#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011341.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_2011341 loop_ _publ_author_name 'Ko\a:1',2'-d]pyrazinediylium dichloride dihydrate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1144 _journal_page_last 1145 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C16 H20 N2 O2 2+ , 2Cl - , 2H2 O' _chemical_formula_sum 'C16 H24 Cl2 N2 O4' _chemical_formula_weight 379.28 _chemical_name_systematic ; 6,12-Dihydro-2,8-dihydroxy-1,3,7,9-tetramethyl-dipyrido[1,2-a:1',2'-d] pyrazinediylium dichloride dihydrate ; _space_group_IT_number 12 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-I 2y' _symmetry_space_group_name_H-M 'I 1 2/m 1' _cell_angle_alpha 90.00 _cell_angle_beta 104.15(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 11.255(15) _cell_length_b 6.8650(13) _cell_length_c 11.9530(12) _cell_measurement_reflns_used 10 _cell_measurement_temperature 293 _cell_measurement_theta_max 14.25 _cell_measurement_theta_min 6.38 _cell_volume 895.5(12) _computing_cell_refinement STADI4 _computing_data_collection 'STADI4 (Stoe & Cie, 1996a)' _computing_data_reduction 'XRED (Stoe & Cie, 1996b)' _computing_molecular_graphics 'PLATON2000 (Spek, 2000)' _computing_publication_material 'SHELXL97 and PARST96 (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Philips PW1100 upgraded by Stoe & Cie' _diffrn_measurement_method \w-scan _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Molybdenum K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0206 _diffrn_reflns_av_sigmaI/netI .0103 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2776 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 3.00 _diffrn_standards_decay_% 1.0 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .385 _exptl_absorpt_correction_T_max .888 _exptl_absorpt_correction_T_min .801 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 1996b)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 400 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .45 _exptl_crystal_size_min .40 _refine_diff_density_max .357 _refine_diff_density_min -.326 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 78 _refine_ls_number_reflns 1388 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.113 _refine_ls_R_factor_all .0594 _refine_ls_R_factor_gt .0477 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0895P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1685 _reflns_number_gt 1146 _reflns_number_total 1388 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na1479.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'I 2/m' _cod_database_code 2011341 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y,-z x+1/2,y+1/2,z+1/2 -x+1/2,y+1/2,-z+1/2 -x,-y,-z x,-y,z -x+1/2,-y+1/2,-z+1/2 x+1/2,-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_type_symbol Cl1 .70308(5) .0000 .11959(5) .0599(3) Uani d S 1 Cl O1W .43032(18) .0000 .13863(17) .0822(9) Uani d S 1 O H1W .4015(12) .0000 .070(3) .090(14) Uiso d SR 1 H H2W .495(3) .0000 .1464(3) .086(13) Uiso d SR 1 H N5 .01901(14) .0000 .38809(14) .0343(4) Uani d S 1 N O2' .35773(15) .0000 .32597(15) .0652(6) Uani d S 1 O H2' .3673(5) .0000 .262(3) .060(9) Uiso d SR 1 H C13 .11818(16) .0000 .47604(16) .0344(4) Uani d S 1 C C6 -.10741(17) .0000 .40238(17) .0424(5) Uani d S 1 C H6A -.1494 -.1140 .3639 .051 Uiso calc PR .50 H C1 .23454(18) .0000 .45637(18) .0429(5) Uani d S 1 C C1' .34721(19) .0000 .5551(2) .0578(7) Uani d S 1 C H1'1 .4191 .0000 .5253 .087 Uiso calc SR 1 H H1'2 .3472 -.1142 .6015 .087 Uiso calc PR .50 H C2 .24504(19) .0000 .34112(19) .0488(6) Uani d S 1 C C4 .02755(19) .0000 .27661(18) .0426(5) Uani d S 1 C H4 -.0436 .0000 .2174 .051 Uiso calc