#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/35/2203526.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_2203526 loop_ _publ_author_name 'Lu, Liping' 'Qin, Shidong' 'Zhu, Miaoli' 'Yang, Pin' _publ_section_title ;4-Dimethylamino-6-(1-methyl-4-nitro-1H-pyrrol-2-yl)-1,3,5-triazine-2-amine dimethylformamide solvate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o583 _journal_page_last o585 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C10 H13 N7 O2 , C3 H7 N O' _chemical_formula_moiety 'C10 H13 N7 O2 , C3 H7 N O' _chemical_formula_sum 'C13 H20 N8 O3' _chemical_formula_weight 336.37 _chemical_name_systematic ; 4-Dimethylamino-6-(1-methyl-4-nitro-1H-pyrrol-2-yl)-1,3,5-triazine-2-amine dimethylformamide solvate ; _space_group_IT_number 60 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_space_group_name_H-M 'P b c n' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 15.810(3) _cell_length_b 7.299(2) _cell_length_c 28.550(6) _cell_measurement_reflns_used 18161 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 24.46 _cell_measurement_theta_min 2.57 _cell_volume 3294.6(13) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1999)' _computing_publication_material SHELXTL/PC _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker SMART 1K CCD area-detector' _diffrn_measurement_method '\f and \w' _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 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 14666 _diffrn_reflns_theta_full 25.01 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 1.43 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_T_max 0.9801 _exptl_absorpt_correction_T_min 0.9703 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2000)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description pillar _exptl_crystal_F_000 1424 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.189 _refine_diff_density_min -0.171 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 222 _refine_ls_number_reflns 2905 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.167 _refine_ls_R_factor_all 0.0975 _refine_ls_R_factor_gt 0.0669 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0562P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1303 _refine_ls_wR_factor_ref 0.1434 _reflns_number_gt 2217 _reflns_number_total 2905 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ww6174.