#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2223368.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_2223368
loop_
_publ_author_name
'Tarasov, Andrii V.'
'Volovnenko, Tatyana A.'
'Lugan, No\"el'
'Volovenko, Yulian M.'
_publ_section_title
;
10-Methoxybenzo[g]imidazo[1,2-a][1,8]naphthyridine-4-carbonitrile
;
_journal_coeditor_code FJ2229
_journal_issue 10
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o2524
_journal_page_last o2525
_journal_volume 65
_journal_year 2009
_chemical_formula_iupac 'C16 H10 N4 O'
_chemical_formula_moiety 'C16 H10 N4 O'
_chemical_formula_sum 'C16 H10 N4 O'
_chemical_formula_weight 274.28
_chemical_name_systematic
;
10-Methoxybenzo[g]imidazo[1,2-a][1,8]naphthyridine-4-carbonitrile
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method 'WinGX routine CIF_UPDATE'
_cell_angle_alpha 90
_cell_angle_beta 93.55(3)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 7.710(2)
_cell_length_b 11.970(2)
_cell_length_c 13.340(3)
_cell_measurement_reflns_used 9999
_cell_measurement_temperature 180(2)
_cell_measurement_theta_max 34.90
_cell_measurement_theta_min 2.65
_cell_volume 1228.8(5)
_computing_cell_refinement 'sAINT (Bruker (2007)'
_computing_data_collection 'APEX2 (Bruker, 2007)'
_computing_data_reduction 'SAINT (Bruker (2007)'
_computing_molecular_graphics
;
ORTEP3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al.,
1993)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and publCIF (Westrip, 2009)
;
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution 'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature 180(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker APEXII'
_diffrn_measurement_method \f
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0497
_diffrn_reflns_av_sigmaI/netI 0.0239
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 45253
_diffrn_reflns_theta_full 29.83
_diffrn_reflns_theta_max 29.83
_diffrn_reflns_theta_min 2.29
_diffrn_standards_decay_% 0
_diffrn_standards_interval_count 0
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.099
_exptl_absorpt_correction_T_max 0.97
_exptl_absorpt_correction_T_min 0.95
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2007)'
_exptl_crystal_colour brown
_exptl_crystal_density_diffrn 1.483
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 568
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.35
_refine_diff_density_max 0.325
_refine_diff_density_min -0.335
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.083
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_constraints 0
_refine_ls_number_parameters 191
_refine_ls_number_reflns 3532
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.083
_refine_ls_R_factor_all 0.0827
_refine_ls_R_factor_gt 0.0516
