#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/07/2200758.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_2200758 loop_ _publ_author_name 'David W Jeffery' 'Rolf H Prager' 'Max R Taylor' _publ_section_title ; Ethyl 6-nitro-2-phenylaminoimidazo[1,2-a]pyridine-3-carboxylate ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o980 _journal_page_last o982 _journal_paper_doi 10.1107/S1600536801015574 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C16 H14 N4 O4' _chemical_formula_moiety 'C16 H14 N4 O4' _chemical_formula_sum 'C16 H14 N4 O4' _chemical_formula_weight 326.31 _chemical_melting_point 201.0(10) _chemical_name_systematic ; Ethyl 6-nitro-2-phenylaminoimidazo[1,2-a]pyridine-3-carboxylate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 104.380(10) _cell_angle_beta 92.300(10) _cell_angle_gamma 110.070(10) _cell_formula_units_Z 2 _cell_length_a 7.868(4) _cell_length_b 8.489(4) _cell_length_c 12.281(6) _cell_measurement_reflns_used 2508 _cell_measurement_temperature 168(2) _cell_measurement_theta_max 26.0 _cell_measurement_theta_min 2.7 _cell_volume 739.2(6) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Bruker, 1997)' _computing_data_reduction 'Xtal3.7 ADDREF SORTRF (Hall et al., 2000)' _computing_molecular_graphics Xtal3.7 _computing_publication_material 'Xtal3.7 BONDLA CIFIO' _computing_structure_refinement 'Xtal3.7 CRYLSQ' _computing_structure_solution 'SIR97 (Altomare et al., 1994)' _diffrn_ambient_temperature 168(2) _diffrn_measured_fraction_theta_full .99 _diffrn_measured_fraction_theta_max .99 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .03 _diffrn_reflns_av_sigmaI/netI .054 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 9625 _diffrn_reflns_theta_full 26.34 _diffrn_reflns_theta_max 26.34 _diffrn_reflns_theta_min 2.66 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .109 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_meas ? _exptl_crystal_description plate _exptl_crystal_F_000 340 _exptl_crystal_size_max .57 _exptl_crystal_size_mid .05 _exptl_crystal_size_min .035 _refine_diff_density_max .35 _refine_diff_density_min -.43 _refine_ls_abs_structure_details none _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.01 _refine_ls_goodness_of_fit_ref 1.11 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 217 _refine_ls_number_reflns 2173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all .086 _refine_ls_R_factor_gt .052 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(F~o~^2^) + (0.04F~o~^2^)^2^]^1/2^' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .095 _refine_ls_wR_factor_ref .088 _reflns_number_gt 2173 _reflns_number_total 2989 _reflns_threshold_expression Fsqd>\s(Fsqd) _cod_data_source_file tk6038.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '200-202' was changed to '201.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '200-202' was changed to '201.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_Hall -P_1 _cod_database_code 2200758 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_calc_attached_atom _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 -.2799(2) .2258(2) .41191(14) .0495(8) Uani ? ? 1.00000 ? ? O2 -.1648(2) .5073(2) .44612(13) .0386(8) Uani ? ? 