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 'Orthorhombic' changed to 'orthorhombic' 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_cell_volume 3294.6(12) _cod_database_code 2203526 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' 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 C1 0.62007(16) 0.1932(4) 0.31265(11) 0.0381(8) Uani d . 1 C H1A 0.6111 0.1106 0.2861 0.057 Uiso calc R 1 H H1B 0.6149 0.3205 0.3021 0.057 Uiso calc R 1 H H1C 0.5776 0.1686 0.3368 0.057 Uiso calc R 1 H C2 0.78395(15) 0.1916(4) 0.31093(9) 0.0258(6) Uani d . 1 C C3 0.84463(18) 0.1432(4) 0.34253(9) 0.0305(7) Uani d . 1 C H3 0.9041 0.1487 0.3379 0.037 Uiso calc R 1 H C4 0.80301(18) 0.0843(4) 0.38281(9) 0.0318(7) Uani d . 1 C C5 0.71725(18) 0.0978(4) 0.37558(10) 0.0336(7) Uani d . 1 C H5 0.6742 0.0665 0.3974 0.040 Uiso calc R 1 H C6 0.79611(16) 0.2581(3) 0.26292(9) 0.0256(6) Uani d . 1 C C7 0.88620(16) 0.3339(4) 0.20478(9) 0.0276(6) Uani d . 1 C C8 0.74578(16) 0.3543(4) 0.19328(9) 0.0284(6) Uani d . 1 C C9 0.59259(16) 0.3597(4) 0.18197(11) 0.0436(8) Uani d . 1 C H9A 0.5835 0.2270 0.1836 0.065 Uiso calc R 1 H H9B 0.5523 0.4136 0.1598 0.065 Uiso calc R 1 H H9C 0.5841 0.4137 0.2130 0.065 Uiso calc R 1 H C10 0.6897(2) 0.4592(5) 0.11834(10) 0.0476(9) Uani d . 1 C H10A 0.7450 0.5185 0.1151 0.071 Uiso calc R 1 H H10B 0.6450 0.5471 0.1106 0.071 Uiso calc R 1 H H10C 0.6865 0.3544 0.0970 0.071 Uiso calc R 1 H C11 0.97774(19) 0.5928(5) 0.06801(10) 0.0440(8) Uani d . 1 C H11 0.9925 0.7189 0.0674 0.053 Uiso calc R 1 H C12 0.8752(2) 0.6699(6) 0.00862(12) 0.0776(13) Uani d . 1 C H12A 0.8146 0.6719 0.0159 0.116 Uiso calc R 1 H H12B 0.8833 0.6327 -0.0241 0.116 Uiso calc R 1 H H12C 0.8991 0.7924 0.0133 0.116 Uiso calc R 1 H C13 0.8919(2) 0.3509(6) 0.03730(14) 0.0783(13) Uani d . 1 C H13A 0.8897 0.3105 0.0046 0.117 Uiso calc R 1 H H13B 0.8358 0.3376 0.0515 0.117 Uiso calc R 1 H H13C 0.9327 0.2758 0.0546 0.117 Uiso calc R 1 H N1 0.70544(13) 0.1631(3) 0.33216(8) 0.0301(6) Uani d . 1 N N2 0.84171(18) 0.0130(3) 0.42392(9) 0.0439(7) Uani d . 1 N N3 0.87698(13) 0.2760(3) 0.24960(8) 0.0285(6) Uani d . 1 N N4 0.96537(13) 0.3498(3) 0.18872(8) 0.0352(6) Uani d . 1 N H4A 0.9744 0.3868 0.1598 0.042 Uiso calc R 1 H H4B 1.0084 0.3233 0.2071 0.042 Uiso calc R 1 H N5 0.82337(14) 0.3762(3) 0.17528(7) 0.0306(6) Uani d . 1 N N6 0.72847(13) 0.2928(3) 0.23707(8) 0.0291(6) Uani d . 1 N N7 0.67880(14) 0.3964(3) 0.16616(8) 0.0363(6) Uani d . 1 N N8 0.91750(15) 0.5408(4) 0.03915(8) 0.0427(7) Uani d . 1 N O1 0.79633(15) -0.0292(3) 0.45756(8) 0.0619(7) Uani d . 1 O O2 0.91967(15) -0.0028(3) 0.42423(8) 0.0585(7) Uani d . 1 O O3 1.01650(14) 0.4969(3) 0.09527(7) 0.0549(7) Uani d . 