# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address _publ_author_footnote 'C. Wilson' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Martin S. Adam' ; ? # Address 2 ; ; ? # Footnote 2 ; 'Andrew Parkin' '' '' 'Lynne H. Thomas' '' '' _publ_contact_author_name 'C. Wilson' _publ_contact_author_email CHICK@CHEM.GLA.AC.UK _publ_section_title ; Bifurcated hydrogen bonded supramolecular units in molecular complexes of picolines with chloranilic acid ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Nowhere, Nowhere, NO1 4T, UK. ; _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_phone '+44 1865 000000' # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures have been sent by mail. ; _publ_requested_category CO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment '4pic_1_1_100.cif' data_4pic_1_1_100 _database_code_depnum_ccdc_archive 'CCDC 737688' _chemical_name_systematic '4-picoline chloranilate' _chemical_melting_point ? _cell_length_a 15.617(7) _cell_length_b 4.819(2) _cell_length_c 16.300(7) _cell_angle_alpha 90 _cell_angle_beta 90.270(17) _cell_angle_gamma 90 _cell_volume 1226.7(9) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall ? 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_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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C12 H12 Cl2 N2 O4 # Dc = 1.73 Fooo = 616.00 Mu = 5.45 M = 319.14 # Found Formula = C12 H9 Cl2 N1 O4 # Dc = 1.64 FOOO = 616.00 Mu = 5.38 M = 302.11 _chemical_formula_sum 'C12 H9 Cl2 N1 O4' _chemical_formula_moiety '(C6 Cl2 O4 H), (C6 N1 H8)' _chemical_compound_source ? _chemical_formula_weight 302.11 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 100 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.15 _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.538 # Sheldrick geometric approximatio 0.95 0.92 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9225 _exptl_absorpt_correction_T_max 0.9476 _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 14085 _reflns_number_total 2811 _diffrn_reflns_av_R_equivalents 0.1359 # Number of reflections with Friedels Law is 2812 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2813 _diffrn_reflns_theta_min 3.605 _diffrn_reflns_theta_max 27.481 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.481 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -20 _reflns_limit_h_max 20 _reflns_limit_k_min 0 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.58 _refine_diff_density_max 0.55 _refine_ls_number_reflns 2811 _refine_ls_number_restraints 0 _refine_ls_number_parameters 197 #_refine_ls_R_factor_ref 0.0927 _refine_ls_wR_factor_ref 0.1139 _refine_ls_goodness_of_fit_ref 0.895 #_reflns_number_all 2812 _refine_ls_R_factor_all 0.0874 _refine_ls_wR_factor_all 0.1139 _reflns_threshold_expression >2\s(I) _reflns_number_gt 1811 _refine_ls_R_factor_gt 0.0548 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0757P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.71769(18) 0.5679(7) 0.90010(17) 0.0152(6) Uani d . 1 . . C C2 0.64040(19) 0.6044(7) 0.94358(18) 0.0178(7) Uani d . 1 . . C C3 0.63872(18) 0.8223(7) 1.01043(18) 0.0184(7) Uani d . 1 . . C C4 0.70667(19) 0.9841(7) 1.02823(17) 0.0175(7) Uani d . 1 . . C C5 0.78654(19) 0.9483(7) 0.98389(18) 0.0181(7) Uani d . 1 . . C C6 0.79002(19) 0.7322(7) 0.91493(18) 0.0185(7) Uani d . 1 . . C O7 0.85922(13) 0.7171(5) 0.87612(13) 0.0204(5) Uani d . 1 . . O O8 0.85123(13) 1.0832(5) 0.99916(13) 0.0226(5) Uani d . 1 . . O Cl9 0.70180(5) 1.22948(18) 1.10531(5) 0.0221(2) Uani d . 1 . . Cl O10 0.56581(13) 0.8459(5) 1.05082(13) 0.0218(5) Uani d . 1 . . O O11 0.57296(13) 0.4707(5) 0.93238(13) 0.0224(5) Uani d . 1 . . O Cl12 0.72125(5) 0.31625(17) 0.82409(4) 0.0193(2) Uani d . 1 . . Cl C13 1.0589(2) 1.5795(8) 0.78390(19) 0.0220(7) Uani d . 1 . . C C14 1.0668(2) 1.4901(8) 0.8653(2) 0.0239(8) Uani d . 1 . . C C15 1.0140(2) 1.2847(8) 0.8947(2) 0.0227(8) Uani d . 1 . . C N16 0.95525(16) 1.1677(6) 0.84601(17) 0.0217(6) Uani d . 1 . . N C17 0.9449(2) 1.2480(8) 0.7677(2) 0.0255(8) Uani d . 1 . . C C18 0.9961(2) 1.4535(8) 0.7357(2) 0.0254(8) Uani d . 1 . . C C19 1.1175(2) 1.7967(8) 0.7498(2) 0.0260(8) Uani d . 1 . . C H191 1.169 1.7104 0.7304 0.039 Uiso calc R 1 . . H H192 1.1315 1.9283 0.792 0.039 Uiso calc R 1 . . H H193 1.0896 1.8904 0.7051 0.039 Uiso calc R 1 . . H H141 1.105(2) 1.575(8) 0.902(2) 0.025(9) Uiso d . 1 . . H H181 0.988(2) 1.516(9) 0.679(2) 0.035(10) Uiso d . 1 . . H H9 0.528(3) 0.691(11) 1.031(3) 0.073(17) Uiso d . 1 . . H H10 0.915(3) 1.016(10) 0.870(3) 0.056(13) Uiso d . 1 . . H H151 1.014(2) 1.225(7) 0.946(2) 0.008(8) Uiso d . 1 . . H H171 0.901(2) 1.158(8) 0.7351(19) 0.018(9) Uiso d . 1 . . H 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 0.0161(14) 0.0138(17) 0.0157(15) -0.0002(13) 0.0014(11) -0.0031(12) C2 0.0161(15) 0.0219(19) 0.0153(15) -0.0011(14) -0.0020(11) 0.0023(12) C3 0.0155(15) 0.024(2) 0.0153(15) 0.0026(13) 0.0020(11) 0.0046(13) C4 0.0191(15) 0.0195(19) 0.0140(14) -0.0006(13) 0.0011(11) -0.0030(12) C5 0.0151(15) 0.0201(19) 0.0192(15) 0.0017(14) 0.0009(12) 0.0025(13) C6 0.0164(14) 0.0190(19) 0.0200(15) 0.0025(13) 0.0023(12) 0.0055(13) O7 0.0137(10) 0.0227(14) 0.0249(12) -0.0007(9) 0.0060(8) -0.0027(10) O8 0.0169(11) 0.0262(15) 0.0248(12) -0.0039(11) 0.0004(9) -0.0013(10) Cl9 0.0225(4) 0.0238(5) 0.0201(4) -0.0019(3) 0.0031(3) -0.0039(3) O10 0.0135(11) 0.0284(15) 0.0237(12) -0.0011(10) 0.0058(9) -0.0044(10) O11 0.0163(11) 0.0276(15) 0.0233(11) -0.0046(10) 0.0026(9) -0.0032(10) Cl12 0.0193(4) 0.0200(5) 0.0187(4) 0.0004(3) 0.0029(3) -0.0019(3) C13 0.0204(16) 0.023(2) 0.0225(16) -0.0004(14) 0.0065(13) -0.0033(13) C14 0.0204(16) 0.026(2) 0.0252(17) -0.0019(15) 0.0012(13) -0.0012(15) C15 0.0202(16) 0.027(2) 0.0207(17) -0.0003(15) 0.0019(13) 0.0018(14) N16 0.0165(13) 0.0197(17) 0.0289(15) 0.0004(12) 0.0062(11) -0.0003(12) C17 0.0203(16) 0.032(2) 0.0241(17) -0.0073(16) 0.0017(13) -0.0039(15) C18 0.0245(17) 0.033(2) 0.0189(17) -0.0038(16) 0.0024(13) -0.0029(15) C19 0.0300(18) 0.021(2) 0.0270(17) -0.0049(15) 0.0114(14) 0.0007(14) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 C6 . 