#------------------------------------------------------------------------------ #$Date: 2015-01-23 12:30:19 +0000 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/85/2008582.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_2008582 loop_ _publ_author_name 'Bartnik, Romuald' 'Faure, Ren\'e' 'Gebicki, Krzysztof' _publ_section_title ; Dimorphism of 2,3,5,6-tetraphenylpyrazine ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1034 _journal_page_last 1037 _journal_paper_doi 10.1107/S0108270199002450 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C28 H20 N2' _chemical_formula_structural 'C28 H20 N2' _chemical_formula_sum 'C28 H20 N2' _chemical_formula_weight 384.48 _chemical_name_systematic ; 2,3,5,6-tetraphenylpyrazine (\b form) ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _cell_angle_alpha 90 _cell_angle_beta 92.180(10) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 18.654(3) _cell_length_b 23.509(2) _cell_length_c 9.5760(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 291 _cell_measurement_theta_max 50.10 _cell_measurement_theta_min 8.55 _cell_volume 4196.4(9) _computing_cell_refinement 'CAD4 Software' _computing_data_collection 'CAD4 Software (Enraf Nonius, 1985)' _computing_data_reduction 'SDP (Frenz, 1982)' _computing_molecular_graphics 'ORTEP (Johnson, 1965) ' _computing_publication_material 'PLATON (Spek, 1990)' _computing_structure_refinement SDP _computing_structure_solution SDP _diffrn_ambient_temperature 291 _diffrn_measurement_device 'Enraf-Nonius CAD4 ' _diffrn_measurement_method '\w--4/3\q scans ' _diffrn_radiation_monochromator ' graphite ' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54056 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 4043 _diffrn_reflns_reduction_process ; ? ; _diffrn_reflns_theta_max 73 _diffrn_reflns_theta_min 1 _diffrn_standards_decay_% 0.2 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.55 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details ' (North et al., 1968) ' _exptl_crystal_colour ' colourless ' _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_meas ? _exptl_crystal_description ' needle ' _exptl_crystal_F_000 1616 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.206 _refine_diff_density_min -0.197 _refine_ls_abs_structure_details ; ? ; _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.24 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 272 _refine_ls_number_reflns 3583 _refine_ls_R_factor_obs .057 _refine_ls_shift/su_max 0.00 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme ' w = 4F~O~^2^[\s^2^(I) + (0.04F~O~^2^)^2^]^-1^ ' _refine_ls_wR_factor_obs .077 _reflns_number_observed 3583 _reflns_number_total 4043 _reflns_observed_criterion ' I~net~> 0 ' _[local]_cod_data_source_file ln1076.cif _[local]_cod_data_source_block beta _[local]_cod_cif_authors_sg_H-M 'C 