1 O 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 C1 0.0240(15) 0.0416(19) 0.0486(19) -0.0024(14) 0.0048(14) -0.0071(16) C2 0.0239(14) 0.0230(15) 0.0306(15) -0.0025(12) 0.0019(12) -0.0042(13) C3 0.0313(16) 0.0280(16) 0.0322(15) -0.0005(13) 0.0041(13) -0.0027(13) C4 0.0390(17) 0.0279(17) 0.0286(16) 0.0000(14) -0.0007(13) -0.0025(13) C5 0.0424(18) 0.0275(17) 0.0309(16) -0.0044(14) 0.0119(14) -0.0010(14) C6 0.0265(15) 0.0177(14) 0.0326(16) -0.0009(12) 0.0019(13) -0.0052(12) C7 0.0280(15) 0.0261(16) 0.0287(15) -0.0028(13) 0.0034(12) -0.0037(13) C8 0.0293(15) 0.0237(15) 0.0321(15) -0.0010(13) -0.0033(13) -0.0035(13) C9 0.0292(16) 0.045(2) 0.057(2) 0.0007(15) -0.0130(15) 0.0009(17) C10 0.049(2) 0.052(2) 0.0428(19) 0.0042(17) -0.0154(15) 0.0020(17) C11 0.0414(19) 0.059(2) 0.0319(17) -0.0093(17) 0.0039(15) -0.0020(17) C12 0.083(3) 0.111(4) 0.040(2) 0.033(3) -0.012(2) -0.006(2) C13 0.076(3) 0.082(3) 0.077(3) -0.037(2) 0.007(2) -0.013(2) N1 0.0308(13) 0.0269(13) 0.0327(14) -0.0029(11) 0.0051(10) -0.0053(11) N2 0.0554(18) 0.0352(16) 0.0410(16) 0.0006(14) -0.0020(14) 0.0023(13) N3 0.0269(13) 0.0308(14) 0.0278(13) -0.0008(11) 0.0021(10) -0.0021(11) N4 0.0292(13) 0.0455(16) 0.0308(13) -0.0003(12) 0.0001(11) 0.0066(12) N5 0.0313(13) 0.0294(14) 0.0310(13) -0.0023(11) -0.0027(11) -0.0003(11) N6 0.0262(12) 0.0275(13) 0.0337(14) -0.0014(10) -0.0006(10) -0.0005(11) N7 0.0315(14) 0.0381(15) 0.0394(15) -0.0023(11) -0.0091(11) 0.0034(12) N8 0.0384(15) 0.061(2) 0.0286(13) -0.0056(14) -0.0064(12) -0.0026(13) O1 0.0750(17) 0.0740(18) 0.0367(13) -0.0099(14) 0.0072(12) 0.0170(13) O2 0.0563(16) 0.0642(17) 0.0549(15) 0.0149(14) -0.0095(12) 0.0121(13) O3 0.0498(14) 0.0819(19) 0.0331(12) -0.0004(13) -0.0078(10) 0.0095(13) 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' O O 0.0106 0.0060 '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 N1 C1 H1A 109.5 ? N1 C1 H1B 109.5 ? H1A C1 H1B 109.5 ? N1 C1 H1C 109.5 ? H1A C1 H1C 109.5 ? H1B C1 H1C 109.5 ? C3 C2 N1 107.4(2) y C3 C2 C6 127.7(2) y N1 C2 C6 124.8(2) y C2 C3 C4 107.1(2) y C2 C3 H3 126.5 ? C4 C3 H3 126.5 ? C5 C4 C3 108.7(2) y C5 C4 N2 125.0(3) y C3 C4 N2 126.2(3) y N1 C5 C4 107.5(2) y N1 C5 H5 126.2 ? C4 C5 H5 126.2 ? N6 C6 N3 126.4(2) y N6 C6 C2 118.6(2) y N3 C6 C2 115.0(2) y N4 C7 N5 117.3(2) y N4 C7 N3 116.8(2) y N5 C7 N3 125.9(2) y N5 C8 N7 118.2(2) y N5 C8 N6 125.3(2) y N7 C8 N6 116.5(2) y N7 C9 H9A 109.5 ? N7 C9 H9B 109.5 ? H9A C9 H9B 109.5 ? N7 C9 H9C 109.5 ? H9A C9 H9C 109.5 ? H9B C9 H9C 109.5 ? N7 C10 H10A 109.5 ? N7 C10 H10B 109.5 ? H10A C10 H10B 109.5 ? N7 