1.400(4) ? C1 C2 . 1.413(4) ? C1 Cl12 . 1.735(3) ? C2 O11 . 1.247(4) ? C2 C3 . 1.514(5) ? C3 O10 . 1.323(3) ? C3 C4 . 1.348(5) ? C4 C5 . 1.455(4) ? C4 Cl9 . 1.727(3) ? C5 O8 . 1.226(4) ? C5 C6 . 1.533(5) ? C6 O7 . 1.257(3) ? O10 H9 . 1.01(5) ? C13 C18 . 1.393(5) ? C13 C14 . 1.399(5) ? C13 C19 . 1.499(5) ? C14 C15 . 1.377(5) ? C14 H141 . 0.94(4) ? C15 N16 . 1.336(4) ? C15 H151 . 0.88(3) ? N16 C17 . 1.343(4) ? N16 H10 . 1.04(5) ? C17 C18 . 1.377(5) ? C17 H171 . 0.97(3) ? C18 H181 . 0.98(4) ? C19 H191 . 0.96 ? C19 H192 . 0.96 ? C19 H193 . 0.96 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 122.2(3) . . ? C6 C1 Cl12 119.4(2) . . ? C2 C1 Cl12 118.4(2) . . ? O11 C2 C1 125.8(3) . . ? O11 C2 C3 116.5(3) . . ? C1 C2 C3 117.7(3) . . ? O10 C3 C4 121.5(3) . . ? O10 C3 C2 115.8(3) . . ? C4 C3 C2 122.7(3) . . ? C3 C4 C5 120.0(3) . . ? C3 C4 Cl9 121.0(2) . . ? C5 C4 Cl9 118.9(2) . . ? O8 C5 C4 123.0(3) . . ? O8 C5 C6 118.5(3) . . ? C4 C5 C6 118.6(3) . . ? O7 C6 C1 125.1(3) . . ? O7 C6 C5 116.2(3) . . ? C1 C6 C5 118.7(3) . . ? C3 O10 H9 107(3) . . ? C18 C13 C14 117.4(3) . . ? C18 C13 C19 121.6(3) . . ? C14 C13 C19 121.0(3) . . ? C15 C14 C13 120.1(3) . . ? C15 C14 H141 118(2) . . ? C13 C14 H141 122(2) . . ? N16 C15 C14 120.5(3) . . ? N16 C15 H151 115(2) . . ? C14 C15 H151 124(2) . . ? C15 N16 C17 121.5(3) . . ? C15 N16 H10 119(2) . . ? C17 N16 H10 119(2) . . ? N16 C17 C18 120.0(3) . . ? N16 C17 H171 118(2) . . ? C18 C17 H171 122(2) . . ? C17 C18 C13 120.5(3) . . ? C17 C18 H181 121(2) . . ? C13 C18 H181 119(2) . . ? C13 C19 H191 109.5 . . ? C13 C19 H192 109.5 . . ? H191 C19 H192 109.5 . . ? C13 C19 H193 109.5 . . ? H191 C19 H193 109.5 . . ? H192 C19 H193 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O11 178.2(3) . . . . ? Cl12 C1 C2 O11 -0.1(5) . . . . ? C6 C1 C2 C3 -2.5(5) . . . . ? Cl12 C1 C2 C3 179.2(2) . . . . ? O11 C2 C3 O10 0.8(4) . . . . ? C1 C2 C3 O10 -178.6(3) . . . . ? O11 C2 C3 C4 -179.1(3) . . . . ? C1 C2 C3 C4 1.6(5) . . . . ? O10 C3 C4 C5 178.6(3) . . . . ? C2 C3 C4 C5 -1.6(5) . . . . ? O10 C3 C4 Cl9 0.4(5) . . . . ? C2 C3 C4 Cl9 -179.8(2) . . . . ? C3 C4 C5 O8 -177.6(3) . . . . ? Cl9 C4 C5 O8 0.6(5) . . . . ? C3 C4 C5 C6 2.4(5) . . . . ? Cl9 C4 C5 C6 -179.4(2) . . . . ? C2 C1 C6 O7 -177.0(3) . . . . ? Cl12 C1 C6 O7 1.3(5) . . . . ? C2 C1 C6 C5 3.4(5) . . . . ? Cl12 C1 C6 C5 -178.4(2) . . . . ? O8 C5 C6 O7 -2.9(4) . . . . ? C4 C5 C6 O7 177.1(3) . . . . ? O8 C5 C6 C1 176.8(3) . . . . ? C4 C5 C6 C1 -3.2(4) . . . . ? C18 C13 C14 C15 0.2(5) . . . . ? C19 C13 C14 C15 -178.1(3) . . . . ? C13 C14 C15 N16 0.5(5) . . . . ? C14 C15 N16 C17 -0.9(5) . . . . ? C15 N16 C17 C18 0.7(5) . . . . ? N16 C17 C18 C13 0.0(5) . . . . ? C14 C13 C18 C17 -0.5(5) . . . . ? C19 C13 C18 C17 177.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N16 H10 O7 1.04(5) 1.69(5) 2.686(4) 159(4) . N16 H10 O8 1.04(5) 2.36(4) 3.012(3) 120(3) . O10 H9 O11 1.01(5) 1.85(5) 2.665(3) 135(4) 3_667 _chemical_name_common '4-picoline chloranilate' # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment '4pic_2_1.cif' data_4pic_2_1_100K _database_code_depnum_ccdc_archive 'CCDC 737689' _chemical_name_systematic 'bis (4-picoline) chloranilate' _chemical_melting_point ? _cell_length_a 7.952(5) _cell_length_b 6.126(3) _cell_length_c 17.658(8) _cell_angle_alpha 90 _cell_angle_beta 96.73(3) _cell_angle_gamma 90 _cell_volume 854.2(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C9 H5.25 Cl1.50 N0.75 O3 # Dc = 1.75 Fooo = 408.00 Mu = 5.79 M = 225.07 # Found Formula = C9 H8 Cl1 N1 O2 # Dc = 1.54 FOOO = 408.00 Mu = 4.08 M = 197.62 _chemical_formula_sum 'C18 H16 Cl2 N2 O4' _chemical_formula_moiety '(C6 Cl2 O4), 2(C6 N1 H8)' _chemical_compound_source ? _chemical_formula_weight 395.24 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 100 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.408 # Sheldrick geometric approximatio 0.96 0.96 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9600 _exptl_absorpt_correction_T_max 0.9600 _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'WINGX (Farrugia, 1999)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 8250 _reflns_number_total 1869 _diffrn_reflns_av_R_equivalents 0.1101 # Number of reflections with Friedels Law is 1869 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1955 _diffrn_reflns_theta_min 3.263 _diffrn_reflns_theta_max 27.460 _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 26.087 _diffrn_measured_fraction_theta_full 0.966 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -9 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.499 _refine_diff_density_max 0.374 _refine_ls_number_reflns 1869 _refine_ls_number_restraints 0 _refine_ls_number_parameters 150 #_refine_ls_R_factor_ref 0.0931 _refine_ls_wR_factor_ref 0.1062 _refine_ls_goodness_of_fit_ref 1.049 #_reflns_number_all 1869 _refine_ls_R_factor_all 0.0986 _refine_ls_wR_factor_all 0.1062 _reflns_threshold_expression >2\s(I) _reflns_number_gt 1246 _refine_ls_R_factor_gt 0.0613 _refine_ls_shift/su_max 0.001 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+0.1683P] where P=(Fo^2^+2Fc^2^)/3' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.4257(5) -0.0673(5) 0.92403(17) 0.0240(8) Uani d . 1 . . C C2 0.5413(5) 0.1365(5) 0.93739(18) 0.0252(8) Uani d . 