SR 1 H C3' .1451(2) .0000 .1251(2) .0682(9) Uani d S 1 C H3'1 .2292 .0000 .1209 .102 Uiso calc SR 1 H H3'2 .1049 .1142 .0875 .102 Uiso calc PR .50 H C3 .1392(2) .0000 .25002(18) .0481(6) Uani d S 1 C 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 Cl1 .0415(4) .0965(6) .0401(4) .000 .0067(2) .000 O1W .0398(9) .174(3) .0367(9) .000 .0161(7) .000 N5 .0242(7) .0509(9) .0276(7) .000 .0062(5) .000 O2' .0291(7) .1341(18) .0354(9) .000 .0134(6) .000 C13 .0255(8) .0505(10) .0277(8) .000 .0072(6) .000 C6 .0230(8) .0761(14) .0277(9) .000 .0055(7) .000 C1 .0246(8) .0752(14) .0284(9) .000 .0052(7) .000 C1' .0238(8) .115(2) .0329(10) .000 .0043(7) .000 C2 .0270(9) .0885(17) .0318(10) .000 .0091(7) .000 C4 .0299(8) .0692(14) .0279(8) .000 .0058(7) .000 C3' .0393(11) .136(3) .0297(10) .000 .0099(9) .000 C3 .0314(9) .0851(16) .0280(9) .000 .0074(7) .000 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .0033 .0016 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H .0000 .0000 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl .1484 .1585 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N .0061 .0033 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O .0106 .0060 ' 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 0 -1 -5 0 -4 0 -4 -1 -1 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 H1W O1W H2W . . 106.3 ? C13 N5 C4 . . 121.8(2) ? C13 N5 C6 . . 123.7(2) yes C4 N5 C6 . . 114.5(2) yes C2 O2' H2' . . 119.3 ? N5 C13 C1 . . 120.7(2) ? N5 C13 C6 . 5_556 121.2(2) ? C1 C13 C6 . 5_556 118.2(2) ? N5 C6 C13 . 5_556 115.1(2) ? N5 C6 H6A . . 108.5 ? C13 C6 H6A 5_556 . 108.5 ? N5 C6 H6B . . 108.5 ? C13 C6 H6B 5_556 . 108.5 ? H6A C6 H6B . . 107.5 ? C13 C1 C2 . . 118.3(2) ? C13 C1 C1' . . 121.1(2) ? C2 C1 C1' . . 120.6(2) ? C1 C1' H1'1 . . 109.5 ? C1 C1' H1'2 . . 109.5 ? H1'1 C1' H1'2 . . 109.5 ? C1 C1' H1'3 . . 109.5 ? H1'1 C1' H1'3 . . 109.5 ? H1'2 C1' H1'3 . . 109.5 ? O2' C2 C3 . . 123.6(2) ? O2' C2 C1 . . 116.4(2) ? C3 C2 C1 . . 120.0(2) ? N5 C4 C3 . . 121.1(2) ? N5 C4 H4 . . 119.5 ? C3 C4 H4 . . 119.5 ? C3 C3' H3'1 . . 109.5 ? C3 C3' H3'2 . . 109.5 ? H3'1 C3' H3'2 . . 109.5 ? C3 C3' H3'3 . . 109.5 ? H3'1 C3' H3'3 . . 109.5 ? H3'2 C3' H3'3 . . 109.5 ? C4 C3 C2 . . 118.2(2) ? C4 C3 C3' . . 119.6(2) ? C2 C3 C3' . . 122.2(2) ? 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 O1W H1W . .81(3) ? O1W H2W . .71(3) ? N5 C13 . 1.333(3) yes N5 C4 . 1.359(3) yes N5 C6 . 1.474(3) yes O2' C2 . 1.324(3) yes O2' H2' . .80(3) ? C13 C1 . 1.386(3) yes C13 C6 5_556 1.488(3) ? C6 C13 5_556 1.488(3) ? C6 H6A . .97 ? C6 H6B . .97 ? C1 C2 . 1.411(3) yes C1 C1' . 1.506(3) yes C1' H1'1 . .96 ? C1' H1'2 . .96 ? C1' H1'3 . .96 ? C2 C3 . 1.403(3) yes C4 C3 . 1.370(3) yes C4 H4 . .93 ? C3' C3 . 1.510(3) yes C3' H3'1 . .96 ? C3' H3'2 . .96 ? C3' H3'3 . .96 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _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 O2' H2' O1W 1 1 .80(3) 1.79(3) 2.564(4) 165(2) yes O1W H2W Cl1 1 1 .71(3) 2.44(3) 3.133(5) 165(4) yes O1W H1W Cl1 1 2_655 .81(3) 2.28(3) 3.085(5) 173(2) yes C4 H4 Cl1 1 1_455 .93 2.81 3.675(5) 156 yes C6 H6A Cl1 1 4_545 .97 2.74 3.588(5) 147 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion C4 N5 C13 C1 . . .0 C6 N5 C13 C1 . . 180.0 C4 N5 C13 C6 . 5_556 180.0 C6 N5 C13 C6 . 5_556 .0 C13 N5 C6 C13 . 5_556 .0 C4 N5 C6 C13 . 5_556 180.0 N5 C13 C1 C2 . . .0 C6 C13 C1 C2 5_556 . 180.0 N5 C13 C1 C1' . . 180.0 C6 C13 C1 C1' 5_556 . .0 C13 C1 C2 O2' . . 180.0 C1' C1 C2 O2' . . .0 C13 C1 C2 C3 . . .0 C1' C1 C2 C3 . . 180.0 C13 N5 C4 C3 . . .0 C6 N5 C4 C3 . . 180.0 N5 C4 C3 C2 . . .0 N5 C4 C3 C3' . . 180.0 O2' C2 C3 C4 . . 180.0 C1 C2 C3 C4 . . .0 O2' C2 C3 C3' . . .0 C1 C2 C3 C3' . . 180.0