C10 H10C 109.5 ? H10A C10 H10C 109.5 ? H10B C10 H10C 109.5 ? O3 C11 N8 127.0(3) ? O3 C11 H11 116.5 ? N8 C11 H11 116.5 ? N8 C12 H12A 109.5 ? N8 C12 H12B 109.5 ? H12A C12 H12B 109.5 ? N8 C12 H12C 109.5 ? H12A C12 H12C 109.5 ? H12B C12 H12C 109.5 ? N8 C13 H13A 109.5 ? N8 C13 H13B 109.5 ? H13A C13 H13B 109.5 ? N8 C13 H13C 109.5 ? H13A C13 H13C 109.5 ? H13B C13 H13C 109.5 ? C5 N1 C2 109.3(2) y C5 N1 C1 121.9(2) y C2 N1 C1 128.8(2) y O1 N2 O2 123.3(3) y O1 N2 C4 118.8(3) y O2 N2 C4 117.9(3) y C6 N3 C7 113.6(2) y C7 N4 H4A 120.0 ? C7 N4 H4B 120.0 ? H4A N4 H4B 120.0 ? C7 N5 C8 114.3(2) y C6 N6 C8 114.5(2) y C8 N7 C10 121.3(2) y C8 N7 C9 120.9(2) y C10 N7 C9 117.4(2) y C11 N8 C13 120.2(3) ? C11 N8 C12 121.6(3) ? C13 N8 C12 118.2(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 N1 1.476(3) y C1 H1A 0.9800 ? C1 H1B 0.9800 ? C1 H1C 0.9800 ? C2 C3 1.364(4) y C2 N1 1.397(3) y C2 C6 1.467(4) y C3 C4 1.393(4) y C3 H3 0.9500 ? C4 C5 1.375(4) y C4 N2 1.422(4) y C5 N1 1.341(3) y C5 H5 0.9500 ? C6 N6 1.324(3) y C6 N3 1.340(3) y C7 N4 1.338(3) y C7 N5 1.338(3) y C7 N3 1.355(3) y C8 N5 1.340(3) y C8 N7 1.347(3) y C8 N6 1.356(3) y C9 N7 1.461(3) y C9 H9A 0.9800 ? C9 H9B 0.9800 ? C9 H9C 0.9800 ? C10 N7 1.451(4) y C10 H10A 0.9800 ? C10 H10B 0.9800 ? C10 H10C 0.9800 ? C11 O3 1.213(3) ? C11 N8 1.315(4) ? C11 H11 0.9500 ? C12 N8 1.447(4) ? C12 H12A 0.9800 ? C12 H12B 0.9800 ? C12 H12C 0.9800 ? C13 N8 1.445(4) ? C13 H13A 0.9800 ? C13 H13B 0.9800 ? C13 H13C 0.9800 ? N2 O1 1.238(3) ? N2 O2 1.238(3) ? N4 H4A 0.8800 ? N4 H4B 0.8800 ? 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 N4 H4A O3 . 0.88 2.12 2.987(3) 170 y N4 H4B N3 3_755 0.88 2.22 3.099(3) 175 y 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 N1 C2 C3 C4 0.4(3) C6 C2 C3 C4 -178.4(3) C2 C3 C4 C5 -0.2(3) C2 C3 C4 N2 176.8(3) C3 C4 C5 N1 0.0(3) N2 C4 C5 N1 -177.1(3) C3 C2 C6 N6 177.9(3) N1 C2 C6 N6 -0.7(4) C3 C2 C6 N3 -1.6(4) N1 C2 C6 N3 179.9(2) C4 C5 N1 C2 0.2(3) C4 C5 N1 C1 179.5(2) C3 C2 N1 C5 -0.4(3) C6 C2 N1 C5 178.4(2) C3 C2 N1 C1 -179.5(2) C6 C2 N1 C1 -0.7(4) C5 C4 N2 O1 -5.4(4) C3 C4 N2 O1 178.0(3) C5 C4 N2 O2 175.0(3) C3 C4 N2 O2 -1.6(4) N6 C6 N3 C7 -0.8(4) C2 C6 N3 C7 178.7(2) N4 C7 N3 C6 -178.2(2) N5 C7 N3 C6 1.8(4) N4 C7 N5 C8 178.9(2) N3 C7 N5 C8 -1.0(4) N7 C8 N5 C7 179.0(2) N6 C8 N5 C7 -0.9(4) N3 C6 N6 C8 -0.8(4) C2 C6 N6 C8 179.7(2) N5 C8 N6 C6 1.8(4) N7 C8 N6 C6 -178.2(2) N5 C8 N7 C10 1.6(4) N6 C8 N7 C10 -178.5(3) N5 C8 N7 C9 174.2(2) N6 C8 N7 C9 -5.8(4) O3 C11 N8 C13 -0.8(5) O3 C11 N8 C12 179.2(3) _cod_database_fobs_code 2203526