1 . . C C3 0.6095(5) 0.1867(5) 1.01208(18) 0.0238(8) Uani d . 1 . . C Cl1 0.73648(12) 0.41981(12) 1.02634(4) 0.0283(3) Uani d . 1 . . Cl O2 0.5641(3) 0.2436(4) 0.87893(12) 0.0276(6) Uani d . 1 . . O O1 0.3718(4) -0.1094(3) 0.85611(12) 0.0286(6) Uani d . 1 . . O C6 0.1039(5) 0.4916(5) 0.65415(19) 0.0269(8) Uani d . 1 . . C C7 0.1653(5) 0.5718(6) 0.72655(19) 0.0292(8) Uani d . 1 . . C C8 0.2743(5) 0.4472(6) 0.7746(2) 0.0312(9) Uani d . 1 . . C N1 0.3218(5) 0.2489(5) 0.75262(16) 0.0312(8) Uani d . 1 . . N C4 0.2670(5) 0.1654(6) 0.68369(19) 0.0294(9) Uani d . 1 . . C C5 0.1571(5) 0.2862(5) 0.6341(2) 0.0292(9) Uani d . 1 . . C C9 -0.0109(6) 0.6285(7) 0.5996(2) 0.0352(10) Uani d . 1 . . C H7 0.131(6) 0.711(7) 0.745(2) 0.050(13) Uiso d . 1 . . H H8 0.323(6) 0.483(6) 0.822(2) 0.047(12) Uiso d . 1 . . H H4 0.306(4) 0.022(5) 0.6690(18) 0.018(8) Uiso d . 1 . . H H5 0.115(6) 0.231(6) 0.585(2) 0.043(11) Uiso d . 1 . . H H91 -0.059(7) 0.750(8) 0.632(3) 0.064(15) Uiso d . 1 . . H H93 0.054(6) 0.701(6) 0.570(2) 0.034(11) Uiso d . 1 . . H H92 -0.086(7) 0.539(7) 0.566(3) 0.063(14) Uiso d . 1 . . H H1 0.395(7) 0.177(8) 0.788(3) 0.066(15) Uiso d . 1 . . H 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 0.027(2) 0.0205(15) 0.0238(17) 0.0031(14) 0.0001(14) 0.0017(12) C2 0.025(2) 0.0262(17) 0.0235(17) 0.0073(14) 0.0012(14) 0.0023(12) C3 0.025(2) 0.0176(16) 0.0282(18) -0.0020(13) 0.0003(14) -0.0027(12) Cl1 0.0331(6) 0.0243(5) 0.0269(4) -0.0042(3) 0.0009(3) -0.0011(3) O2 0.0330(18) 0.0274(12) 0.0220(12) -0.0003(10) 0.0017(10) 0.0045(9) O1 0.0377(18) 0.0284(12) 0.0185(12) 0.0002(10) -0.0017(10) 0.0003(9) C6 0.024(2) 0.0283(17) 0.0287(18) -0.0036(14) 0.0063(14) 0.0033(13) C7 0.034(3) 0.0275(18) 0.0263(18) 0.0001(16) 0.0055(15) -0.0017(14) C8 0.036(3) 0.0340(19) 0.0227(18) -0.0037(16) 0.0012(15) -0.0021(14) N1 0.035(2) 0.0352(16) 0.0226(15) 0.0061(14) 0.0022(13) 0.0044(12) C4 0.037(3) 0.0242(17) 0.0278(18) 0.0025(16) 0.0055(15) -0.0015(13) C5 0.034(3) 0.0301(19) 0.0224(17) -0.0012(15) -0.0004(15) -0.0024(14) C9 0.036(3) 0.037(2) 0.031(2) 0.0012(18) 0.0017(18) 0.0087(17) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 O1 . 1.252(4) ? C1 C3 3_657 1.400(5) ? C1 C2 . 1.553(5) ? C2 O2 . 1.254(4) ? C2 C3 . 1.400(5) ? C3 C1 3_657 1.400(5) ? C3 Cl1 . 1.750(3) ? C6 C5 . 1.387(5) ? C6 C7 . 1.403(5) ? C6 C9 . 1.502(5) ? C7 C8 . 1.371(5) ? C7 H7 . 0.96(4) ? C8 N1 . 1.343(5) ? C8 H8 . 0.91(4) ? N1 C4 . 1.345(4) ? N1 H1 . 0.91(5) ? C4 C5 . 1.378(5) ? C4 H4 . 0.97(3) ? C5 H5 . 0.96(4) ? C9 H91 . 1.04(5) ? C9 H93 . 0.89(4) ? C9 H92 . 0.96(5) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C3 125.9(3) . 3_657 ? O1 C1 C2 116.2(3) . . ? C3 C1 C2 117.9(3) 3_657 . ? O2 C2 C3 125.7(3) . . ? O2 C2 C1 115.8(3) . . ? C3 C2 C1 118.5(3) . . ? C2 C3 C1 123.5(3) . 3_657 ? C2 C3 Cl1 117.9(3) . . ? C1 C3 Cl1 118.5(2) 3_657 . ? C5 C6 C7 117.8(3) . . ? C5 C6 C9 121.5(3) . . ? C7 C6 C9 120.6(3) . . ? C8 C7 C6 119.7(3) . . ? C8 C7 H7 117(2) . . ? C6 C7 H7 123(2) . . ? N1 C8 C7 120.3(3) . . ? N1 C8 H8 112(3) . . ? C7 C8 H8 127(3) . . ? C8 N1 C4 122.2(3) . . ? C8 N1 H1 115(3) . . ? C4 N1 H1 123(3) . . ? N1 C4 C5 119.1(3) . . ? N1 C4 H4 120.3(18) . . ? C5 C4 H4 120.7(18) . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 121(2) . . ? C6 C5 H5 118(2) . . ? C6 C9 H91 106(2) . . ? C6 C9 H93 107(3) . . ? H91 C9 H93 104(4) . . ? C6 C9 H92 111(3) . . ? H91 C9 H92 120(4) . . ? H93 C9 H92 107(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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 2.6(5) . . . . ? C3 C1 C2 O2 -177.3(3) 3_657 . . . ? O1 C1 C2 C3 -177.9(3) . . . . ? C3 C1 C2 C3 2.2(5) 3_657 . . . ? O2 C2 C3 C1 177.1(4) . . . 3_657 ? C1 C2 C3 C1 -2.3(6) . . . 3_657 ? O2 C2 C3 Cl1 0.5(5) . . . . ? C1 C2 C3 Cl1 -178.9(2) . . . . ? C5 C6 C7 C8 0.1(6) . . . . ? C9 C6 C7 C8 -177.9(4) . . . . ? C6 C7 C8 N1 -0.3(6) . . . . ? C7 C8 N1 C4 0.6(6) . . . . ? C8 N1 C4 C5 -0.7(6) . . . . ? N1 C4 C5 C6 0.5(6) . . . . ? C7 C6 C5 C4 -0.2(6) . . . . ? C9 C6 C5 C4 177.8(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.91(5) 2.15(5) 2.854(4) 133(4) . N1 H1 O2 0.91(5) 2.01(5) 2.771(4) 139(4) . _chemical_name_common 'bis (4-picoline) chloranilate' data_4pic_2_1_200K _database_code_depnum_ccdc_archive 'CCDC 737690' _chemical_name_systematic 'bis (4-picoline) chloranilate' _chemical_melting_point ? _cell_length_a 8.037(5) _cell_length_b 6.099(3) _cell_length_c 17.679(8) _cell_angle_alpha 90 _cell_angle_beta 96.56(3) _cell_angle_gamma 90 _cell_volume 861.0(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C9 H5.25 Cl1.50 N0.75 O3 # Dc = 1.74 Fooo = 408.00 Mu = 5.74 M = 225.07 # Found Formula = C9 H8 Cl1 N1 O2 # Dc = 1.52 FOOO = 408.00 Mu = 4.05 M = 197.62 _chemical_formula_sum 'C18 H16 Cl2 N2 O4' _chemical_formula_moiety '(C6 Cl2 O4), 2(C6 N1 H8)' _chemical_compound_source ? _chemical_formula_weight 395.24 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 200 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.405 # Sheldrick geometric approximatio 0.92 0.92 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9222 _exptl_absorpt_correction_T_max 0.9222 _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'WINGX (Farrugia, 1999)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 8229 _reflns_number_total 1916 _diffrn_reflns_av_R_equivalents 0.0613 # Number of reflections with Friedels Law is 1916 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1971 _diffrn_reflns_theta_min 3.246 _diffrn_reflns_theta_max 27.464 _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.816 _diffrn_measured_fraction_theta_full 0.977 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.275 _refine_diff_density_max 0.247 _refine_ls_number_reflns 1916 _refine_ls_number_restraints 0 _refine_ls_number_parameters 150 #_refine_ls_R_factor_ref 0.0750 _refine_ls_wR_factor_ref 0.0539 _refine_ls_goodness_of_fit_ref 1.045 #_reflns_number_all 1916 _refine_ls_R_factor_all 0.0758 _refine_ls_wR_factor_all 0.0539 _reflns_threshold_expression >2\s(I) _reflns_number_gt 1315 _refine_ls_R_factor_gt 0.0437 _refine_ls_shift/su_max 0 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+0.4476P] where P=(Fo^2^+2Fc^2^)/3' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.4256(3) -0.0657(4) 0.92443(12) 0.0269(5) Uani d . 