2/c' _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. '_refine_ls_hydrogen_treatment' value ' noref ' changed to 'noref' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_refine_ls_matrix_type' value ' full ' changed to 'full' 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 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_cell_volume 4196.6(8) _cod_database_code 2008582 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y,1/2-z -x,-y,-z x,-y,1/2+z 1/2+x,1/2+y,z 1/2-x,1/2+y,1/2-z 1/2-x,1/2-y,-z 1/2+x,1/2-y,1/2+z 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 N110 .0378(7) .0375(7) .0484(9) .0000 .0009(7) .0000 N140 .0425(8) .0392(7) .0413(9) .0000 .0000(7) .0000 C120 .0377(6) .0377(6) .0434(7) .0029(5) .0021(5) -.0029(5) C121 .0436(6) .0382(6) .0460(8) -.0021(6) -.0020(6) .0019(6) C122 .0635(9) .0409(7) .0532(9) -.0081(6) .0126(7) -.0019(6) C123 .0940(10) .0498(7) .0530(10) -.0251(8) .0048(9) -.0050(7) C124 .0780(10) .0610(9) .0720(10) -.0272(8) -.0252(8) .0095(8) C125 .0445(8) .0650(10) .122(2) -.0036(8) -.0197(9) .0110(10) C126 .0416(7) .0476(8) .0930(10) .0036(6) -.0046(8) -.0067(8) C130 .0389(6) .0391(6) .0418(7) .0003(5) .0026(5) -.0027(5) C131 .0400(6) .0391(6) .0438(7) .0007(5) .0010(5) -.0002(6) C132 .0633(9) .0490(7) .0484(9) .0102(7) -.0062(7) -.0059(7) C133 .0780(10) .0651(9) .0481(9) .0116(9) -.0142(8) -.0020(8) C134 .0643(9) .0573(8) .0620(10) .0130(8) -.0092(8) .0100(8) C135 .0629(9) .0436(7) .0640(10) .0106(7) -.0025(8) .0000(7) C136 .0523(7) .0415(7) .0505(8) .0037(6) -.0018(6) -.0031(6) N210 .0428(5) .0410(5) .0476(6) -.0013(5) .0052(5) -.0012(5) C220 .0414(6) .0400(6) .0423(7) -.0007(5) .0018(6) .0003(5) C221 .0419(6) .0391(6) .0478(8) -.0015(5) .0005(6) .0031(6) C222 .0634(9) .0465(7) .0560(10) -.0063(7) .0026(8) -.0040(7) C223 .0740(10) .0458(8) .0800(10) -.0114(8) -.0084(9) -.0040(8) C224 .0615(9) .0507(8) .0920(10) -.0136(7) -.0015(9) .0187(8) C225 .0605(9) .0623(9) .0670(10) -.0068(8) .0095(8) .0192(8) C226 .0503(8) .0535(8) .0501(9) -.0023(7) .0037(7) .0041(7) C260 .0423(6) .0409(6) .0483(8) -.0009(6) .0046(6) -.0011(6) C261 .0503(7) .0404(6) .0513(8) .0024(6) .0121(6) .0034(6) C262 .0700(10) .0494(8) .0820(10) -.0084(8) .0177(9) -.0134(8) C263 .1050(10) .0486(8) .0900(10) -.0138(9) .0330(10) -.0174(8) C264 .1070(10) .0436(8) .0810(10) .0151(9) .0423(9) .0043(8) C265 .0770(10) .0700(10) .0720(10) .0253(8) .0247(8) .0063(9) C266 .0549(8) .0621(9) .0600(10) .0106(7) .0123(7) .0002(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_occupancy N110 .0 -.00293(7) .250 .0413(7) Uani 1.000 N140 .0 .11376(7) .250 .0410(8) Uani 1.000 C120 .05322(7) .02554(6) .3171(2) .0396(6) Uani 1.000 C121 .11183(7) -.01022(6) .3789(2) .0427(6) Uani 1.000 C122 .09490(9) -.05742(6) .4572(2) .0523(9) Uani 1.000 C123 .14840(10) -.09072(7) .5192(2) .0660(10) Uani 1.000 C124 .21930(10) -.07865(8) .4986(2) .0710(10) Uani 