#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:48:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/21/2012120.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_2012120 loop_ _publ_author_name 'Borbulevych, Oleg Ya.' 'Golding, Igor R.' 'Shchegolikhin, Alexander N.' 'Klemenkova, Zinaida S.' 'Antipin, Mikhail Yu.' _publ_section_title ; Conformational polymorphs of 22-cyano-N-methyl-5-phenylpent-2-en-4-ynamide ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 996 _journal_page_last 998 _journal_paper_doi 10.1107/S010827010100909X _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C13 H10 N2 O' _chemical_formula_sum 'C13 H10 N2 O' _chemical_formula_weight 210.23 _chemical_melting_point 384 _chemical_name_systematic ; 2-cyano-5-phenyl-pent-2-en-4-ynoic acid N-methylamide form (II) ; _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' _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 97.29(4) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 22.652(12) _cell_length_b 9.728(7) _cell_length_c 10.269(5) _cell_measurement_reflns_used 24 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 11 _cell_measurement_theta_min 10 _cell_volume 2245(2) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'CAD-4 Software' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .981 _diffrn_measured_fraction_theta_max .981 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _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 .079 _diffrn_reflns_av_sigmaI/netI .074 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4929 _diffrn_reflns_theta_full 27.01 _diffrn_reflns_theta_max 27.01 _diffrn_reflns_theta_min 1.81 _diffrn_standards_decay_% 3.4 _diffrn_standards_interval_count 90 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu .081 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 880 _exptl_crystal_size_max .5 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .2 _refine_diff_density_max .16 _refine_diff_density_min -.22 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .959 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 291 _refine_ls_number_reflns 4810 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .959 _refine_ls_R_factor_all .165 _refine_ls_R_factor_gt .052 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.091P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .169 _reflns_number_gt 2134 _reflns_number_total 4810 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bm1452.cif _cod_data_source_block II _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_enum 1527 2010-12-29 10:47:43Z saulius 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_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2012120 _cod_database_fobs_code 2012120 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 O1 .51989(9) .1326(2) .65637(18) .0714(6) Uani d . 1 . . O N1 .40660(13) .5274(3) .5243(3) .0824(8) Uani d . 1 . . N N2 .52030(9) .3542(2) .72239(19) .0545(6) Uani d . 