1 . . C C2 0.5414(3) 0.1370(3) 0.93742(12) 0.0268(5) Uani d . 1 . . C C3 0.6101(3) 0.1848(3) 1.01168(13) 0.0280(5) Uani d . 1 . . C Cl1 0.73784(9) 0.41563(10) 1.02586(3) 0.0373(2) Uani d . 1 . . Cl O2 0.5642(2) 0.2438(3) 0.87939(9) 0.0345(4) Uani d . 1 . . O O1 0.3713(2) -0.1073(3) 0.85698(9) 0.0361(5) Uani d . 1 . . O C6 0.1078(3) 0.4924(4) 0.65602(13) 0.0314(6) Uani d . 1 . . C C7 0.1676(4) 0.5701(4) 0.72785(14) 0.0357(6) Uani d . 1 . . C C8 0.2745(4) 0.4469(4) 0.77542(14) 0.0385(6) Uani d . 1 . . C N1 0.3235(3) 0.2488(4) 0.75360(12) 0.0377(5) Uani d . 1 . . N C4 0.2701(4) 0.1676(4) 0.68460(14) 0.0375(6) Uani d . 1 . . C C5 0.1628(4) 0.2874(4) 0.63540(14) 0.0357(6) Uani d . 1 . . C C9 -0.0068(4) 0.6287(5) 0.60225(18) 0.0455(7) Uani d . 1 . . C H7 0.133(3) 0.700(4) 0.7451(14) 0.041(7) Uiso d . 1 . . H H8 0.321(3) 0.489(4) 0.8241(14) 0.037(7) Uiso d . 1 . . H H4 0.313(3) 0.021(4) 0.6718(14) 0.043(7) Uiso d . 1 . . H H5 0.124(4) 0.229(4) 0.5871(15) 0.048(8) Uiso d . 1 . . H H91 -0.052(5) 0.757(7) 0.629(2) 0.115(15) Uiso d . 1 . . H H93 0.056(5) 0.690(6) 0.565(2) 0.077(11) Uiso d . 1 . . H H92 -0.083(5) 0.543(6) 0.572(2) 0.094(13) Uiso d . 1 . . H H1 0.396(5) 0.166(5) 0.790(2) 0.083(11) Uiso d . 1 . . H 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 0.0288(15) 0.0259(11) 0.0259(12) 0.0060(10) 0.0032(9) -0.0010(9) C2 0.0270(15) 0.0260(11) 0.0279(12) 0.0076(9) 0.0059(10) 0.0012(9) C3 0.0276(15) 0.0253(11) 0.0311(12) -0.0006(10) 0.0038(10) 0.0003(9) Cl1 0.0428(4) 0.0321(3) 0.0369(3) -0.0082(3) 0.0042(3) -0.0024(2) O2 0.0392(12) 0.0360(9) 0.0287(9) -0.0017(8) 0.0057(7) 0.0078(7) O1 0.0471(13) 0.0352(9) 0.0249(9) -0.0019(8) -0.0007(7) -0.0019(7) C6 0.0277(16) 0.0355(12) 0.0316(12) -0.0030(10) 0.0067(10) 0.0023(10) C7 0.0428(18) 0.0310(13) 0.0349(13) 0.0008(12) 0.0122(11) -0.0037(11) C8 0.0442(18) 0.0477(16) 0.0240(13) -0.0055(13) 0.0052(11) -0.0045(11) N1 0.0416(16) 0.0406(12) 0.0312(11) 0.0070(10) 0.0055(10) 0.0049(9) C4 0.0449(19) 0.0330(14) 0.0359(14) 0.0039(12) 0.0105(12) -0.0018(11) C5 0.0397(18) 0.0403(14) 0.0271(13) -0.0013(12) 0.0032(11) -0.0054(11) C9 0.039(2) 0.0521(18) 0.0447(17) 0.0059(14) 0.0030(14) 0.0136(14) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 O1 . 1.248(3) ? C1 C3 3_657 1.400(3) ? C1 C2 . 1.549(3) ? C2 O2 . 1.246(3) ? C2 C3 . 1.396(3) ? C3 C1 3_657 1.400(3) ? C3 Cl1 . 1.744(2) ? C6 C5 . 1.389(4) ? C6 C7 . 1.389(3) ? C6 C9 . 1.498(4) ? C7 C8 . 1.358(4) ? C7 H7 . 0.91(3) ? C8 N1 . 1.341(3) ? C8 H8 . 0.93(2) ? N1 C4 . 1.341(3) ? N1 H1 . 0.96(3) ? C4 C5 . 1.365(4) ? C4 H4 . 0.99(3) ? C5 H5 . 0.95(3) ? C9 H91 . 1.01(4) ? C9 H93 . 0.95(4) ? C9 H92 . 0.92(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C3 125.7(2) . 3_657 ? O1 C1 C2 116.3(2) . . ? C3 C1 C2 118.00(19) 3_657 . ? O2 C2 C3 125.9(2) . . ? O2 C2 C1 115.95(19) . . ? C3 C2 C1 118.2(2) . . ? C2 C3 C1 123.7(2) . 3_657 ? C2 C3 Cl1 117.83(17) . . ? C1 C3 Cl1 118.32(17) 3_657 . ? C5 C6 C7 117.4(2) . . ? C5 C6 C9 121.6(2) . . ? C7 C6 C9 121.0(2) . . ? C8 C7 C6 120.4(2) . . ? C8 C7 H7 118.3(16) . . ? C6 C7 H7 121.3(16) . . ? N1 C8 C7 120.4(2) . . ? N1 C8 H8 114.4(15) . . ? C7 C8 H8 125.2(16) . . ? C4 N1 C8 121.4(2) . . ? C4 N1 H1 121(2) . . ? C8 N1 H1 117(2) . . ? N1 C4 C5 119.7(2) . . ? N1 C4 H4 117.2(14) . . ? C5 C4 H4 123.1(14) . . ? C4 C5 C6 120.7(2) . . ? C4 C5 H5 119.4(16) . . ? C6 C5 H5 119.8(16) . . ? C6 C9 H91 111(2) . . ? C6 C9 H93 108(2) . . ? H91 C9 H93 106(3) . . ? C6 C9 H92 111(2) . . ? H91 C9 H92 118(3) . . ? H93 C9 H92 102(3) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 2.5(3) . . . . ? C3 C1 C2 O2 -177.1(2) 3_657 . . . ? O1 C1 C2 C3 -177.6(2) . . . . ? C3 C1 C2 C3 2.8(4) 3_657 . . . ? O2 C2 C3 C1 176.9(2) . . . 3_657 ? C1 C2 C3 C1 -3.0(4) . . . 3_657 ? O2 C2 C3 Cl1 0.8(3) . . . . ? C1 C2 C3 Cl1 -179.08(16) . . . . ? C5 C6 C7 C8 -0.5(4) . . . . ? C9 C6 C7 C8 -178.5(3) . . . . ? C6 C7 C8 N1 0.0(4) . . . . ? C7 C8 N1 C4 0.5(4) . . . . ? C8 N1 C4 C5 -0.4(4) . . . . ? N1 C4 C5 C6 -0.1(4) . . . . ? C7 C6 C5 C4 0.6(4) . . . . ? C9 C6 C5 C4 178.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.96(3) 2.06(3) 2.836(3) 136(3) . N1 H1 O2 0.96(3) 2.01(3) 2.776(3) 135(3) . _chemical_name_common 'bis (4-picoline) chloranilate' data_4pic_2_1_300K _database_code_depnum_ccdc_archive 'CCDC 737691' _chemical_name_systematic 'bis (4-picoline) chloranilate' _chemical_melting_point ? _cell_length_a 8.192(5) _cell_length_b 6.099(2) _cell_length_c 17.721(9) _cell_angle_alpha 90 _cell_angle_beta 96.259(19) _cell_angle_gamma 90 _cell_volume 880.1(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C9 H5.25 Cl1.50 N0.75 O3 # Dc = 1.70 Fooo = 408.00 Mu = 5.62 M = 225.07 # Found Formula = C9 H8 Cl1 N1 O2 # Dc = 1.49 FOOO = 408.00 Mu = 3.96 M = 197.62 _chemical_formula_sum 'C18 H16 Cl2 N2 O4' _chemical_formula_moiety '(C6 Cl2 O4), 2(C6 N1 H8)' _chemical_compound_source ? _chemical_formula_weight 395.24 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 300 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.396 # Sheldrick geometric approximatio 0.96 0.96 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9612 _exptl_absorpt_correction_T_max 0.9612 _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'WINGX, (Farrugia, 1999)' _computing_publication_material 'WINGX, (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 300 _diffrn_reflns_number 8757 _reflns_number_total 1954 _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_theta_min 3.217 _diffrn_reflns_theta_max 27.475 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.277 _diffrn_measured_fraction_theta_full 0.976 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.22 _refine_diff_density_max 0.223 _refine_ls_number_reflns 1954 _refine_ls_number_restraints 0 _refine_ls_number_parameters 150 #_refine_ls_R_factor_ref 0.0978 _refine_ls_wR_factor_ref 0.0844 _refine_ls_goodness_of_fit_ref 0.992 #_reflns_number_all 1950 _refine_ls_R_factor_all 0.0997 _refine_ls_wR_factor_all 0.0844 _reflns_threshold_expression >2\s(I) _reflns_number_gt 779 _refine_ls_R_factor_gt 0.0446 _refine_ls_shift/su_max 0.001 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.4250(3) -0.0642(3) 0.92506(13) 0.0409(6) Uani d . 1 . . C C2 0.5407(3) 0.1365(4) 0.93728(13) 0.0409(6) Uani d . 1 . . C C3 0.6101(3) 0.1829(3) 1.01129(13) 0.0413(6) Uani d . 1 . . C Cl1 0.73798(10) 0.41166(10) 1.02505(4) 0.0569(3) Uani d . 1 . . Cl O2 0.5632(2) 0.2433(3) 0.87927(9) 0.0529(5) Uani d . 1 . . O O1 0.3702(2) -0.1041(2) 0.85763(9) 0.0546(5) Uani d . 1 . . O C6 0.1105(3) 0.4918(4) 0.65702(14) 0.0461(6) Uani d . 1 . . C C7 0.1689(4) 0.5688(4) 0.72869(15) 0.0528(7) Uani d . 1 . . C C8 0.2750(4) 0.4486(5) 0.77576(16) 0.0563(8) Uani d . 1 . . C N1 0.3247(3) 0.2523(4) 0.75349(13) 0.0570(6) Uani d . 1 . . N C4 0.2727(4) 0.1718(5) 0.68508(16) 0.0570(8) Uani d . 1 . . C C5 0.1663(4) 0.2881(4) 0.63649(15) 0.0525(7) Uani d . 1 . . C C9 -0.0050(5) 0.6277(7) 0.6046(2) 0.0739(10) Uani d . 1 . . C H7 0.139(4) 0.693(5) 0.7459(16) 0.073(10) Uiso d . 1 . . H H8 0.318(4) 0.493(4) 0.8239(17) 0.073(9) Uiso d . 1 . . H H4 0.306(3) 0.035(4) 0.6711(15) 0.062(8) Uiso d . 1 . . H H5 0.131(4) 0.229(4) 0.5861(16) 0.072(9) Uiso d . 1 . . H H91 -0.039(6) 0.769(9) 0.635(3) 0.17(2) Uiso d . 1 . . H H93 0.053(5) 0.689(6) 0.569(2) 0.106(14) Uiso d . 1 . . H H92 -0.073(6) 0.545(7) 0.580(3) 0.14(2) Uiso d . 1 . . H H1 0.393(4) 0.181(5) 0.7885(18) 0.088(11) Uiso d . 1 . . H 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 0.0460(17) 0.0396(12) 0.0367(14) 0.0069(11) 0.0028(11) 0.0017(10) C2 0.0428(17) 0.0419(13) 0.0391(14) 0.0102(10) 0.0093(11) 0.0029(10) C3 0.0438(17) 0.0361(12) 0.0437(14) 0.0017(11) 0.0036(12) 0.0002(10) Cl1 0.0663(6) 0.0483(4) 0.0563(4) -0.0124(3) 0.0082(3) -0.0025(3) O2 0.0620(15) 0.0560(10) 0.0419(10) -0.0032(9) 0.0108(9) 0.0125(8) O1 0.0737(15) 0.0500(9) 0.0388(10) -0.0030(9) -0.0005(9) -0.0021(7) C6 0.0421(17) 0.0515(13) 0.0459(14) -0.0024(12) 0.0099(12) 0.0044(11) C7 0.062(2) 0.0445(15) 0.0536(17) 0.0019(14) 0.0156(14) -0.0051(13) C8 0.069(2) 0.0602(17) 0.0406(15) -0.0026(15) 0.0079(14) -0.0071(13) N1 0.0620(18) 0.0640(14) 0.0453(13) 0.0101(12) 0.0077(12) 0.0072(12) C4 0.073(2) 0.0465(15) 0.0534(17) 0.0075(15) 0.0158(15) -0.0054(13) C5 0.061(2) 0.0542(16) 0.0426(15) -0.0013(13) 0.0063(14) -0.0091(12) C9 0.062(3) 0.086(3) 0.073(2) 0.011(2) 0.004(2) 0.017(2) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 O1 . 1.254(3) ? C1 C3 3_657 1.396(3) ? C1 C2 . 1.548(4) ? C2 O2 . 1.248(3) ? C2 C3 . 1.400(3) ? C3 C1 3_657 1.396(3) ? C3 Cl1 . 1.746(2) ? C6 C5 . 1.386(4) ? C6 C7 . 1.389(4) ? C6 C9 . 1.501(4) ? C7 C8 . 1.353(4) ? C7 H7 . 0.86(3) ? C8 N1 . 1.338(3) ? C8 H8 . 0.93(3) ? N1 C4 . 1.334(4) ? N1 H1 . 0.90(3) ? C4 C5 . 1.357(4) ? C4 H4 . 0.92(3) ? C5 H5 . 0.98(3) ? C9 H91 . 1.07(5) ? C9 H93 . 0.91(4) ? C9 H92 . 0.84(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C3 125.8(2) . 3_657 ? O1 C1 C2 115.9(2) . . ? C3 C1 C2 118.3(2) 3_657 . ? O2 C2 C3 125.8(2) . . ? O2 C2 C1 116.2(2) . . ? C3 C2 C1 118.1(2) . . ? C1 C3 C2 123.6(2) 3_657 . ? C1 C3 Cl1 118.34(18) 3_657 . ? C2 C3 Cl1 117.95(18) . . ? C5 C6 C7 116.9(2) . . ? C5 C6 C9 122.4(3) . . ? C7 C6 C9 120.7(3) . . ? C8 C7 C6 121.0(3) . . ? C8 C7 H7 116(2) . . ? C6 C7 H7 123(2) . . ? N1 C8 C7 119.9(3) . . ? N1 C8 H8 115.8(17) . . ? C7 C8 H8 124.3(18) . . ? C4 N1 C8 121.4(3) . . ? C4 N1 H1 124(2) . . ? C8 N1 H1 115(2) . . ? N1 C4 C5 120.2(3) . . ? N1 C4 H4 120.2(16) . . ? C5 C4 H4 119.5(16) . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.7(16) . . ? C6 C5 H5 119.6(16) . . ? C6 C9 H91 108(3) . . ? C6 C9 H93 108(3) . . ? H91 C9 H93 102(3) . . ? C6 C9 H92 109(3) . . ? H91 C9 H92 124(4) . . ? H93 C9 H92 105(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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 2.5(3) . . . . ? C3 C1 C2 O2 -177.1(2) 3_657 . . . ? O1 C1 C2 C3 -177.6(2) . . . . ? C3 C1 C2 C3 2.8(4) 3_657 . . . ? O2 C2 C3 C1 176.9(2) . . . 3_657 ? C1 C2 C3 C1 -2.9(4) . . . 3_657 ? O2 C2 C3 Cl1 0.8(4) . . . . ? C1 C2 C3 Cl1 -179.06(17) . . . . ? C5 C6 C7 C8 -0.1(4) . . . . ? C9 C6 C7 C8 -178.9(3) . . . . ? C6 C7 C8 N1 -0.2(5) . . . . ? C7 C8 N1 C4 0.6(5) . . . . ? C8 N1 C4 C5 -0.5(5) . . . . ? N1 C4 C5 C6 0.1(5) . . . . ? C7 C6 C5 C4 0.2(4) . . . . ? C9 C6 C5 C4 179.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.90(3) 2.15(3) 2.849(3) 134(3) . N1 H1 O2 0.90(3) 2.05(3) 2.800(3) 140(3) . _chemical_name_common 'bis (4-picoline) chloranilate' # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment '4pic_2_1_hydrate_100.cif' data_4pic_2_1_hydrate_100 _database_code_depnum_ccdc_archive 'CCDC 737692' _audit_creation_date 09-10-06 _audit_creation_method CRYSTALS_ver_12.85 _chemical_name_systematic 'bis(4-picoline) chloranilate tetrahydrate' _chemical_melting_point ? _cell_length_a 7.268(9) _cell_length_b 8.957(9) _cell_length_c 16.925(18) _cell_angle_alpha 90 _cell_angle_beta 98.20(4) _cell_angle_gamma 90 _cell_volume 1091(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall ? 