#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/82/2008284.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_2008284 loop_ _publ_author_name 'S. Selladurai' 'R. Chandrasekaran' 'L. Govindasamy' 'P. Murugan' 'V. T. Ramakrishnan' _publ_section_title ; 2-[3-(Pyrrolidin-1-yl)cyclohex-2-en-1-ylidene]propanedinitrile ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 401 _journal_page_last 403 _journal_paper_doi 10.1107/S0108270198009627 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C13 H15 N3' _chemical_formula_weight 213.28 _chemical_melting_point 225 _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 90.0 _cell_angle_beta 92.20(3) _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 7.1180(10) _cell_length_b 20.8940(10) _cell_length_c 7.768(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 11 _cell_measurement_theta_min 5 _cell_volume 1154.4(3) _computing_cell_refinement SDP _computing_data_collection 'SDP (Frenz, 1989)' _computing_data_reduction SDP _computing_molecular_graphics ZORTEP _computing_publication_material 'SHELXL93, PARST (Nardelli, 1995)' _computing_structure_refinement SHELXL93 _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 2507 _diffrn_reflns_theta_max 75.53 _diffrn_reflns_theta_min 4.23 _diffrn_standards_decay_% <0.5 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 3600 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.588 _exptl_absorpt_correction_type none _exptl_crystal_colour Orange _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_description parallelepiped _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.42 _refine_diff_density_max 0.256 _refine_diff_density_min -0.388 _refine_ls_extinction_coef 0.0258(3) _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1993)' _refine_ls_goodness_of_fit_all 0.994 _refine_ls_goodness_of_fit_obs 1.013 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 2330 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.073 _refine_ls_restrained_S_obs 1.013 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_obs 0.0590 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.4176P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1881 _refine_ls_wR_factor_obs 0.1720 _reflns_number_observed 2193 _reflns_number_total 2341 _reflns_observed_criterion >2sigma(I) _cod_data_source_file os1029.cif _cod_data_source_block pyrr22 _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.4176P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.4176P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2008284 _cod_database_fobs_code 2008284 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 0.0586(11) 0.0682(11) 0.0881(14) 0.0094(8) 0.0001(9) 0.0028(9) N2 0.0944(15) 0.0570(11) 0.0803(13) -0.0180(10) 0.0034(11) -0.0175(9) N3 0.0448(8) 0.0398(7) 0.0459(8) 0.0002(5) -0.0014(5) -0.0021(5) C1 0.0423(8) 0.0434(8) 0.0345(8) -0.0045(6) 0.0041(6) 0.0018(6) C2 