_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^)+(0.0616P)^2^+1.0259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1299
_refine_ls_wR_factor_ref 0.1638
_reflns_number_gt 2507
_reflns_number_total 3532
_reflns_threshold_expression I>2\s(I)
_[local]_cod_data_source_file fj2229.cif
_[local]_cod_data_source_block I
_[local]_cod_cif_authors_sg_H-M 'P 21/c'
_cod_database_code 2223368
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C C1 0.1160(2) 0.16186(14) 0.60289(12) 0.0239(3) Uani d . 1
C C2 0.0449(2) 0.22693(14) 0.51977(13) 0.0257(3) Uani d . 1
C C3 0.0661(2) 0.19331(15) 0.42439(13) 0.0264(4) Uani d . 1
H H3 0.0201 0.2358 0.3708 0.032 Uiso calc R 1
C C4 0.1593(2) 0.09249(14) 0.40567(12) 0.0239(3) Uani d . 1
C C5 0.1800(2) 0.05231(15) 0.31021(13) 0.0271(4) Uani d . 1
H H5 0.1352 0.0921 0.2546 0.033 Uiso calc R 1
C C6 0.2686(2) -0.04838(15) 0.29677(12) 0.0262(4) Uani d . 1
C C7 0.2865(3) -0.09560(17) 0.20044(13) 0.0339(4) Uani d . 1
H H7 0.2407 -0.0588 0.1433 0.041 Uiso calc R 1
C C8 0.3705(3) -0.19467(18) 0.19165(15) 0.0378(5) Uani d . 1
H H8 0.3800 -0.2260 0.1284 0.045 Uiso calc R 1
C C9 0.4435(3) -0.25045(16) 0.27749(15) 0.0344(4) Uani d . 1
H H9 0.5029 -0.3173 0.2698 0.041 Uiso calc R 1
C C10 0.4285(2) -0.20791(14) 0.37173(13) 0.0268(4) Uani d . 1
C C11 0.3374(2) -0.10535(14) 0.38426(12) 0.0232(3) Uani d . 1
C C12 0.2307(2) 0.02653(14) 0.48692(12) 0.0222(3) Uani d . 1
C C13 0.2521(2) 0.01703(15) 0.67504(13) 0.0282(4) Uani d . 1
H H13 0.3126 -0.0494 0.6869 0.034 Uiso calc R 1
C C14 0.1924(3) 0.08839(16) 0.74444(14) 0.0329(4) Uani d . 1
H H14 0.2065 0.0773 0.8135 0.039 Uiso calc R 1
C C15 -0.0484(2) 0.32689(16) 0.54198(14) 0.0307(4) Uani d . 1
C C16 0.5661(3) -0.36456(17) 0.45063(18) 0.0399(5) Uani d . 1
H H16A 0.4794 -0.4139 0.4207 0.060 Uiso calc R 1
H H16B 0.6029 -0.3913 0.5164 0.060 Uiso calc R 1
H H16C 0.6639 -0.3621 0.4095 0.060 Uiso calc R 1
N N1 0.1082(2) 0.17940(14) 0.69986(11) 0.0311(3) Uani d . 1
N N2 0.31704(18) -0.06777(12) 0.47856(10) 0.0231(3) Uani d . 1
N N3 0.20387(18) 0.06431(12) 0.58360(10) 0.0233(3) Uani d . 1
N N4 -0.1221(3) 0.40663(16) 0.55947(15) 0.0451(5) Uani d . 1
O O1 0.49489(18) -0.25543(11) 0.45838(10) 0.0338(3) Uani d . 1
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
C1 0.0238(8) 0.0251(8) 0.0228(8) -0.0042(6) 0.0013(6) 0.0000(6)
C2 0.0248(8) 0.0261(8) 0.0263(8) -0.0034(6) 0.0010(6) 0.0034(6)
C3 0.0277(8) 0.0265(8) 0.0248(8) -0.0023(6) -0.0009(6) 0.0060(6)
C4 0.0253(8) 0.0247(8) 0.0215(7) -0.0043(6) 0.0006(6) 0.0037(6)
C5 0.0313(9) 0.0297(8) 0.0201(7) -0.0062(7) -0.0001(6) 0.0037(6)
C6 0.0294(8) 0.0281(8) 0.0211(8) -0.0089(7) 0.0025(6) -0.0002(6)
C7 0.0440(11) 0.0377(10) 0.0205(8) -0.0124(8) 0.0049(7) -0.0007(7)
C8 0.0487(12) 0.0401(11) 0.0257(9) -0.0111(9) 0.0107(8) -0.0086(8)