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 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C10 H10 Cl1 N1 O1 # Dc = 1.19 Fooo = 488.00 Mu = 3.12 M = 195.65 # Found Formula = C9 H12 Cl1 N1 O4 # Dc = 1.42 FOOO = 488.00 Mu = 3.44 M = 233.65 _chemical_formula_sum 'C18 H24 Cl2 N2 O8' _chemical_formula_moiety '(C6 Cl2 O4) 2(C6 N1 H8) 4(H2 O)' _chemical_compound_source ? _chemical_formula_weight 467.30 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 100 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_min ? _exptl_crystal_size_mid ? _exptl_crystal_size_max ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.344 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_T_max 1.0000 _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 5793 _reflns_number_total 2435 _diffrn_reflns_av_R_equivalents 0.063 # Number of reflections with Friedels Law is 2435 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1651 _diffrn_reflns_theta_min 3.237 _diffrn_reflns_theta_max 27.362 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.994 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _oxford_diffrn_Wilson_B_factor 1.85 _oxford_diffrn_Wilson_scale 0.18 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.95 _refine_diff_density_max 0.85 _refine_ls_number_reflns 1625 _refine_ls_number_restraints 0 _refine_ls_number_parameters 137 #_refine_ls_R_factor_ref 0.1171 _refine_ls_wR_factor_ref 0.1592 _refine_ls_goodness_of_fit_ref 0.9457 #_reflns_number_all 1625 _refine_ls_R_factor_all 0.1174 _refine_ls_wR_factor_all 0.1592 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 920 _refine_ls_R_factor_gt 0.0668 _refine_ls_wR_factor_gt 0.1405 _refine_ls_shift/su_max 0.000322 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _exptl_special_details ; The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98 \%A) and U~iso~(H) (in the range 1.2-1.5 times the U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.00P)^2^ + 5.63P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C 0.4402(8) 0.3588(7) 0.5293(4) 0.0214 1.0000 Uani . . . . . . . C2 C 0.4509(8) 0.3826(7) 0.4405(4) 0.0228 1.0000 Uani . . . . . . . C3 C 0.4928(8) 0.4755(7) 0.5834(3) 0.0195 1.0000 Uani . . . . . . . Cl4 Cl 0.4877(2) 0.44354(18) 0.68483(9) 0.0244 1.0000 Uani . . . . . . . O5 O 0.4098(6) 0.2747(4) 0.3941(2) 0.0237 1.0000 Uani . . . . . . . O6 O 0.3844(6) 0.2311(5) 0.5485(2) 0.0237 1.0000 Uani . . . . . . . C7 C 0.1084(8) -0.2713(7) 0.4029(4) 0.0251 1.0000 Uani . . . . . . . C8 C 0.1316(8) -0.2194(7) 0.4822(4) 0.0249 1.0000 Uani . . . . . . . C9 C 0.2095(8) -0.0806(7) 0.4992(4) 0.0247 1.0000 Uani . . . . . . . N10 N 0.2641(7) 0.0038(6) 0.4413(3) 0.0246 1.0000 Uani . . . . . . . C11 C 0.2450(9) -0.0438(7) 0.3654(4) 0.0272 1.0000 Uani . . . . . . . C12 C 0.1687(9) -0.1798(7) 0.3455(4) 0.0292 1.0000 Uani . . . . . . . C13 C 0.0221(9) -0.4230(7) 0.3815(4) 0.0340 1.0000 Uani . . . . . . . O14 O 0.2695(7) -0.2200(5) 0.6873(3) 0.0378 1.0000 Uani . . . . . . . O15 O 0.3215(7) 0.0875(5) 0.6921(3) 0.0372 1.0000 Uani . . . . . . . H81 H 0.0908 -0.2765 0.5222 0.0300 1.0000 Uiso R . . . . . . H91 H 0.2238 -0.0425 0.5510 0.0295 1.0000 Uiso R . . . . . . H111 H 0.2881 0.0167 0.3268 0.0316 1.0000 Uiso R . . . . . . H121 H 0.1570 -0.2115 0.2923 0.0339 1.0000 Uiso R . . . . . . H131 H 0.0893 -0.4737 0.3445 0.0502 1.0000 Uiso R . . . . . . H132 H 0.0244 -0.4832 0.4288 0.0502 1.0000 Uiso R . . . . . . H133 H -0.1050 -0.4117 0.3571 0.0503 1.0000 Uiso R . . . . . . H151 H 0.3498 0.1469 0.6584 0.0583 1.0000 Uiso . . . . . . . H101 H 0.3129 0.0894 0.4528 0.0303 1.0000 Uiso R . . . . . . H152 H 0.2774 0.1480 0.7205 0.0587 1.0000 Uiso R . . . . . . H141 H 0.3726 -0.2444 0.6772 0.0591 1.0000 Uiso R . . . . . . H142 H 0.2778 -0.1288 0.6851 0.0595 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.021(4) 0.022(4) 0.022(4) 0.009(3) 0.005(3) 0.003(3) C2 0.017(3) 0.027(4) 0.026(4) 0.006(3) 0.004(3) 0.007(3) C3 0.020(4) 0.026(4) 0.013(3) 0.005(3) 0.003(3) 0.001(3) Cl4 0.0298(9) 0.0217(9) 0.0221(8) 0.0003(7) 0.0053(7) -0.0018(8) O5 0.032(3) 0.015(2) 0.025(3) -0.008(2) 0.006(2) -0.002(2) O6 0.026(3) 0.017(2) 0.028(3) 0.004(2) 0.007(2) -0.002(2) C7 0.015(3) 0.019(4) 0.040(4) -0.004(3) 0.000(3) 0.000(3) C8 0.021(4) 0.020(4) 0.035(4) -0.001(3) 0.008(3) -0.003(3) C9 0.020(4) 0.030(4) 0.025(4) -0.004(3) 0.008(3) 0.002(3) N10 0.024(3) 0.015(3) 0.036(3) -0.008(3) 0.005(3) -0.002(2) C11 0.031(4) 0.026(4) 0.023(4) -0.005(3) 0.000(3) -0.007(3) C12 0.023(4) 0.026(4) 0.037(4) -0.006(3) -0.003(3) 0.000(3) C13 0.030(4) 0.013(4) 0.057(5) -0.007(3) -0.001(3) -0.001(3) O14 0.046(3) 0.022(3) 0.049(3) 0.005(2) 0.020(2) 0.006(2) O15 0.059(3) 0.018(3) 0.040(3) 0.003(2) 0.026(3) 0.000(2) _refine_ls_extinction_coef 28(15) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 2.20(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.531(9) yes C1 . C3 . 1.405(9) yes C1 . O6 . 1.272(7) yes C2 . C3 2_666 1.412(8) yes C2 . O5 . 1.255(7) yes C3 . Cl4 . 1.746(6) yes C7 . C8 . 1.408(9) yes C7 . C12 . 1.389(9) yes C7 . C13 . 1.518(8) yes C8 . C9 . 1.380(8) yes C8 . H81 . 0.931 no C9 . N10 . 1.342(8) yes C9 . H91 . 0.933 no N10 . C11 . 1.341(8) yes N10 . H101 . 0.855 no C11 . C12 . 1.361(9) yes C11 . H111 . 0.936 no C12 . H121 . 0.936 no C13 . H131 . 0.961 no C13 . H132 . 0.964 no C13 . H133 . 0.963 no O14 . H141 . 0.822 no O14 . H142 . 0.820 no O15 . H151 . 0.827 no O15 . H152 . 0.820 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C3 . 119.2(6) yes C2 . C1 . O6 . 116.0(6) yes C3 . C1 . O6 . 124.7(6) yes C1 . C2 . C3 2_666 117.6(6) yes C1 . C2 . O5 . 117.9(6) yes C3 2_666 C2 . O5 . 