1.000 C125 .23678(9) -.03317(8) .4156(3) .0777(8) Uani 1.000 C126 .18334(8) .00157(7) .3578(2) .0608(7) Uani 1.000 C130 .04971(7) .08534(6) .32690(10) .0399(6) Uani 1.000 C131 .09644(7) .12136(6) .41970(10) .0410(6) Uani 1.000 C132 .11833(9) .10426(7) .5533(2) .0538(9) Uani 1.000 C133 .15790(10) .14048(8) .6400(2) .0640(10) Uani 1.000 C134 .17590(10) .19414(7) .5958(2) .0614(9) Uani 1.000 C135 .15461(9) .21157(6) .4631(2) .0570(10) Uani 1.000 C136 .11481(8) .17584(6) .3760(2) .0482(7) Uani 1.000 N210 .06030(6) .44339(5) .17140(10) .0437(5) Uani 1.000 C220 .03222(7) .49267(5) .21410(10) .0412(6) Uani 1.000 C221 .07453(7) .54435(6) .1813(2) .0430(6) Uani 1.000 C222 .08605(9) .58767(7) .2780(2) .0554(9) Uani 1.000 C223 .12990(10) .63325(7) .2475(2) .0670(10) Uani 1.000 C224 .16330(10) .63557(7) .1208(2) .0681(9) Uani 1.000 C225 .15210(10) .59289(8) .0245(2) .0632(9) Uani 1.000 C226 .10771(9) .54731(6) .0538(2) .0513(8) Uani 1.000 C260 .02930(7) .39430(6) .2055(2) .0438(6) Uani 1.000 C261 .06021(8) .34212(6) .1438(2) .0471(7) Uani 1.000 C262 .01670(10) .30229(7) .0759(2) .0670(10) Uani 1.000 C263 .04710(10) .25572(8) .0116(2) .0800(10) Uani 1.000 C264 .12030(10) .24825(7) .0171(2) .0760(10) Uani 1.000 C265 .16330(10) .28687(8) .0858(2) .0720(10) Uani 1.000 C266 .13415(9) .33436(7) .1483(2) .0589(8) Uani 1.000 H122 .046 -.067 .468 .0500 Uiso 1.000 H123 .136 -.122 .576 .0500 Uiso 1.000 H124 .256 -.101 .541 .0500 Uiso 1.000 H125 .286 -.026 .398 .0500 Uiso 1.000 H126 .196 .034 .303 .0500 Uiso 1.000 H132 .106 .067 .585 .0500 Uiso 1.000 H133 .173 .128 .731 .0500 Uiso 1.000 H134 .203 .219 .656 .0500 Uiso 1.000 H135 .167 .248 .431 .0500 Uiso 1.000 H136 .100 .188 .285 .0500 Uiso 1.000 H222 .064 .586 .366 .0500 Uiso 1.000 H223 .137 .663 .314 .0500 Uiso 1.000 H224 .194 .667 .101 .0500 Uiso 1.000 H225 .175 .595 -.062 .0500 Uiso 1.000 H226 .100 .518 -.014 .0500 Uiso 1.000 H262 -.034 .307 .074 .0500 Uiso 1.000 H263 .017 .229 -.037 .0500 Uiso 1.000 H264 .141 .216 -.026 .0500 Uiso 1.000 H265 .214 .281 .090 .0500 Uiso 1.000 H266 .165 .361 .195 .0500 Uiso 1.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0311 0.0180 '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' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -9 -9 4 3 -1 -1 8 8 4 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C120 N110 C120 . 2_555 120.10(10) no C130 N140 C130 . 2_555 120.20(10) no N110 C120 C121 . . 115.40(10) no N110 C120 C130 . . 119.60(10) no C121 C120 C130 . . 125.00(10) no C120 C121 C122 . . 119.40(10) no C120 C121 C126 . . 121.80(10) no C122 C121 C126 . . 118.80(10) no C121 C122 C123 . . 120.7(2) no C122 C123 C124 . . 120.2(2) no C123 C124 C125 . . 119.6(2) no C124 C125 C126 . . 120.3(2) no C121 C126 C125 . . 120.4(2) no N140 C130 C120 . . 119.50(10) no N140 C130 C131 . . 115.00(10) no C120 C130 C131 . . 