1 . . N H2 .5022 .4320 .7122 .065 Uiso calc R 1 . . H C1 .50077(11) .2491(3) .6456(2) .0490(6) Uani d . 1 . . C C2 .45142(11) .2854(3) .5377(2) .0476(6) Uani d . 1 . . C C3 .43153(11) .1924(3) .4453(2) .0555(7) Uani d . 1 . . C H3 .4479 .1046 .4507 .067 Uiso calc R 1 . . H C4 .38672(12) .2227(3) .3404(2) .0536(7) Uani d . 1 . . C C5 .34816(12) .2549(3) .2550(2) .0519(7) Uani d . 1 . . C C6 .42675(12) .4201(3) .5295(2) .0558(7) Uani d . 1 . . C C7 .30001(11) .2962(3) .1603(2) .0462(6) Uani d . 1 . . C C8 .27396(13) .4228(3) .1721(3) .0664(8) Uani d . 1 . . C H8 .2894 .4825 .2387 .080 Uiso calc R 1 . . H C9 .22506(14) .4615(4) .0858(3) .0778(9) Uani d . 1 . . C H9 .2074 .5468 .0946 .093 Uiso calc R 1 . . H C10 .20243(13) .3740(4) -.0132(3) .0694(9) Uani d . 1 . . C H10 .1689 .3994 -.0701 .083 Uiso calc R 1 . . H C11 .22856(13) .2512(3) -.0285(3) .0632(8) Uani d . 1 . . C H11 .2138 .1939 -.0975 .076 Uiso calc R 1 . . H C12 .27716(12) .2101(3) .0581(2) .0546(7) Uani d . 1 . . C H12 .2946 .1248 .0479 .066 Uiso calc R 1 . . H C13 .57174(12) .3410(3) .8237(3) .0679(8) Uani d . 1 . . C H13A .5790 .2455 .8432 .102 Uiso calc R 1 . . H H13B .5637 .3880 .9018 .102 Uiso calc R 1 . . H H13C .6061 .3807 .7926 .102 Uiso calc R 1 . . H O1' 1.01898(9) .7563(2) .68323(15) .0689(6) Uani d . 1 . . O N1' .89839(14) .6122(4) .3035(3) .1193(14) Uani d . 1 . . N N2' 1.01957(9) .7867(2) .46670(17) .0479(5) Uani d . 1 . . N H2' 1.0037 .7650 .3889 .058 Uiso calc R 1 . . H C1' .99860(11) .7301(3) .5693(2) .0446(6) Uani d . 1 . . C C2' .94784(10) .6320(3) .5402(2) .0455(6) Uani d . 1 . . C C3' .92944(12) .5580(3) .6369(2) .0576(7) Uani d . 1 . . C H3' .9508 .5691 .7197 .069 Uiso calc R 1 . . H C4' .88133(13) .4649(3) .6277(3) .0581(7) Uani d . 1 . . C C5' .84124(13) .3868(3) .6332(3) .0554(7) Uani d . 1 . . C C6' .91935(13) .6196(3) .4093(3) .0668(8) Uani d . 1 . . C C7' .79511(11) .2901(3) .6496(2) .0478(6) Uani d . 1 . . C C8' .73735(12) .3048(3) .5861(3) .0588(7) Uani d . 1 . . C H8' .7283 .3764 .5269 .071 Uiso calc R 1 . . H C9' .69395(13) .2145(3) .6104(3) .0719(9) Uani d . 1 . . C H9' .6554 .2252 .5684 .086 Uiso calc R 1 . . H C10' .70703(14) .1083(3) .6964(3) .0733(9) Uani d . 1 . . C H10' .6772 .0480 .7139 .088 Uiso calc R 1 . . H C11' .76401(14) .0903(3) .7570(3) .0699(8) Uani d . 1 . . C H11' .7730 .0158 .8129 .084 Uiso calc R 1 . . H C12' .80749(12) .1811(3) .7356(3) .0570(7) Uani d . 1 . . C H12' .8458 .1699 .7790 .068 Uiso calc R 1 . . H C13' 1.06840(12) .8841(3) .4823(3) .0603(7) Uani d . 