124.5(6) yes C2 2_666 C3 . C1 . 123.1(5) yes C2 2_666 C3 . Cl4 . 118.5(5) yes C1 . C3 . Cl4 . 118.4(5) yes C8 . C7 . C12 . 117.7(6) yes C8 . C7 . C13 . 120.8(6) yes C12 . C7 . C13 . 121.5(6) yes C7 . C8 . C9 . 119.1(6) yes C7 . C8 . H81 . 120.4 no C9 . C8 . H81 . 120.4 no C8 . C9 . N10 . 120.7(6) yes C8 . C9 . H91 . 120.9 no N10 . C9 . H91 . 118.4 no C9 . N10 . C11 . 121.3(5) yes C9 . N10 . H101 . 119.7 no C11 . N10 . H101 . 119.0 no N10 . C11 . C12 . 120.3(6) yes N10 . C11 . H111 . 119.0 no C12 . C11 . H111 . 120.6 no C7 . C12 . C11 . 120.8(6) yes C7 . C12 . H121 . 119.9 no C11 . C12 . H121 . 119.3 no C7 . C13 . H131 . 110.3 no C7 . C13 . H132 . 110.2 no H131 . C13 . H132 . 109.1 no C7 . C13 . H133 . 110.3 no H131 . C13 . H133 . 108.4 no H132 . C13 . H133 . 108.5 no H141 . O14 . H142 . 100.3 no H151 . O15 . H152 . 97.8 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag O15 . H151 . O6 . 159 0.83 2.05 2.843(9) yes N10 . H101 . O5 . 139 0.86 2.11 2.809(9) yes N10 . H101 . O6 . 141 0.86 2.07 2.784(9) yes O15 . H152 . O14 3_556 164 0.82 2.02 2.822(9) yes O14 . H141 . O5 2_656 157 0.82 2.14 2.914(9) yes O14 . H142 . O15 . 173 0.82 1.96 2.779(9) yes _chemical_name_common 'bis(4-picoline) chloranilate tetrahydrate' # Attachment '1to1Chl2pic.cif' data_2pic_1_1_100K _database_code_depnum_ccdc_archive 'CCDC 744784' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_formula_moiety '(C6 Cl2 O4 H), (C6 H8 N)' _chemical_formula_sum 'C12 H9 Cl2 N O4' _chemical_formula_weight 302.1 _chemical_absolute_configuration . #============================================================================== # CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3752(15) _cell_length_b 9.1468(18) _cell_length_c 9.7296(19) _cell_angle_alpha 101.63(3) _cell_angle_beta 103.92(3) _cell_angle_gamma 97.45(3) _cell_volume 612.9(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 100(2) _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.637 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.538 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_measurement_method \w _diffrn_reflns_number 15869 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_unetI/netI 0.0296 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 35.1 _diffrn_reflns_theta_full 35.1 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measured_fraction_theta_full 0.981 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number 0 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 5333 _reflns_number_gt 4848 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_all 0.08 _refine_ls_wR_factor_ref 0.0849 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_number_reflns 5333 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.1622P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.6 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.06 _refine_ls_extinction_method none 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'WINGX (Farrugia, 1999)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.27351(11) 0.60092(8) 1.06437(8) 0.01228(12) Uani d . 1 . . C C2 0.24363(10) 0.45480(8) 0.96129(8) 0.01231(12) Uani d . 1 . . C C3 0.28409(10) 0.45186(8) 0.81180(8) 0.01181(12) Uani d . 1 . . C C4 0.35018(11) 0.59072(8) 0.78381(8) 0.01154(12) Uani d . 1 . . C C5 0.38667(10) 0.72994(8) 0.88764(8) 0.01109(11) Uani d . 1 . . C C6 0.34380(11) 0.72986(8) 1.03167(8) 0.01165(12) Uani d . 1 . . C O7 0.37953(10) 0.86443(7) 1.12484(7) 0.01606(11) Uani d . 1 . . O O8 0.45201(9) 0.85668(6) 0.87204(6) 0.01513(11) Uani d . 1 . . O Cl9 0.39963(3) 0.59112(2) 0.61891(2) 0.01461(5) Uani d . 1 . . Cl O10 0.25650(9) 0.32451(6) 0.72582(7) 0.01612(11) Uani d . 1 . . O O11 0.19085(10) 0.33382(7) 0.98764(7) 0.01796(12) Uani d . 1 . . O Cl12 0.22641(3) 0.60548(2) 1.22997(2) 0.01729(5) Uani d . 1 . . Cl C13 0.14633(11) -0.06433(8) 0.62987(8) 0.01246(12) Uani d . 1 . . C N14 0.11503(10) 0.04214(7) 0.73508(7) 0.01279(11) Uani d . 1 . . N C15 -0.01414(12) 0.01352(9) 0.80825(9) 0.01652(13) Uani d . 1 . . C C16 0.03543(12) -0.20924(9) 0.59301(9) 0.01596(13) Uani d . 1 . . C C17 -0.09833(12) -0.24197(9) 0.66631(10) 0.01797(14) Uani d . 1 . . C C18 0.29916(12) -0.02137(10) 0.56108(9) 0.01633(13) Uani d . 1 . . C C7 -0.12307(13) -0.12976(10) 0.77685(10) 0.01874(14) Uani d . 1 . . C H151 -0.022(2) 0.0983(17) 0.8802(16) 0.025(3) Uiso d . 1 . . H H161 0.054(2) -0.2850(18) 0.5181(17) 0.028(4) Uiso d . 1 . . H H171 -0.175(2) -0.3386(16) 0.6387(16) 0.022(3) Uiso d . 1 . . H H71 -0.217(2) -0.1508(19) 0.8287(18) 0.032(4) Uiso d . 1 . . H H5 0.267(2) -0.0777(17) 0.4575(17) 0.027(4) Uiso d . 1 . . H H6 0.418(3) -0.046(2) 0.6156(19) 0.041(4) Uiso d . 1 . . H H7 0.424(3) 0.928(2) 1.084(2) 0.047(5) Uiso d . 1 . . H H8 0.325(2) 0.0859(19) 0.5704(17) 0.030(4) Uiso d . 1 . . H H1 0.173(2) 0.1387(19) 0.7549(17) 0.031(4) Uiso d . 1 . . H 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 0.0151(3) 0.0109(3) 0.0110(3) 0.0019(2) 0.0035(2) 0.0035(2) C2 0.0120(3) 0.0104(3) 0.0132(3) 0.0009(2) 0.0010(2) 0.0033(2) C3 0.0114(3) 0.0091(3) 0.0139(3) 0.0013(2) 0.0024(2) 0.0020(2) C4 0.0138(3) 0.0089(3) 0.0118(3) 0.0018(2) 0.0041(2) 0.0020(2) C5 0.0126(3) 0.0087(3) 0.0119(3) 0.0023(2) 0.0029(2) 0.0026(2) C6 0.0142(3) 0.0091(3) 0.0109(3) 0.0019(2) 0.0024(2) 0.0021(2) O7 0.0256(3) 0.0089(2) 0.0130(2) 0.0010(2) 0.0068(2) 0.00092(18) O8 0.0215(3) 0.0084(2) 0.0152(2) 0.00009(19) 0.0060(2) 0.00273(18) Cl9 0.01852(9) 0.01255(8) 0.01354(8) 0.00273(6) 0.00729(6) 0.00154(6) O10 0.0204(3) 0.0087(2) 0.0175(3) 0.00007(19) 0.0061(2) -0.00013(18) O11 0.0226(3) 0.0112(2) 0.0179(3) -0.0019(2) 0.0021(2) 0.0057(2) Cl12 0.02350(10) 0.01703(9) 0.01288(8) 0.00285(7) 0.00644(6) 0.00596(6) C13 0.0129(3) 0.0116(3) 0.0121(3) 0.0027(2) 0.0017(2) 0.0030(2) N14 0.0144(3) 0.0095(2) 0.0135(3) 0.0000(2) 0.0038(2) 0.0022(2) C15 0.0184(3) 0.0145(3) 0.0160(3) -0.0008(2) 0.0070(3) 0.0019(2) C16 0.0159(3) 0.0112(3) 0.0178(3) 0.0021(2) 0.0015(3) 0.0009(2) C17 0.0173(3) 0.0113(3) 0.0227(4) -0.0010(2) 0.0025(3) 0.0041(3) C18 0.0167(3) 0.0181(3) 0.0152(3) 0.0035(3) 0.0059(3) 0.0042(3) C7 0.0194(3) 0.0164(3) 0.0202(3) -0.0022(3) 0.0072(3) 0.0053(3) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 C6 . 