0.0363(7) 0.0433(8) 0.0403(8) -0.0006(6) -0.0022(6) 0.0001(6) C3 0.0409(8) 0.0428(8) 0.0341(8) -0.0006(6) 0.0002(6) 0.0014(6) C4 0.0434(9) 0.0548(10) 0.0560(10) 0.0073(7) -0.0059(7) -0.0052(8) C5 0.0363(8) 0.0681(12) 0.0597(11) -0.0020(7) -0.0015(7) -0.0100(9) C6 0.0424(9) 0.0552(10) 0.0448(9) -0.0072(7) -0.0012(7) -0.0053(7) C7 0.0508(9) 0.0421(8) 0.0418(9) -0.0049(6) 0.0058(7) -0.0004(6) C8 0.0575(11) 0.0416(9) 0.0531(10) 0.0018(7) 0.0075(8) 0.0012(7) C9 0.0645(11) 0.0451(9) 0.0516(10) -0.0063(8) 0.0084(8) -0.0020(7) C10 0.0717(13) 0.0399(9) 0.0668(12) 0.0071(8) -0.0042(9) -0.0047(8) C11 0.097(2) 0.0467(13) 0.187(4) -0.0049(12) -0.032(2) -0.023(2) C12 0.074(2) 0.068(2) 0.181(3) -0.0168(13) -0.006(2) -0.049(2) C13 0.0453(9) 0.0535(10) 0.0654(12) -0.0066(7) -0.0034(8) -0.0084(8) 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_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol N1 -0.3552(3) 0.60232(9) 0.6940(3) 0.0717(5) Uani d . 1 . N N2 0.1498(3) 0.67533(9) 0.9657(3) 0.0772(6) Uani d . 1 . N N3 -0.0324(2) 0.36130(6) 0.6287(2) 0.0436(4) Uani d . 1 . N C1 0.0705(2) 0.52269(7) 0.7863(2) 0.0400(4) Uani d . 1 . C C2 -0.0220(2) 0.47115(7) 0.7079(2) 0.0401(4) Uani d . 1 . C H2 -0.1449(2) 0.47673(7) 0.6657(2) 0.048 Uiso calc R 1 . H C3 0.0624(2) 0.41144(7) 0.6901(2) 0.0393(4) Uani d . 1 . C C4 0.2653(2) 0.40208(9) 0.7442(3) 0.0516(5) Uani d . 1 . C H4A 0.3238(2) 0.37387(9) 0.6628(3) 0.062 Uiso calc R 1 . H H4B 0.2729(2) 0.38164(9) 0.8564(3) 0.062 Uiso calc R 1 . H C5 0.3720(2) 0.46493(10) 0.7532(3) 0.0548(5) Uani d . 1 . C H5A 0.4957(2) 0.45782(10) 0.8064(3) 0.066 Uiso calc R 1 . H H5B 0.3883(2) 0.48084(10) 0.6374(3) 0.066 Uiso calc R 1 . H C6 0.2687(2) 0.51445(9) 0.8557(2) 0.0476(4) Uani d . 1 . C H6A 0.2674(2) 0.50125(9) 0.9753(2) 0.057 Uiso calc R 1 . H H6B 0.3343(2) 0.55506(9) 0.8507(2) 0.057 Uiso calc R 1 . H C7 -0.0164(2) 0.58220(8) 0.8079(2) 0.0448(4) Uani d . 1 . C C8 -0.2044(3) 0.59362(8) 0.7454(2) 0.0506(4) Uani d . 1 . C C9 0.0762(3) 0.63358(9) 0.8948(2) 0.0536(5) Uani d . 1 . C C10 0.0458(3) 0.29645(9) 0.6092(3) 0.0596(5) Uani d . 1 . C H10A 0.0925(3) 0.27971(9) 0.7192(3) 0.072 Uiso calc R 1 . H H10B 0.1472(3) 0.29644(9) 0.5292(3) 0.072 Uiso calc R 1 . H C11 -0.1179(4) 0.25822(12) 0.5402(6) 0.1111(13) Uani d . 1 . C H11A -0.1000(4) 0.24756(12) 0.4204(6) 0.133 Uiso calc R 1 . H H11B -0.1269(4) 0.21862(12) 0.6045(6) 0.133 Uiso calc R 1 . H C12 -0.2837(4) 0.29351(13) 0.5541(6) 0.1081(12) Uani d . 1 . C H12A -0.3559(4) 0.27667(13) 0.6473(6) 0.130 Uiso calc R 1 . H H12B -0.3596(4) 0.29003(13) 0.4481(6) 0.130 Uiso calc R 1 . H C13 -0.2358(3) 0.36199(9) 0.5883(3) 0.0549(5) Uani d . 