C9 0.0401(10) 0.0298(9) 0.0344(10) -0.0070(8) 0.0113(8) -0.0078(7)
C10 0.0292(8) 0.0236(8) 0.0282(8) -0.0061(6) 0.0051(7) -0.0006(6)
C11 0.0249(8) 0.0237(8) 0.0213(7) -0.0074(6) 0.0031(6) -0.0008(6)
C12 0.0224(7) 0.0242(7) 0.0200(7) -0.0060(6) 0.0011(6) 0.0013(6)
C13 0.0329(9) 0.0296(8) 0.0218(8) -0.0015(7) -0.0018(6) 0.0046(6)
C14 0.0385(10) 0.0368(10) 0.0234(8) -0.0033(8) 0.0014(7) 0.0012(7)
C15 0.0314(9) 0.0321(9) 0.0285(9) -0.0003(7) 0.0019(7) 0.0026(7)
C16 0.0434(11) 0.0258(9) 0.0509(13) 0.0023(8) 0.0056(9) -0.0012(8)
N1 0.0360(8) 0.0337(8) 0.0239(7) -0.0032(6) 0.0048(6) -0.0023(6)
N2 0.0261(7) 0.0234(7) 0.0199(6) -0.0041(5) 0.0016(5) 0.0002(5)
N3 0.0260(7) 0.0237(7) 0.0199(6) -0.0025(5) 0.0000(5) 0.0009(5)
N4 0.0515(11) 0.0399(10) 0.0444(10) 0.0086(9) 0.0066(8) -0.0008(8)
O1 0.0423(8) 0.0264(6) 0.0330(7) 0.0034(6) 0.0050(6) 0.0004(5)
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 0 '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 0.006 '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
N1 C1 N3 111.76(15)
N1 C1 C2 129.36(16)
N3 C1 C2 118.86(15)
C3 C2 C1 120.12(16)
C3 C2 C15 122.18(16)
C1 C2 C15 117.70(16)
C2 C3 C4 120.31(16)
C2 C3 H3 119.8
C4 C3 H3 119.8
C5 C4 C12 116.60(16)
C5 C4 C3 122.82(15)
C12 C4 C3 120.55(15)
C4 C5 C6 120.19(16)
C4 C5 H5 119.9
C6 C5 H5 119.9
C5 C6 C7 122.25(17)
C5 C6 C11 117.77(15)
C7 C6 C11 119.95(17)
C8 C7 C6 119.94(18)
C8 C7 H7 120.0
C6 C7 H7 120.0
C7 C8 C9 120.70(18)
C7 C8 H8 119.6
C9 C8 H8 119.6
C10 C9 C8 121.13(19)
C10 C9 H9 119.4
C8 C9 H9 119.4
O1 C10 C9 125.21(17)
O1 C10 C11 114.95(15)
C9 C10 C11 119.84(17)
N2 C11 C6 122.89(16)
N2 C11 C10 118.69(15)
C6 C11 C10 118.41(15)
N2 C12 N3 117.42(14)
N2 C12 C4 125.71(15)
N3 C12 C4 116.86(15)
C14 C13 N3 105.12(16)
C14 C13 H13 127.4
N3 C13 H13 127.4
C13 C14 N1 111.80(16)
C13 C14 H14 124.1
N1 C14 H14 124.1
N4 C15 C2 179.7(2)
O1 C16 H16A 109.5
O1 C16 H16B 109.5
H16A C16 H16B 109.5
O1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C1 N1 C14 104.37(15)
C12 N2 C11 116.81(14)
C13 N3 C1 106.94(14)
C13 N3 C12 129.77(15)
C1 N3 C12 123.28(14)
C10 O1 C16 116.67(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.315(2)
C1 N3 1.382(2)
C1 C2 1.436(2)
C2 C3 1.354(2)
C2 C15 1.436(3)
C3 C4 1.434(2)
C3 H3 0.9300
C4 C5 1.380(2)
C4 C12 1.424(2)
C5 C6 1.402(3)
C5 H5 0.9300
C6 C7 1.418(2)
C6 C11 1.425(2)
C7 C8 1.360(3)
C7 H7 0.9300
C8 C9 1.412(3)
C8 H8 0.9300
C9 C10 1.368(3)
C9 H9 0.9300
C10 O1 1.360(2)
C10 C11 1.429(2)
C11 N2 1.354(2)
C12 N2 1.319(2)
C12 N3 1.394(2)
C13 C14 1.361(3)
C13 N3 1.375(2)
C13 H13 0.9300
C14 N1 1.384(3)
C14 H14 0.9300
C15 N4 1.142(3)
C16 O1 1.423(2)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
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
C8 H8 O1 4_555 0.9300 2.5000 3.366(3) 156.00
C3 H3 N1 4_565 0.9300 2.6200 3.394(2) 141.00