
C8 C11 C10 . . 107.0(2) ?
C8 C11 H11A . . 126.5 ?
C10 C11 H11A . . 126.5 ?
O4 C12 C6 . . 124.7(2) ?
O4 C12 C13 . . 116.65(18) ?
C6 C12 C13 . . 118.62(18) ?
C18 C13 C14 . . 118.5(2) ?
C18 C13 C12 . . 120.01(19) ?
C14 C13 C12 . . 121.3(2) ?
C15 C14 C13 . . 120.8(2) ?
C15 C14 H14A . . 119.6 ?
C13 C14 H14A . . 119.6 ?
C16 C15 C14 . . 120.1(2) ?
C16 C15 H15A . . 120.0 ?
C14 C15 H15A . . 120.0 ?
C17 C16 C15 . . 119.8(2) ?
C17 C16 H16A . . 120.1 ?
C15 C16 H16A . . 120.1 ?
C16 C17 C18 . . 120.2(2) ?
C16 C17 H17A . . 119.9 ?
C18 C17 H17A . . 119.9 ?
C17 C18 C13 . . 120.5(2) ?
C17 C18 H18A . . 119.8 ?
C13 C18 H18A . . 119.8 ?
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 C8 . 1.366(3) ?
O1 C9 . 1.367(3) ?
O2 N3 . 1.191(3) ?
O3 N3 . 1.214(3) ?
O4 C12 . 1.262(3) ?
N1 C3 . 1.335(3) ?
N1 C1 . 1.457(3) ?
N1 H1A . 0.8800 ?
N2 C3 . 1.350(3) ?
N2 C2 . 1.443(3) ?
N2 C7 . 1.450(3) ?
N3 C4 . 1.518(3) ?
C1 C2 . 1.513(3) ?
C1 H1B . 0.9900 ?
C1 H1C . 0.9900 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C6 . 1.402(3) ?
C7 C8 . 1.509(3) ?
C7 C4 . 1.530(3) ?
C7 H7A . 1.0000 ?
C4 C5 . 1.522(3) ?
C4 H4A . 1.0000 ?
C5 C6 . 1.519(3) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C12 . 1.413(3) ?
C8 C11 . 1.334(3) ?
C9 C10 . 1.328(3) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.425(3) ?
C10 H10A . 0.9500 ?
C11 H11A . 0.9500 ?
C12 C13 . 1.506(3) ?
C13 C18 . 1.389(3) ?
C13 C14 . 1.392(3) ?
C14 C15 . 1.384(3) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.380(4) ?
C15 H15A . 0.9500 ?
C16 C17 . 1.378(4) ?
C16 H16A . 0.9500 ?
C17 C18 . 1.389(3) ?
C17 H17A . 0.9500 ?
C18 H18A . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O4 . 0.88 2.17 2.714(2) 119.2
N1 H1A O4 2_556 0.88 2.40 3.025(3) 127.8
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
C3 N1 C1 C2 . . . . -4.9(3) ?
C3 N2 C2 C1 . . . . 3.0(3) ?
C7 N2 C2 C1 . . . . 174.5(2) ?
N1 C1 C2 N2 . . . . 1.0(3) ?
C1 N1 C3 N2 . . . . 6.9(3) ?
C1 N1 C3 C6 . . . . -171.3(2) ?
C2 N2 C3 N1 . . . . -6.2(3) ?
C7 N2 C3 N1 . . . . -177.64(19) ?
C2 N2 C3 C6 . . . . 172.1(2) ?
C7 N2 C3 C6 . . . . 0.7(3) ?
C3 N2 C7 C8 . . . . -97.8(2) ?
C2 N2 C7 C8 . . . . 91.7(3) ?
C3 N2 C7 C4 . . . . 24.0(3) ?
C2 N2 C7 C4 . . . . -146.4(2) ?
O2 N3 C4 C5 . . . . -58.9(3) ?
O3 N3 C4 C5 . . . . 119.4(3) ?
O2 N3 C4 C7 . . . . 177.6(2) ?
O3 N3 C4 C7 . . . . -4.0(3) ?
N2 C7 C4 N3 . . . . 72.3(2) ?
C8 C7 C4 N3 . . . . -163.80(17) ?
N2 C7 C4 C5 . . . . -50.0(2) ?
C8 C7 C4 C5 . . . . 73.9(2) ?
N3 C4 C5 C6 . . . . -69.8(2) ?
C7 C4 C5 C6 . . . . 53.0(2) ?
N1 C3 C6 C12 . . . . 2.7(3) ?
N2 C3 C6 C12 . . . . -175.3(2) ?
N1 C3 C6 C5 . . . . 179.4(2) ?
N2 C3 C6 C5 . . . . 1.4(3) ?
C4 C5 C6 C3 . . . . -28.5(3) ?
C4 C5 C6 C12 . . . . 148.1(2) ?
C9 O1 C8 C11 . . . . 0.8(3) ?
C9 O1 C8 C7 . . . . 178.42(19) ?
N2 C7 C8 C11 . . . . -163.8(2) ?
C4 C7 C8 C11 . . . . 74.0(3) ?
N2 C7 C8 O1 . . . . 19.2(3) ?
C4 C7 C8 O1 . . . . -103.0(2) ?
C8 O1 C9 C10 . . . . -0.9(3) ?
O1 C9 C10 C11 . . . . 0.6(3) ?
O1 C8 C11 C10 . . . . -0.4(3) ?
C7 C8 C11 C10 . . . . -177.5(2) ?
C9 C10 C11 C8 . . . . -0.1(3) ?
C3 C6 C12 O4 . . . . 2.1(3) ?
C5 C6 C12 O4 . . . . -174.3(2) ?
C3 C6 C12 C13 . . . . -178.84(19) ?
C5 C6 C12 C13 . . . . 4.7(3) ?
O4 C12 C13 C18 . . . . 55.0(3) ?
C6 C12 C13 C18 . . . . -124.1(2) ?
O4 C12 C13 C14 . . . . -120.7(2) ?
C6 C12 C13 C14 . . . . 60.2(3) ?
C18 C13 C14 C15 . . . . -1.1(3) ?
C12 C13 C14 C15 . . . . 174.7(2) ?
C13 C14 C15 C16 . . . . 1.9(4) ?
C14 C15 C16 C17 . . . . -0.6(4) ?
C15 C16 C17 C18 . . . . -1.6(4) ?
C16 C17 C18 C13 . . . . 2.5(3) ?
C14 C13 C18 C17 . . . . -1.1(3) ?
C12 C13 C18 C17 . . . . -176.9(2) ?