1.00000 ? ? O3 .3638(2) .87524(19) .11382(12) .0347(7) Uani ? ? 1.00000 ? ? O4 .1937(2) .83149(18) .25432(12) .0325(7) Uani ? ? 1.00000 ? ? N1 .1324(2) .3158(2) -.00132(14) .0276(8) Uani ? ? 1.00000 ? ? N2 -.1906(2) .3598(3) .38705(16) .0328(9) Uani ? ? 1.00000 ? ? N3 .3374(2) .5649(2) -.05142(15) .0287(8) Uani ? ? 1.00000 ? ? N4 .0750(2) .4668(2) .16308(14) .0247(8) Uani ? ? 1.00000 ? ? C2 .2267(3) .4901(3) .01771(18) .0261(9) Uani ? ? 1.00000 ? ? C3 .1960(3) .5902(3) .11813(17) .0250(9) Uani ? ? 1.00000 ? ? C5 .0016(3) .4851(3) .26123(18) .0261(9) Uani ? ? 1.00000 ? ? C6 -.1143(3) .3379(3) .28145(18) .0269(10) Uani ? ? 1.00000 ? ? C7 -.1617(3) .1717(3) .20586(19) .0321(10) Uani ? ? 1.00000 ? ? C8 -.0836(3) .1543(3) .1095(2) .0314(10) Uani ? ? 1.00000 ? ? C9 .0402(3) .3024(3) .08636(18) .0261(9) Uani ? ? 1.00000 ? ? C10 .2604(3) .7766(3) .15997(19) .0285(10) Uani ? ? 1.00000 ? ? C11 .2431(3) 1.0191(3) .2992(2) .0374(11) Uani ? ? 1.00000 ? ? C12 .1466(3) 1.0451(3) .4000(2) .0456(12) Uani ? ? 1.00000 ? ? C13 .3876(3) .4878(3) -.15353(17) .0257(9) Uani ? ? 1.00000 ? ? C14 .5070(3) .6015(3) -.20474(19) .0295(10) Uani ? ? 1.00000 ? ? C15 .5639(3) .5360(3) -.3044(2) .0330(10) Uani ? ? 1.00000 ? ? C16 .5046(3) .3576(3) -.35488(19) .0337(11) Uani ? ? 1.00000 ? ? C17 .3852(3) .2461(3) -.30422(19) .0338(10) Uani ? ? 1.00000 ? ? C18 .3249(3) .3085(3) -.20435(18) .0303(10) Uani ? ? 1.00000 ? ? H3 .38760 .68500 -.02772 .03600 Uiso ? ? 1.00000 ? ? H5 .03002 .59664 .31390 .03300 Uiso ? ? 1.00000 ? ? H7 -.24704 .07252 .22192 .04000 Uiso ? ? 1.00000 ? ? H8 -.11255 .04201 .05760 .03900 Uiso ? ? 1.00000 ? ? H14 .54904 .72409 -.17082 .03700 Uiso ? ? 1.00000 ? ? H15 .64531 .61410 -.33914 .04100 Uiso ? ? 1.00000 ? ? H16 .54558 .31297 -.42348 .04200 Uiso ? ? 1.00000 ? ? H17 .34349 .12360 -.33866 .04200 Uiso ? ? 1.00000 ? ? H18 .24138 .23001 -.17079 .03800 Uiso ? ? 1.00000 ? ? H11a .37155 1.07461 .32075 .04700 Uiso ? ? 1.00000 ? ? H11b .20506 1.06541 .24390 .04700 Uiso ? ? 1.00000 ? ? H12a .17466 1.16653 .43268 .06800 Uiso ? ? 1.00000 ? ? H12b .18506 .99741 .45431 .06800 Uiso ? ? 1.00000 ? ? H12c .01857 .98822 .37748 .06800 Uiso ? ? 1.00000 ? ? 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 O1 .0620(12) .0368(10) .0485(11) .0099(9) .0334(9) .0174(9) O2 .0455(10) .0331(10) .0364(10) .0150(8) .0169(8) .0055(8) O3 .0396(10) .0262(9) .0362(9) .0078(7) .0163(8) .0097(7) O4 .0392(9) .0210(8) .0334(9) .0080(7) .0174(7) .0033(7) N1 .0281(10) .0262(11) .0285(11) .0087(8) .0094(9) .0083(8) N2 .0319(11) .0343(12) .0331(12) .0113(10) .0136(9) .0107(10) N3 .0328(11) .0212(10) .0290(11) .0064(8) .0124(9) .0055(8) N4 .0242(10) .0233(10) .0262(10) .0077(8) .0087(8) .0066(8) C2 .0244(12) .0260(13) .0285(13) .0093(10) .0048(10) .0081(10) C3 .0253(12) .0251(12) .0255(13) .0087(10) .0089(10) .0086(10) C5 .0289(12) .0268(12) .0230(12) .0117(10) .0083(10) .0047(9) C6 .0282(12) .0310(13) .0246(12) .0133(10) .0098(10) .0086(10) C7 .0326(13) .0261(13) .0372(15) .0076(11) .0151(12) .0111(11) C8 .0349(13) .0204(12) .0350(14) .0072(10) .0105(11) .0043(10) C9 .0256(12) .0261(12) .0268(12) .0107(10) .0058(10) .0059(10) C10 .0268(12) .0297(13) .0287(13) .0101(10) .0053(11) .0077(11) C11 .0424(14) .0220(13) .0424(15) .0070(11) .0164(12) .0046(11) C12 .0554(16) .0311(14) .0392(15) .0077(12) .0198(13) -.0001(11) C13 .0255(12) .0294(13) .0253(12) .0130(10) .0058(10) .0088(10) C14 .0304(13) .0259(13) .0324(14) .0095(10) .0099(11) .0089(11) C15 .0329(13) .0332(14) .0339(14) .0097(11) .0141(11) .0131(11) C16 .0366(14) .0381(15) .0280(13) .0155(12) .0125(11) .0078(11) C17 .0390(14) .0295(13) .0287(13) .0098(11) .0071(11) .0041(11) C18 .0314(13) .0283(13) .0292(13) .0074(11) .0104(11) .0088(10) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .002 .002 'Int Tables Vol IV Tables 2.2B and 2.3.1' H 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1' N .004 .003 'Int Tables Vol IV Tables 2.2B and 2.3.1' O .008 .006 'Int Tables Vol IV Tables 2.2B and 2.3.1' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C10 O4 C11 116.71(18) C9 N1 C2 105.10(17) O2 N2 O1 123.6(2) O2 N2 C6 119.27(19) O1 N2 C6 117.08(18) H3 N3 C2 114.99 H3 N3 C13 115.01 C2 N3 C13 130.00(17) C5 N4 C3 131.19(17) C5 N4 C9 122.07(18) C3 N4 C9 106.71(17) N3 C2 N1 125.7(2) N3 C2 C3 121.48(19) N1 C2 C3 112.8(2) C2 C3 N4 103.88(17) C2 C3 C10 127.9(2) N4 C3 C10 128.0(2) H5 C5 N4 121.3 H5 C5 C6 121.3 N4 C5 C6 117.41(18) C5 C6 C7 123.2(2) C5 C6 N2 116.66(18) C7 C6 N2 120.1(2) H7 C7 C8 120.6 H7 C7 C6 120.6 C8 C7 C6 118.9(2) H8 C8 C7 120.1 H8 C8 C9 120.1 C7 C8 C9 119.83(19) N1 C9 C8 130.00(19) N1 C9 N4 111.50(18) C8 C9 N4 118.5(2) O3 C10 O4 123.4(2) O3 C10 C3 123.7(2) O4 C10 C3 112.9(2) H11b C11 H11a 109.5 H11b C11 O4 110.27 H11b C11 C12 110.3 H11a C11 O4 110.3 H11a C11 C12 110.3 O4 C11 C12 106.15(18) H12b C12 H12c 109.5 H12b C12 H12a 109.5 H12b C12 C11 109.5 H12c C12 H12a 109.5 H12c C12 C11 109.5 H12a C12 C11 109.4 C18 C13 C14 119.8(2) C18 C13 N3 123.9(2) C14 C13 N3 116.26(18) H14 C14 C15 120.1 H14 C14 C13 120.1 C15 C14 C13 119.8(2) H15 C15 C14 119.5 H15 C15 C16 119.6 C14 C15 C16 120.9(2) H16 C16 C17 120.5 H16 C16 C15 120.5 C17 C16 C15 118.9(2) H17 C17 C16 119.3 H17 C17 C18 119.3 C16 C17 C18 121.3(2) H18 C18 C17 120.4 H18 C18 C13 120.4 C17 C18 C13 119.2(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 N2 . . 1.233(3) y O2 N2 . . 1.224(3) y O3 C10 . . 1.220(3) ? O4 C10 . . 1.336(3) ? O4 C11 . . 1.454(3) ? N1 C9 . . 1.329(3) y N1 C2 . . 1.362(3) y N2 C6 . . 1.448(3) y N3 H3 . . .920 ? N3 C2 . . 1.353(3) y N3 C13 . . 1.402(3) y N4 C5 . . 1.355(3) y N4 C3 . . 1.398(3) y N4 C9 . . 1.405(3) y C2 C3 . . 1.395(3) y C3 C10 . . 1.431(3) y C5 H5 . . .951 ? C5 C6 . . 1.358(3) y C6 C7 . . 1.397(3) y C7 H7 . . .951 ? C7 C8 . . 1.355(3) y C8 H8 . . .951 ? C8 C9 . . 1.403(3) y C11 H11b . . .950 ? C11 H11a . . .950 ? C11 C12 . . 1.488(4) ? C12 H12b . . .950 ? C12 H12c . . .950 ? C12 H12a . . .950 ? C13 C18 . . 1.392(3) ? C13 C14 . . 1.392(3) ? C14 H14 . . .951 ? C14 C15 . . 1.373(3) ? C15 H15 . . .950 ? C15 C16 . . 1.386(3) ? C16 H16 . . .951 ? C16 C17 . . 1.376(3) ? C17 H17 . . .951 ? C17 C18 . . 1.381(3) ? C18 H18 . . .950 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N3 H3 O3 .92 2.12 2.835(2) 133 yes C5 H5 O4 .95 2.28 2.832(3) 116 yes C18 H18 N1 .95 2.33 2.967(3) 124 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21132691 2 PubChem 101220593