1 . . C H13D 1.0622 .9495 .5493 .091 Uiso calc R 1 . . H H13E 1.0702 .9314 .4009 .091 Uiso calc R 1 . . H H13F 1.1051 .8360 .5072 .091 Uiso calc R 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 O1 .0835(14) .0633(13) .0603(12) .0207(11) -.0185(10) -.0021(10) N1 .100(2) .0637(18) .0753(18) .0127(16) -.0191(15) .0025(15) N2 .0523(13) .0602(14) .0472(12) .0020(11) -.0079(9) .0056(11) C1 .0486(14) .0600(18) .0372(12) .0031(13) .0012(10) .0035(13) C2 .0491(14) .0542(16) .0384(12) .0015(13) .0015(10) .0068(12) C3 .0577(16) .0655(18) .0417(13) .0068(14) .0001(12) .0023(13) C4 .0570(16) .0620(17) .0410(13) -.0002(14) .0029(12) -.0055(13) C5 .0538(15) .0637(18) .0374(12) .0016(13) .0034(12) .0001(12) C6 .0575(17) .0609(19) .0457(14) -.0014(15) -.0059(12) .0058(14) C7 .0517(14) .0537(16) .0332(12) -.0066(13) .0053(10) .0003(11) C8 .082(2) .067(2) .0463(15) .0068(17) -.0049(14) -.0102(14) C9 .085(2) .076(2) .0685(19) .0271(18) -.0049(17) .0016(18) C10 .0617(19) .094(3) .0497(16) .0131(18) -.0034(13) .0090(17) C11 .0592(17) .085(2) .0429(14) -.0154(16) -.0048(12) -.0057(15) C12 .0585(16) .0569(17) .0477(14) -.0055(14) .0040(12) -.0053(13) C13 .0569(17) .086(2) .0557(16) -.0011(16) -.0146(13) -.0020(15) O1' .0752(13) .1020(16) .0283(8) -.0310(11) .0014(8) -.0067(9) N1' .115(3) .183(4) .0527(16) -.072(2) -.0178(16) .000(2) N2' .0511(12) .0631(14) .0287(9) -.0101(11) .0017(8) -.0056(10) C1' .0490(14) .0551(16) .0294(11) -.0039(12) .0033(10) -.0067(11) C2' .0435(13) .0585(16) .0335(12) -.0036(12) .0013(10) -.0055(12) C3' .0564(16) .0710(19) .0436(14) -.0109(15) -.0010(12) .0047(14) C4' .0615(18) .0609(18) .0516(15) -.0017(16) .0055(13) .0070(13) C5' .0578(17) .0577(17) .0514(15) .0018(15) .0097(12) .0058(13) C6' .0627(18) .089(2) .0461(15) -.0277(16) -.0028(13) -.0014(15) C7' .0516(15) .0491(15) .0432(13) .0015(12) .0088(11) -.0003(12) C8' .0647(18) .0573(17) .0514(15) .0020(15) -.0036(13) .0037(13) C9' .0526(17) .086(2) .074(2) -.0091(17) -.0054(14) -.0035(19) C10' .070(2) .072(2) .081(2) -.0176(17) .0198(17) .0017(18) C11' .075(2) .069(2) .0672(18) -.0007(17) .0146(16) .0179(16) C12' .0596(17) .0593(17) .0515(15) .0030(14) .0046(12) .0060(13) C13' .0591(17) .073(2) .0506(14) -.0145(15) .0117(13) -.0041(14) 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 C1 N2 C13 121.8(2) no O1 C1 N2 125.1(2) no O1 C1 C2 120.4(2) no N2 C1 C2 114.5(2) no C3 C2 C6 118.9(2) no C3 C2 C1 120.7(2) no C6 C2 C1 120.4(2) no C2 C3 C4 122.7(3) no C5 C4 C3 176.4(3) no C4 C5 C7 176.1(3) no N1 C6 C2 179.1(3) no C8 C7 C12 118.9(2) no C8 C7 C5 119.4(2) no C12 C7 C5 121.7(2) no C7 C8 C9 120.3(3) no C10 C9 C8 120.0(3) no C11 C10 C9 120.4(3) no C10 C11 C12 120.4(3) no C11 C12 C7 120.0(3) no C1' N2' C13' 121.8(2) no O1' C1' N2' 122.7(2) no O1' C1' C2' 120.7(2) no N2' C1' C2' 116.7(2) no C3' C2' C6' 120.7(2) no C3' C2' C1' 120.0(2) no C6' C2' C1' 119.3(2) no C2' C3' C4' 127.5(2) no C5' C4' C3' 173.5(3) no C4' C5' C7' 175.7(3) no N1' C6' C2' 177.4(3) no C12' C7' C8' 118.6(3) no C12' C7' C5' 119.1(2) no C8' C7' C5' 122.2(2) no C9' C8' C7' 120.2(3) no C8' C9' C10' 120.2(3) no C9' C10' C11' 120.3(3) no C12' C11' C10' 120.1(3) no C11' C12' C7' 120.5(3) no C1 N2 H2 119.1 no C13 N2 H2 119.1 no C2 C3 H3 118.6 no C4 C3 H3 118.6 no C7 C8 H8 119.8 no C9 C8 H8 119.8 no C10 C9 H9 120.0 no C8 C9 H9 120.0 no C11 C10 H10 119.8 no C9 C10 H10 119.8 no C10 C11 H11 119.8 no C12 C11 H11 119.8 