#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2010699.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_2010699 loop_ _publ_author_name 'Clark, Ronald D.' 'Romero, Angela' 'Borbulevych, Oleg Ya.' 'Antipin, Mikhail Yu.' 'Nesterov, Vladimir N.' 'Timofeeva, Tatiana V.' _publ_section_title ; 2-Amino derivatives of 5-nitrophenylacetamide ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 336 _journal_page_last 338 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C11 H15 N3 O3' _chemical_formula_weight 237.26 _chemical_name_systematic ; N-[2-(isopropylamino)-5-nitrophenyl]acetamide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 103.07(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 13.408(7) _cell_length_b 13.277(4) _cell_length_c 13.577(6) _cell_measurement_reflns_used 24 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 11 _cell_measurement_theta_min 10 _cell_volume 2354.3(18) _computing_cell_refinement P3 _computing_data_collection 'P3 (Siemens, 1989)' _computing_data_reduction 'XDISK (Siemens, 1991)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXTL/PC _computing_structure_refinement SHELXTL/PC _computing_structure_solution 'SHELXTL/PC (Sheldrick, 1994)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Syntex P2~1~/PC' _diffrn_measurement_method '\q/2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .039 _diffrn_reflns_av_sigmaI/netI .047 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 4351 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_min 1.93 _diffrn_standards_decay_% 4.7 _diffrn_standards_interval_count 98 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu .099 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1008 _exptl_crystal_size_max .4 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .3 _refine_diff_density_max .20 _refine_diff_density_min -.27 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.032 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 427 _refine_ls_number_reflns 4106 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.208 _refine_ls_restrained_S_obs 1.073 _refine_ls_R_factor_all .094 _refine_ls_R_factor_gt .049 _refine_ls_shift/esd_mean .000 _refine_ls_shift/su_max .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0622P)^2^+1.0315P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all .149 _refine_ls_wR_factor_ref .110 _reflns_number_gt 2976 _reflns_number_total 4164 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm1387.