125.50(10) no C130 C131 C132 . . 122.10(10) no C130 C131 C136 . . 119.30(10) no C132 C131 C136 . . 118.40(10) no C131 C132 C133 . . 120.4(2) no C132 C133 C134 . . 120.7(2) no C133 C134 C135 . . 119.4(2) no C134 C135 C136 . . 120.3(2) no C131 C136 C135 . . 120.7(2) no C121 C122 H122 . . 120 no C123 C122 H122 . . 120 no C122 C123 H123 . . 120 no C124 C123 H123 . . 120 no C123 C124 H124 . . 120 no C125 C124 H124 . . 120 no C124 C125 H125 . . 120 no C126 C125 H125 . . 120 no C121 C126 H126 . . 120 no C125 C126 H126 . . 120 no C131 C132 H132 . . 120 no C133 C132 H132 . . 120 no C132 C133 H133 . . 120 no C134 C133 H133 . . 120 no C133 C134 H134 . . 120 no C135 C134 H134 . . 120 no C134 C135 H135 . . 120 no C136 C135 H135 . . 120 no C131 C136 H136 . . 120 no C135 C136 H136 . . 120 no C220 N210 C260 . . 119.60(10) no N210 C220 C221 . . 115.10(10) no N210 C220 C220 . 2_555 120.00(10) no C220 C220 C221 2_555 . 124.90(10) no C220 C221 C222 . . 121.90(10) no C220 C221 C226 . . 118.90(10) no C222 C221 C226 . . 119.00(10) no C221 C222 C223 . . 120.3(2) no C222 C223 C224 . . 120.2(2) no C223 C224 C225 . . 119.8(2) no C224 C225 C226 . . 120.3(2) no C221 C226 C225 . . 120.3(2) no N210 C260 C261 . . 115.90(10) no N210 C260 C260 . 2_555 120.00(10) no C260 C260 C261 2_555 . 124.10(10) no C260 C261 C262 . . 121.00(10) no C260 C261 C266 . . 119.70(10) no C262 C261 C266 . . 119.20(10) no C261 C262 C263 . . 120.0(2) no C262 C263 C264 . . 120.3(2) no C263 C264 C265 . . 119.9(2) no C264 C265 C266 . . 120.6(2) no C261 C266 C265 . . 119.8(2) no C221 C222 H222 . . 120 no C223 C222 H222 . . 120 no C222 C223 H223 . . 120 no C224 C223 H223 . . 120 no C223 C224 H224 . . 120 no C225 C224 H224 . . 120 no C224 C225 H225 . . 120 no C226 C225 H225 . . 120 no C221 C226 H226 . . 120 no C225 C226 H226 . . 120 no C261 C262 H262 . . 120 no C263 C262 H262 . . 120 no C262 C263 H263 . . 120 no C264 C263 H263 . . 120 no C263 C264 H264 . . 120 no C265 C264 H264 . . 120 no C264 C265 H265 . . 120 no C266 C265 H265 . . 120 no C261 C266 H266 . . 120 no C265 C266 H266 . . 120 no 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 N110 C120 . . 1.341(2) no N140 C130 . . 1.340(2) no C120 C121 . . 1.484(2) no C120 C130 . . 1.411(2) no C121 C122 . . 1.383(2) no C121 C126 . . 1.385(2) no C122 C123 . . 1.384(3) no C123 C124 . . 1.374(3) no C124 C125 . . 1.379(3) no C125 C126 . . 1.387(3) no C130 C131 . . 1.486(2) no C131 C132 . . 1.388(2) no C131 C136 . . 1.394(2) no C132 C133 . . 1.383(2) no C133 C134 . . 1.376(3) no C134 C135 . . 1.378(3) no C135 C136 . . 1.381(2) no C122 H122 . . .95 no C123 H123 . . .95 no C124 H124 . . .95 no C125 H125 . . .95 no C126 H126 . . .95 no C132 H132 . . .95 no C133 H133 . . .95 no C134 H134 . . .95 no C135 H135 . . .95 no C136 H136 . . .95 no N210 C220 . . 1.342(2) no N210 C260 . . 1.337(2) no C220 C221 . . 1.489(2) no C220 C220 . 