1 . C H13A -0.2651(3) 0.38819(9) 0.4877(3) 0.066 Uiso calc R 1 . H H13B -0.3040(3) 0.37834(9) 0.6846(3) 0.066 Uiso calc R 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 0.0181 0.0091 '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 0.0311 0.0180 '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 C3 N3 C13 123.57(14) yes C3 N3 C10 125.03(15) yes C13 N3 C10 111.11(14) yes C2 C1 C7 122.41(15) ? C2 C1 C6 119.41(14) ? C7 C1 C6 118.15(14) ? C1 C2 C3 122.57(14) ? C1 C2 H2 118.71(9) ? C3 C2 H2 118.71(9) ? N3 C3 C2 121.88(14) yes N3 C3 C4 117.97(14) yes C2 C3 C4 120.14(14) ? C3 C4 C5 112.00(14) ? C3 C4 H4A 109.21(9) ? C5 C4 H4A 109.21(10) ? C3 C4 H4B 109.21(10) ? C5 C4 H4B 109.21(11) ? H4A C4 H4B 107.9 ? C6 C5 C4 111.32(15) ? C6 C5 H5A 109.37(9) ? C4 C5 H5A 109.37(10) ? C6 C5 H5B 109.37(11) ? C4 C5 H5B 109.37(11) ? H5A C5 H5B 108.0 ? C1 C6 C5 111.01(13) ? C1 C6 H6A 109.43(9) ? C5 C6 H6A 109.43(11) ? C1 C6 H6B 109.43(9) ? C5 C6 H6B 109.43(10) ? H6A C6 H6B 108.0 ? C1 C7 C9 122.0(2) ? C1 C7 C8 121.34(15) ? C9 C7 C8 116.7(2) ? N1 C8 C7 179.3(2) yes N2 C9 C7 179.4(2) yes N3 C10 C11 103.6(2) yes N3 C10 H10A 111.04(10) ? C11 C10 H10A 111.0(2) ? N3 C10 H10B 111.04(10) ? C11 C10 H10B 111.0(2) ? H10A C10 H10B 109.0 ? C12 C11 C10 109.8(2) ? C12 C11 H11A 109.7(3) ? C10 C11 H11A 109.7(2) ? C12 C11 H11B 109.7(2) ? C10 C11 H11B 109.7(2) ? H11A C11 H11B 108.2 ? C11 C12 C13 109.3(2) ? C11 C12 H12A 109.8(3) ? C13 C12 H12A 109.8(2) ? C11 C12 H12B 109.8(2) ? C13 C12 H12B 109.8(2) ? H12A C12 H12B 108.3 ? N3 C13 C12 104.2(2) yes N3 C13 H13A 110.92(10) ? C12 C13 H13A 110.9(2) ? N3 C13 H13B 110.92(10) ? C12 C13 H13B 110.9(2) ? H13A C13 H13B 108.9 ? 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 N1 C8 . 1.146(3) yes N2 C9 . 1.147(3) yes N3 C3 . 1.325(2) ? N3 C13 . 1.469(2) yes N3 C10 . 1.475(2) yes C1 C2 . 1.390(2) yes C1 C7 . 1.401(2) yes C1 C6 . 1.501(2) yes C2 C3 . 1.394(2) yes C2 H2 . 0.93 ? C3 C4 . 1.501(2) yes C4 C5 . 1.517(3) yes C4 H4A . 0.97 ? C4 H4B . 0.97 ? C5 C6 . 1.513(2) yes C5 H5A . 0.97 ? C5 H5B . 0.97 ? C6 H6A . 0.97 ? C6 H6B . 0.97 ? C7 C9 . 1.417(2) yes C7 C8 . 1.426(3) yes C10 C11 . 1.495(3) yes C10 H10A . 0.97 ? C10 H10B . 0.97 ? C11 C12 . 1.399(4) yes C11 H11A . 0.97 ? C11 H11B . 0.97 ? C12 C13 . 1.493(3) yes C12 H12A . 0.97 ? C12 H12B . 0.97 ? C13 H13A . 0.97 ? C13 H13B . 0.97 ? 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 C1 C2 C3 -178.36(14) ? C6 C1 C2 C3 -0.2(2) ? C13 N3 C3 C2 -5.5(2) ? C10 N3 C3 C2 -178.7(2) yes C13 N3 C3 C4 173.3(2) yes C10 N3 C3 C4 0.1(2) ? C1 C2 C3 N3 174.04(15) yes C1 C2 C3 C4 -4.7(2) ? N3 C3 C4 C5 160.57(15) yes C2 C3 C4 C5 -20.6(2) ? C3 C4 C5 C6 49.6(2) ? C2 C1 C6 C5 29.9(2) ? C7 C1 C6 C5 -151.9(2) ? C4 C5 C6 C1 -54.1(2) ? C2 C1 C7 C9 177.1(2) yes C6 C1 C7 C9 -1.1(2) yes C2 C1 C7 C8 -1.8(2) yes C6 C1 C7 C8 179.9(15) yes C1 C7 C8 N1 -25.7(17) yes C9 C7 C8 N1 155.3(16) ? C1 C7 C9 N2 -145.5(2) yes C8 C7 C9 N2 33.5(2) ? C3 N3 C10 C11 178.5(2) ? C13 N3 C10 C11 4.6(3) ? N3 C10 C11 C12 -11.9(4) ? C10 C11 C12 C13 14.9(5) yes C3 N3 C13 C12 -170.3(2) ? C10 N3 C13 C12 3.7(3) ? C11 C12 C13 N3 -11.4(4) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21105672 2 PubChem 100966250