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P21/n _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2010699 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 N1 .0225(10) .0237(10) .0269(10) -.0012(8) -.0023(8) .0038(8) N2 .0336(12) .0231(10) .0340(11) -.0015(9) .0073(9) -.0021(8) N3 .0328(12) .0414(13) .0331(11) -.0030(10) .0102(9) -.0026(9) O1 .0251(8) .0290(8) .0271(8) -.0017(7) -.0009(7) .0052(7) O2 .0308(11) .0630(13) .0716(14) -.0104(9) .0178(9) -.0103(11) O3 .0398(11) .0403(11) .0561(12) .0047(8) .0148(9) -.0079(9) C1 .0318(13) .0215(11) .0208(11) -.0027(9) .0028(9) .0022(8) C2 .0351(13) .0243(12) .0225(11) -.0023(10) .0089(9) .0003(9) C3 .0419(15) .0244(13) .0390(14) -.0098(11) .0158(11) -.0035(10) C4 .0351(15) .0368(14) .0377(14) -.0120(12) .0161(11) -.0040(11) C5 .0286(13) .0341(13) .0261(12) -.0030(10) .0097(9) -.0020(10) C6 .0320(13) .0223(12) .0234(11) -.0005(10) .0049(9) .0020(9) C7 .0234(12) .0200(11) .0271(12) .0023(9) .0047(9) -.0018(9) C8 .0259(13) .0288(13) .0365(14) -.0033(10) .0013(11) .0008(11) C9 .051(2) .0224(12) .0349(13) .0014(11) .0182(12) .0031(10) C10 .057(2) .039(2) .053(2) -.0073(15) .021(2) -.0167(14) C11 .058(2) .038(2) .036(2) .0202(14) .0077(14) .0054(13) N1' .0176(10) .0218(9) .0246(10) -.0008(8) -.0034(8) -.0016(8) N2' .0237(11) .0200(10) .0403(12) -.0019(9) .0080(9) -.0013(8) N3' .0242(11) .0303(11) .0454(12) .0003(9) .0076(9) .0047(9) O1' .0280(9) .0307(9) .0440(10) .0002(7) -.0062(7) -.0142(8) O2' .0291(10) .0453(11) .0820(15) .0043(9) .0221(10) -.0081(10) O3' .0318(10) .0307(10) .090(2) -.0086(8) .0152(10) -.0036(10) C1' .0226(11) .0209(10) .0195(10) .0012(9) .0017(8) .0006(9) C2' .0221(12) .0234(11) .0225(11) -.0032(9) .0030(9) -.0004(9) C3' .0284(13) .0186(12) .0360(13) -.0015(10) .0064(10) -.0028(10) C4' .0258(13) .0266(12) .0341(13) .0050(10) .0059(10) -.0012(10) C5' .0186(12) .0271(12) .0303(12) -.0018(9) .0047(9) .0005(9) C6' .0252(12) .0192(11) .0271(12) -.0032(9) .0027(9) .0009(9) C7' .0246(12) .0207(11) .0264(11) -.0033(9) .0010(9) -.0003(9) C8' .0282(14) .0289(14) .046(2) .0041(11) .0038(12) -.0058(12) C9' .0292(13) .0226(12) .0344(13) -.0057(10) .0110(10) -.0054(10) C10' .043(2) .0310(14) .045(2) -.0017(12) .0136(13) .0051(12) C11' .0297(14) .0307(14) .048(2) -.0090(11) .0151(12) -.0109(12) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_occupancy _atom_site_type_symbol N1 .73029(14) .33587(14) .98352(14) .0256(4) Uani d 1 N H1 .7799(19) .3186(17) 1.0331(18) .027(6) Uiso d 1 H N2 .7233(2) .12639(14) .95543(15) .0303(5) Uani d 1 N H2 .782(2) .161(2) .982(2) .045(8) Uiso d 1 H N3 .3650(2) .3359(2) .97602(15) .0354(5) Uani d 1 N O1 .68140(11) .42438(11) .83819(11) .0282(4) Uani d 1 O O2 .28318(14) .2890(2) .9614(2) .0541(5) Uani d 1 O O3 .37067(13) .42607(14) .99527(14) .0448(5) Uani d 1 O C1 .6366(2) .2821(2) .9748(2) .0252(5) Uani d 1 C C2 .6352(2) .1755(2) .9612(2) .0269(5) Uani d 1 C C3 .5409(2) .1259(2) .9523(2) .0341(6) Uani d 1 C H3 .5369(19) .054(2) .9429(19) .041(7) Uiso d 1 H C4 .4531(2) .1779(2) .9559(2) .0353(6) Uani d 1 C H4 .391(2) .1428(19) .9484(19) .040(7) Uiso d 1 H C5 .4574(2) .2815(2) .9709(2) .0291(5) Uani d 1 C C6 .5489(2) .3334(2) .9811(2) .0261(5) Uani d 1 C H6 .5518(17) .4019(19) .9906(17) .028(6) Uiso d 1 H C7 .7452(2) .4067(2) .9172(2) .0237(5) Uani d 1 C C8 .8444(2) .4633(2) .9453(2) .0313(5) Uani d 1 C H8A .873(2) .472(2) .886(2) .047(8) Uiso d 1 H H8B .830(2) .528(2) .972(2) .054(8) Uiso d 1 H H8C .895(2) .431(2) 1.000(2) .058(9) Uiso d 1 H C9 .7348(2) .0162(2) .9585(2) .0348(6) Uani d 1 C H9 .7076(18) -.0111(18) 1.0137(19) .035(7) Uiso d 1 H C10 .6813(3) -.0331(2) .8596(2) .0483(7) Uani d 1 C H10A .720(2) -.022(2) .809(2) .047(8) Uiso d 1 H H10B .611(3) -.008(3) .831(3) .083(12) Uiso d 1 H H10C .685(3) -.105(4) .875(3) .075(10) Uiso d 1 H C11 .8483(2) -.0093(2) .9827(2) .0446(7) Uani d 1 C H11A .859(3) -.081(3) .992(2) .076(10) Uiso d 1 H H11B .875(2) .011(2) .925(2) .044(7) Uiso d 1 H H11C .887(2) .024(2) 1.046(3) .062(9) Uiso d 1 H N1' .47907(14) .37470(13) .73534(14) .0226(4) Uani d 1 N H1' .5374(18) .3849(17) .7738(17) .021(6) Uiso d 1 H N2' .52413(15) .58013(14) .74652(15) .0279(4) Uani d 1 N H2' .572(2) .536(2) .7591(19) .041(8) Uiso d 1 H N3' .12761(15) .45403(15) .7528(2) .0334(5) Uani d 1 N O1' .38257(12) .26966(12) .62057(13) .0365(4) Uani d 1 O O2' .07007(13) .51303(14) .7835(2) .0506(5) Uani d 1 O O3' .10023(13) .36966(13) .7200(2) .0506(5) Uani d 1 O C1' .4019(2) .4456(2) .74413(15) .0215(5) Uani d 1 C C2' .4282(2) .5496(2) .75166(15) .0230(5) Uani d 1 C C3' .3515(2) .6192(2) .7607(2) .0278(5) Uani d 1 C H3' .3675(18) .6866(19) .7655(17) .030(6) Uiso d 1 H C4' .2543(2) .5879(2) .7630(2) .0290(5) Uani d 1 C H4' .2030(18) .6366(18) .7678(17) .029(6) Uiso d 1 H C5' .2305(2) .4870(2) .7531(2) .0255(5) Uani d 1 C C6' .3035(2) .4151(2) .7436(2) .0244(5) Uani d 1 C H6' .2856(17) .3452(19) .7363(17) .030(6) Uiso d 1 H C7' .4660(2) .2923(2) .6762(2) .0247(5) Uani d 1 C C8' .5595(2) .2291(2) .6804(2) .0350(6) Uani d 1 C H8D .574(3) .222(3) .616(3) .092(13) Uiso d 1 H H8E .619(3) .256(3) .727(3) .076(10) Uiso d 1 H H8F .549(3) .163(3) .697(3) .086(12) Uiso d 1 H C9' .5553(2) .6855(2) .7435(2) .0281(5) Uani d 1 C H9' .5303(16) .7212(16) .7959(16) .021(6) Uiso d 1 H C10' .5101(2) .7328(2) .6407(2) .0391(6) Uani d 1 C H10D .531(2) .806(2) .644(2) .048(8) Uiso d 1 H H10E .542(2) .700(2) .589(2) .053(8) Uiso d 1 H H10F .436(3) .729(2) .623(2) .067(10) Uiso d 1 H C11' .6717(2) .6896(2) .7682(2) .0351(6) Uani d 1 C H11D .696(2) .649(2) .719(2) .042(7) Uiso d 1 H H11E .702(2) .664(2) .837(2) .061(9) Uiso d 1 H H11F .696(2) .760(2) .764(2) .052(8) Uiso d 1 H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 _geom_angle_publ_flag C7 N1 C1 123.7(2) no C2 N2 C9 124.0(2) no O3 N3 O2 122.4(2) no O3 N3 C5 119.0(2) no O2 N3 C5 118.5(2) no C6 C1 C2 120.8(2) no C6 C1 N1 119.7(2) no C2 C1 N1 119.5(2) no N2 C2 C3 122.9(2) no N2 C2 C1 119.6(2) no C3 C2 C1 117.4(2) no C4 C3 C2 121.5(2) no C3 C4 C5 119.6(2) no C6 C5 C4 120.9(2) no C6 C5 N3 119.6(2) no C4 C5 N3 119.5(2) no C1 C6 C5 119.7(2) no O1 C7 N1 122.4(2) no O1 C7 C8 121.8(2) no N1 C7 C8 115.9(2) no N2 C9 C10 112.2(2) no N2 C9 C11 108.7(2) no C10 C9 C11 