no C11 C12 H12 120.0 no C7 C12 H12 120.0 no N2 C13 H13A 109.5 no N2 C13 H13B 109.5 no N2 C13 H13C 109.5 no H13A C13 H13B 109.5 no H13A C13 H13C 109.5 no H13B C13 H13C 109.5 no C1' N2' H2' 119.1 no C13' N2' H2' 119.1 no C2' C3' H3' 116.3 no C4' C3' H3' 116.3 no C9' C8' H8' 119.9 no C7' C8' H8' 119.9 no C8' C9' H9' 119.9 no C10' C9' H9' 119.9 no C9' C10' H10' 119.8 no C11' C10' H10' 119.8 no C12' C11' H11' 119.9 no C10' C11' H11' 119.9 no C11' C12' H12' 119.7 no C7' C12' H12' 119.7 no N2' C13' H13D 109.5 no N2' C13' H13E 109.5 no N2' C13' H13F 109.5 no H13D C13' H13E 109.5 no H13D C13' H13F 109.5 no H13E C13' H13F 109.5 no 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 C1 . 1.213(3) yes N1 C6 . 1.138(4) yes N2 C1 . 1.332(3) yes N2 C13 . 1.466(3) yes C1 C2 . 1.513(3) yes C2 C3 . 1.346(4) yes C2 C6 . 1.423(4) yes C3 C4 . 1.414(4) yes C4 C5 . 1.199(3) yes C5 C7 . 1.424(4) yes C7 C8 . 1.378(4) no C7 C12 . 1.391(3) no C8 C9 . 1.381(4) no C9 C10 . 1.375(4) no C10 C11 . 1.351(4) no C11 C12 . 1.383(4) no O1' C1' . 1.228(3) yes N1' C6' . 1.131(3) yes N2' C1' . 1.329(3) yes N2' C13' . 1.450(3) yes C1' C2' . 1.495(3) yes C2' C3' . 1.335(3) yes C2' C6' . 1.420(3) yes C3' C4' . 1.411(4) yes C4' C5' . 1.191(4) yes C5' C7' . 1.432(4) yes C7' C12' . 1.385(4) no C7' C8' . 1.393(4) no C8' C9' . 1.365(4) no C9' C10' . 1.366(4) no C10' C11' . 1.371(4) no C11' C12' . 1.362(4) no N2 H2 . .8600 no C3 H3 . .9300 no C8 H8 . .9300 no C9 H9 . .9300 no C10 H10 . .9300 no C11 H11 . .9300 no C12 H12 . .9300 no C13 H13A . .9600 no C13 H13B . .9600 no C13 H13C . .9600 no N2' H2' . .8600 no C3' H3' . .9300 no C8' H8' . .9300 no C9' H9' . .9300 no C10' H10' . .9300 no C11' H11' . .9300 no C12' H12' . .9300 no C13' H13D . .9600 no C13' H13E . .9600 no C13' H13F . .9600 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag C6 H2 2.38 yes O1' H3' 2.45 yes C6' H2' 2.41 yes 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 N2 H2 O1 2_656 .86 2.46 3.163(4) 139.3 yes N2' H2' O1' 4_575 .86 2.19 2.939(3) 145.1 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 C13 N2 C1 O1 5.3(4) no C13 N2 C1 C2 -174.0(2) no O1 C1 C2 C3 -5.8(4) no N2 C1 C2 C3 173.5(2) no O1 C1 C2 C6 176.5(3) no N2 C1 C2 C6 -4.2(3) no C6 C2 C3 C4 -.4(4) no C1 C2 C3 C4 -178.2(2) no C12 C7 C8 C9 1.6(4) no C5 C7 C8 C9 -176.3(3) no C7 C8 C9 C10 -.5(5) no C8 C9 C10 C11 -1.4(5) no C9 C10 C11 C12 2.2(5) no C10 C11 C12 C7 -1.0(4) no C8 C7 C12 C11 -.9(4) no C5 C7 C12 C11 176.9(2) no C13' N2' C1' O1' .1(4) no C13' N2' C1' C2' 179.6(2) no O1' C1' C2' C3' -9.1(4) no N2' C1' C2' C3' 171.5(2) no O1' C1' C2' C6' 170.4(3) no N2' C1' C2' C6' -9.1(4) no C6' C2' C3' C4' -1.8(5) no C1' C2' C3' C4' 177.7(3) no C12' C7' C8' C9' 1.1(4) no C5' C7' C8' C9' -176.2(3) no C7' C8' C9' C10' -.6(5) no C8' C9' C10' C11' -1.2(5) no C9' C10' C11' C12' 2.4(5) no C10' C11' C12' C7' -1.9(4) no C8' C7' C12' C11' .2(4) no C5' C7' C12' C11' 177.5(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21182078