2_555 1.408(2) no C221 C222 . . 1.387(2) no C221 C226 . . 1.392(2) no C222 C223 . . 1.386(2) no C223 C224 . . 1.386(3) no C224 C225 . . 1.373(3) no C225 C226 . . 1.389(2) no C260 C261 . . 1.488(2) no C260 C260 . 2_555 1.412(2) no C261 C262 . . 1.385(2) no C261 C266 . . 1.390(2) no C262 C263 . . 1.388(3) no C263 C264 . . 1.375(3) no C264 C265 . . 1.365(3) no C265 C266 . . 1.387(3) no C222 H222 . . .95 no C223 H223 . . .95 no C224 H224 . . .95 no C225 H225 . . .95 no C226 H226 . . .95 no C262 H262 . . .95 no C263 H263 . . .95 no C264 H264 . . .95 no C265 H265 . . .95 no C266 H266 . . .95 no 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C120 N110 C120 C121 2_555 . -175.75(12) no C120 N110 C120 C130 2_555 . 5.43(19) no C130 N140 C130 C120 2_555 . 5.43(19) no C130 N140 C130 C131 2_555 . -173.33(12) no N110 C120 C121 C122 . . -47.56(19) no N110 C120 C121 C126 . . 131.01(15) no C130 C120 C121 C122 . . 131.19(16) no C130 C120 C121 C126 . . -50.2(2) no N110 C120 C130 N140 . . -11.1(2) no N110 C120 C130 C131 . . 167.50(13) no C121 C120 C130 N140 . . 170.15(13) no C121 C120 C130 C131 . . -11.2(2) no C120 C121 C122 C123 . . -178.27(15) no C126 C121 C122 C123 . . 3.1(2) no C120 C121 C126 C125 . . -179.17(16) no C122 C121 C126 C125 . . -0.6(3) no C121 C122 C123 C124 . . -2.8(3) no C122 C123 C124 C125 . . -0.1(3) no C123 C124 C125 C126 . . 2.6(3) no C124 C125 C126 C121 . . -2.3(3) no N140 C130 C131 C132 . . 141.36(14) no N140 C130 C131 C136 . . -33.80(19) no C120 C130 C131 C132 . . -37.3(2) no C120 C130 C131 C136 . . 147.50(15) no C130 C131 C132 C133 . . -175.72(15) no C136 C131 C132 C133 . . -0.5(2) no C130 C131 C136 C135 . . 176.16(14) no C132 C131 C136 C135 . . 0.8(2) no C131 C132 C133 C134 . . 0.4(3) no C132 C133 C134 C135 . . -0.6(3) no C133 C134 C135 C136 . . 0.9(3) no C134 C135 C136 C131 . . -1.0(3) no C260 N210 C220 C221 . . 174.76(13) no C260 N210 C220 C220 . 2_555 -4.4(2) no C220 N210 C260 C261 . . 174.99(13) no C220 N210 C260 C260 . 2_555 -4.7(2) no N210 C220 C221 C222 . . -136.84(15) no N210 C220 C221 C226 . . 38.5(2) no C220 C220 C221 C222 2_555 . 42.3(2) no C220 C220 C221 C226 2_555 . -142.43(16) no C220 C221 C222 C223 . . 175.41(16) no C226 C221 C222 C223 . . 0.1(3) no C220 C221 C226 C225 . . -175.03(15) no C222 C221 C226 C225 . . 0.4(3) no C221 C222 C223 C224 . . -0.8(3) no C222 C223 C224 C225 . . 0.9(3) no C223 C224 C225 C226 . . -0.4(3) no C224 C225 C226 C221 . . -0.3(3) no N210 C260 C261 C262 . . -129.95(16) no N210 C260 C261 C266 . . 47.0(2) no C260 C260 C261 C262 2_555 . 49.7(2) no C260 C260 C261 C266 2_555 . -133.35(17) no C260 C261 C262 C263 . . 176.00(17) no C266 C261 C262 C263 . . -0.9(3) no C260 C261 C266 C265 . . -177.41(16) no C262 C261 C266 C265 . . -0.4(3) no C261 C262 C263 C264 . . 1.3(3) no C262 C263 C264 C265 . . -0.2(3) no C263 C264 C265 C266 . . -1.2(3) no C264 C265 C266 C261 . . 1.5(3) no