110.2(2) no C7' N1' C1' 126.1(2) no C2' N2' C9' 124.3(2) no O3' N3' O2' 122.8(2) no O3' N3' C5' 118.9(2) no O2' N3' C5' 118.4(2) no C6' C1' N1' 121.2(2) no C6' C1' C2' 120.5(2) no N1' C1' C2' 118.3(2) no N2' C2' C3' 121.7(2) no N2' C2' C1' 120.4(2) no C3' C2' C1' 117.9(2) no C4' C3' C2' 121.2(2) no C3' C4' C5' 119.5(2) no C4' C5' C6' 121.6(2) no C4' C5' N3' 119.6(2) no C6' C5' N3' 118.7(2) no C1' C6' C5' 119.3(2) no O1' C7' N1' 122.7(2) no O1' C7' C8' 121.4(2) no N1' C7' C8' 116.0(2) no N2' C9' C11' 108.3(2) no N2' C9' C10' 111.2(2) no C11' C9' C10' 111.3(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C7 1.348(3) no N1 C1 1.427(3) no N2 C2 1.367(3) no N2 C9 1.471(3) no N3 O3 1.224(3) no N3 O2 1.238(3) no N3 C5 1.449(3) no O1 C7 1.233(3) no C1 C6 1.378(3) no C1 C2 1.427(3) no C2 C3 1.406(3) no C3 C4 1.375(4) no C4 C5 1.390(3) no C5 C6 1.386(3) no C7 C8 1.501(3) no C9 C10 1.520(4) no C9 C11 1.520(4) no N1' C7' 1.345(3) no N1' C1' 1.424(3) no N2' C2' 1.365(3) no N2' C9' 1.463(3) no N3' O3' 1.231(3) no N3' O2' 1.236(3) no N3' C5' 1.447(3) no O1' C7' 1.237(3) no C1' C6' 1.378(3) no C1' C2' 1.424(3) no C2' C3' 1.409(3) no C3' C4' 1.374(3) no C4' C5' 1.377(3) no C5' C6' 1.394(3) no C7' C8' 1.499(3) no C9' C11' 1.520(3) no C9' C10' 1.526(4) no 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 _geom_hbond_publ_flag N1 H1 O1' 4_666 .86(2) 1.99(3) 2.806(3) 159(2) yes N2 H2 O1' 4_666 .92(3) 2.25(3) 3.054(3) 147(2) yes N1' H1' O1 . .85(2) 2.00(2) 2.834(3) 168(2) yes N2' H2' O1 . .85(3) 2.19(3) 3.014(3) 162(2) yes 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 _geom_torsion_publ_flag C7 N1 C1 C6 -63.7(3) no C7 N1 C1 C2 117.3(2) no C9 N2 C2 C3 -11.9(3) no C9 N2 C2 C1 169.5(2) no C6 C1 C2 N2 -179.8(2) no N1 C1 C2 N2 -.9(3) no C6 C1 C2 C3 1.5(3) no N1 C1 C2 C3 -179.6(2) no N2 C2 C3 C4 -178.3(2) no C1 C2 C3 C4 .4(3) no C2 C3 C4 C5 -1.5(4) no C3 C4 C5 C6 .8(4) no C3 C4 C5 N3 -179.2(2) no O3 N3 C5 C6 -4.3(3) no O2 N3 C5 C6 176.2(2) no O3 N3 C5 C4 175.7(2) no O2 N3 C5 C4 -3.8(3) no C2 C1 C6 C5 -2.2(3) no N1 C1 C6 C5 178.9(2) no C4 C5 C6 C1 1.0(3) no N3 C5 C6 C1 -179.0(2) no C1 N1 C7 O1 -6.6(3) no C1 N1 C7 C8 173.2(2) no C2 N2 C9 C10 75.2(3) no C2 N2 C9 C11 -162.7(2) no C7' N1' C1' C6' 38.3(3) no C7' N1' C1' C2' -140.6(2) no C9' N2' C2' C3' -3.9(3) no C9' N2' C2' C1' 173.7(2) no C6' C1' C2' N2' -176.4(2) no N1' C1' C2' N2' 2.5(3) no C6' C1' C2' C3' 1.4(3) no N1' C1' C2' C3' -179.7(2) no N2' C2' C3' C4' 178.2(2) no C1' C2' C3' C4' .5(3) no C2' C3' C4' C5' -2.1(3) no C3' C4' C5' C6' 1.9(3) no C3' C4' C5' N3' -178.4(2) no O3' N3' C5' C4' 162.6(2) no O2' N3' C5' C4' -15.7(3) no O3' N3' C5' C6' -17.8(3) no O2' N3' C5' C6' 163.9(2) no N1' C1' C6' C5' 179.6(2) no C2' C1' C6' C5' -1.5(3) no C4' C5' C6' C1' -.1(3) no N3' C5' C6' C1' -179.8(2) no C1' N1' C7' O1' .9(3) no C1' N1' C7' C8' -179.9(2) no C2' N2' C9' C11' 164.0(2) no C2' N2' C9' C10' -73.4(3) no