#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:08:28 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201955 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/73/2007329.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_2007329 loop_ _publ_author_name 'Elgemeie, Galal E. H.' 'Hanfy, Nadia' 'Hopf, Henning' 'Jones, Peter G.' _publ_section_title ; 2-Dicyanomethylene-5,6-dimethyl-1,2-dihydropyridine-3-carbonitrile ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 820 _journal_page_last 822 _journal_paper_doi 10.1107/S0108270197019835 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C11 H8 N4' _chemical_formula_sum 'C11 H8 N4' _chemical_formula_weight 196.21 _chemical_name_systematic ; 2-Dicyanomethylene-5,6-dimethyl-3-cyano-1,2-dihydropyridine ; _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 106.11(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.712(3) _cell_length_b 11.579(4) _cell_length_c 11.416(4) _cell_measurement_reflns_used 48 _cell_measurement_temperature 143(2) _cell_measurement_theta_max 11.5 _cell_measurement_theta_min 10.0 _cell_volume 979.4(6) _computing_cell_refinement DIF4 _computing_data_collection 'DIF4 (Stoe & Cie, 1992a)' _computing_data_reduction 'REDU4 (Stoe & Cie, 1992b)' _computing_molecular_graphics 'XP (Siemens, 1994)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 143(2) _diffrn_measurement_device 'Stoe Stadi-4' _diffrn_measurement_method \w/\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.053 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 2432 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 3.26 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_meas ? _exptl_crystal_description needle _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.232 _refine_diff_density_min -0.199 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.018 _refine_ls_goodness_of_fit_obs 1.084 _refine_ls_hydrogen_treatment 'H atoms treated by a mixture of independent and constrained refinement' _refine_ls_matrix_type full _refine_ls_number_parameters 142 _refine_ls_number_reflns 1726 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.018 _refine_ls_restrained_S_obs 1.084 _refine_ls_R_factor_all 0.090 _refine_ls_R_factor_obs .054 _refine_ls_shift/esd_max 0.006 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0553P)^2^+0.5865P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.143 _refine_ls_wR_factor_obs .123 _reflns_number_observed 1163 _reflns_number_total 1726 _reflns_observed_criterion I>2\s(I) _cod_data_source_file fg1411.cif _cod_data_source_block eggy _cod_depositor_comments ; 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 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0553P)^2^+0.5865P] 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^)+(0.0553P)^2^+0.5865P] 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 2007329 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 .0174(11) .0362(14) .0304(12) .0007(10) .0086(10) .0006(11) N2 .0346(13) .0579(18) .0538(17) -.0087(13) .0229(13) -.0088(14) N3 .0350(14) .0614(19) .0505(16) -.0099(14) .0199(13) -.0238(15) N4 .0470(16) .059(2) .0550(17) -.0192(15) .0224(14) -.0132(16) C1 .0187(12) .0295(15) .0251(13) .0015(11) .0048(10) .0034(12) C2 .0219(12) .0341(16) .0250(13) -.0007(12) .0059(11) .0026(12) C3 .0220(12) .0404(17) .0260(14) .0016(13) .0087(11) .0059(13) C4 .0273(13) .0393(17) .0233(13) .0043(13) .0082(11) .0057(13) C5 .0272(14) .0339(16) .0235(13) .0020(12) .0075(11) .0019(12) C6 .0226(13) .0334(16) .0300(14) .0020(12) .0095(11) -.0004(13) C7 .0276(14) .0380(18) .0318(15) .0012(13) .0120(12) -.0008(13) C8 .0242(13) .0411(18) .0390(16) .0009(13) .0166(12) -.0023(15) C9 .0259(14) .0434(19) .0338(15) -.0011(14) .0141(12) .0031(15) C10 .0398(16) .047(2) .0352(16) .0022(15) .0165(14) -.0011(15) C11 .0363(16) .0432(19) .0362(16) -.0060(14) .0130(13) -.0071(15) 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 .7161(3) .4441(2) .6188(2) .0276(6) Uani d . 1 . N H1 .1820(4) .468(3) .610(3) .038(8) Uiso d . 1 . H N2 1.0035(3) .3888(3) .4350(2) .0466(7) Uani d . 1 . N N3 .5559(3) .1614(3) .2947(2) .0473(7) Uani d . 1 . N N4 .2811(4) .1438(3) .4710(3) .0519(8) Uani d . 1 . N C1 .6292(3) .3551(2) .5478(2) .0247(6) Uani d . 1 . C C2 .4654(3) .3209(2) .5712(2) .0271(6) Uani d . 1 . C C3 .4035(3) .3793(2) .6577(2) .0291(7) Uani d . 1 . C H3 .2915 .3566 .6699 .035 Uiso calc R 1 . H C4 .4973(3) .4693(3) .7271(2) .0297(7) Uani d . 1 . C C5 .6610(3) .4993(2) .7078(2) .0281(6) Uani d . 1 . C C6 .7065(3) .3070(2) .4610(2) .0282(6) Uani d . 1 . C C7 .8715(4) .3506(3) .4471(2) .0317(7) Uani d . 1 . C C8 .6196(3) .2249(3) .3718(3) .0332(7) Uani d . 1 . C C9 .3644(4) .2232(3) .5120(3) .0332(7) Uani d . 1 . C C10 .4301(4) .5282(3) .8235(3) .0395(8) Uani d . 1 . C H10A .5053 .5056 .9043 .047 Uiso calc R 1 . H H10B .3048 .5053 .8147 .047 Uiso calc R 1 . H H10C .4362 .6121 .8141 .047 Uiso calc R 1 . H C11 .7844(4) .5885(3) .7792(3) .0380(7) Uani d . 1 . C H11A .8921 .5942 .7499 .046 Uiso calc R 1 . H H11B .8199 .5670 .8656 .046 Uiso calc R 1 . H H11C .7224 .6633 .7692 .046 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 0.0033 0.0016 '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 0.0061 0.0033 '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 C5 N1 C1 126.3(2) y N1 C1 C6 118.9(2) ? N1 C1 C2 114.5(2) y C6 C1 C2 126.6(2) ? C3 C2 C1 119.9(2) y C3 C2 C9 118.2(2) ? C1 C2 C9 121.9(2) ? C4 C3 C2 123.1(2) y C5 C4 C3 116.9(2) y C5 C4 C10 121.1(3) ? C3 C4 C10 121.9(2) ? N1 C5 C4 119.1(3) y N1 C5 C11 116.8(2) ? C4 C5 C11 124.1(2) ? C1 C6 C7 120.5(2) ? C1 C6 C8 124.3(2) ? C7 C6 C8 114.7(2) ? N2 C7 C6 178.2(3) ? N3 C8 C6 175.4(3) ? N4 C9 C2 176.0(3) ? 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 C5 . 1.364(3) y N1 C1 . 1.367(3) y N2 C7 . 1.154(3) ? N3 C8 . 1.147(4) ? N4 C9 . 1.144(4) ? C1 C6 . 1.405(4) y C1 C2 . 1.418(3) y C2 C3 . 1.387(4) y C2 C9 . 1.432(4) ? C3 C4 . 1.385(4) y C4 C5 . 1.385(4) y C4 C10 . 1.504(4) ? C5 C11 . 1.486(4) ? C6 C7 . 1.418(4) ? C6 C8 . 1.418(4) ? 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 C5 N1 C1 C6 -179.2(3) C5 N1 C1 C2 0.9(4) N1 C1 C2 C3 1.9(4) C6 C1 C2 C3 -178.0(3) N1 C1 C2 C9 -175.0(2) C6 C1 C2 C9 5.2(4) C1 C2 C3 C4 -2.0(4) C9 C2 C3 C4 174.9(3) C2 C3 C4 C5 -0.7(4) C2 C3 C4 C10 -177.8(3) C1 N1 C5 C4 -3.7(4) C1 N1 C5 C11 175.8(2) C3 C4 C5 N1 3.3(4) C10 C4 C5 N1 -179.5(2) C3 C4 C5 C11 -176.1(3) C10 C4 C5 C11 1.0(4) N1 C1 C6 C7 -0.2(4) C2 C1 C6 C7 179.6(3) N1 C1 C6 C8 -171.6(3) C2 C1 C6 C8 8.2(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30652202