1.3540(11) ? C1 C2 . 1.4552(12) ? C1 Cl12 . 1.7217(8) ? C2 O11 . 1.2217(10) ? C2 C3 . 1.5493(11) ? C3 O10 . 1.2497(10) ? C3 C4 . 1.4028(11) ? C4 C5 . 1.4058(11) ? C4 Cl9 . 1.7293(8) ? C5 O8 . 1.2492(9) ? C5 C6 . 1.5091(11) ? C6 O7 . 1.3257(10) ? O7 H7 . 0.85(2) ? C13 N14 . 1.3489(11) ? C13 C16 . 1.3930(12) ? C13 C18 . 1.4924(12) ? N14 C15 . 1.3490(11) ? N14 H1 . 0.892(16) ? C15 C7 . 1.3797(13) ? C15 H151 . 0.952(15) ? C16 C17 . 1.3855(13) ? C16 H161 . 0.949(15) ? C17 C7 . 1.3933(13) ? C17 H171 . 0.936(14) ? C18 H5 . 0.991(15) ? C18 H6 . 0.984(18) ? C18 H8 . 0.957(16) ? C7 H71 . 0.969(16) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.06(7) . . ? C6 C1 Cl12 121.02(6) . . ? C2 C1 Cl12 118.88(6) . . ? O11 C2 C1 123.21(7) . . ? O11 C2 C3 118.23(7) . . ? C1 C2 C3 118.55(7) . . ? O10 C3 C4 125.12(7) . . ? O10 C3 C2 116.85(7) . . ? C4 C3 C2 118.02(7) . . ? C3 C4 C5 122.49(7) . . ? C3 C4 Cl9 119.16(6) . . ? C5 C4 Cl9 118.28(6) . . ? O8 C5 C4 125.84(7) . . ? O8 C5 C6 115.78(7) . . ? C4 C5 C6 118.38(7) . . ? O7 C6 C1 121.86(7) . . ? O7 C6 C5 115.75(7) . . ? C1 C6 C5 122.39(7) . . ? C6 O7 H7 106.5(13) . . ? N14 C13 C16 117.93(7) . . ? N14 C13 C18 118.41(7) . . ? C16 C13 C18 123.66(7) . . ? C13 N14 C15 123.13(7) . . ? C13 N14 H1 120.7(10) . . ? C15 N14 H1 116.0(10) . . ? N14 C15 C7 120.38(8) . . ? N14 C15 H151 114.8(9) . . ? C7 C15 H151 124.8(9) . . ? C17 C16 C13 120.20(8) . . ? C17 C16 H161 120.8(9) . . ? C13 C16 H161 119.0(9) . . ? C16 C17 C7 120.09(8) . . ? C16 C17 H171 119.7(9) . . ? C7 C17 H171 120.2(9) . . ? C13 C18 H5 111.4(9) . . ? C13 C18 H6 108.1(10) . . ? H5 C18 H6 109.3(13) . . ? C13 C18 H8 111.2(9) . . ? H5 C18 H8 111.0(13) . . ? H6 C18 H8 105.6(14) . . ? C15 C7 C17 118.23(8) . . ? C15 C7 H71 120.7(10) . . ? C17 C7 H71 121.0(10) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O11 175.76(8) . . . . ? Cl12 C1 C2 O11 -1.87(11) . . . . ? C6 C1 C2 C3 -3.09(11) . . . . ? Cl12 C1 C2 C3 179.29(5) . . . . ? O11 C2 C3 O10 1.25(11) . . . . ? C1 C2 C3 O10 -179.84(7) . . . . ? O11 C2 C3 C4 -178.10(7) . . . . ? C1 C2 C3 C4 0.80(10) . . . . ? O10 C3 C4 C5 -177.04(7) . . . . ? C2 C3 C4 C5 2.26(11) . . . . ? O10 C3 C4 Cl9 -0.13(11) . . . . ? C2 C3 C4 Cl9 179.17(5) . . . . ? C3 C4 C5 O8 177.23(7) . . . . ? Cl9 C4 C5 O8 0.29(11) . . . . ? C3 C4 C5 C6 -3.01(11) . . . . ? Cl9 C4 C5 C6 -179.95(5) . . . . ? C2 C1 C6 O7 -177.50(7) . . . . ? Cl12 C1 C6 O7 0.08(11) . . . . ? C2 C1 C6 C5 2.43(11) . . . . ? Cl12 C1 C6 C5 180.00(5) . . . . ? O8 C5 C6 O7 0.32(10) . . . . ? C4 C5 C6 O7 -179.47(7) . . . . ? O8 C5 C6 C1 -179.61(7) . . . . ? C4 C5 C6 C1 0.60(11) . . . . ? C16 C13 N14 C15 1.88(11) . . . . ? C18 C13 N14 C15 -177.23(7) . . . . ? C13 N14 C15 C7 -0.35(13) . . . . ? N14 C13 C16 C17 -1.83(11) . . . . ? C18 C13 C16 C17 177.24(8) . . . . ? C13 C16 C17 C7 0.29(12) . . . . ? N14 C15 C7 C17 -1.24(13) . . . . ? C16 C17 C7 C15 1.24(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N14 H1 O10 0.892(16) 1.831(16) 2.6848(11) 159.6(15) . N14 H1 O11 0.892(16) 2.550(16) 3.1269(15) 123.1(12) . _chemical_name_common '2-picoline chloranilate' # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment '2Pic_2to1.cif' data_2pic_2to1_100 _database_code_depnum_ccdc_archive 'CCDC 744785' _oxford_structure_analysis_title '2pic100k in P 1 21/c 1' _chemical_name_systematic 'bis(2-picoline) chloranilate' _chemical_melting_point ? _cell_length_a 6.369(3) _cell_length_b 8.597(3) _cell_length_c 16.628(6) _cell_angle_alpha 90 _cell_angle_beta 101.451(17) _cell_angle_gamma 90 _cell_volume 892.3(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_formula_units_Z 2 # Given Formula = C10 H10 Cl1 N1 O2 # Dc = 1.58 Fooo = 408.00 Mu = 3.96 M = 211.65 # Found Formula = C9 H8 Cl1 N1 O2 # Dc = 1.47 FOOO = 408.00 Mu = 3.90 M = 197.62 _chemical_formula_sum 'C18 H16 Cl2 N2 O4' _chemical_formula_moiety '2(C6 H8 N), (C6 Cl2 O4)' _chemical_compound_source ? _chemical_formula_weight 395.24 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 100 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.390 # Sheldrick geometric approximatio 0.89 0.92 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8895 _exptl_absorpt_correction_T_max 0.9249 _exptl_absorpt_process_details 'CrystalClear 1.4.0 (Rigaku, 2008)' _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 11112 _reflns_number_total 2710 _diffrn_reflns_av_R_equivalents 0.0329 # Number of reflections with Friedels Law is 2710 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2724 _diffrn_reflns_theta_min 3.264 _diffrn_reflns_theta_max 30.505 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.505 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -9 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.443 _refine_diff_density_max 0.451 _refine_ls_number_reflns 2710 _refine_ls_number_restraints 0 _refine_ls_number_parameters 150 #_refine_ls_R_factor_ref 0.0556 _refine_ls_wR_factor_ref 0.1113 _refine_ls_goodness_of_fit_ref 1.05 #_reflns_number_all 2710 _refine_ls_R_factor_all 0.0557 _refine_ls_wR_factor_all 0.0955 _reflns_threshold_expression >2\s(I) _reflns_number_gt 1971 _refine_ls_R_factor_gt 0.0441 _refine_ls_shift/su_max 0 _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+0.5353P] where P=(Fo^2^+2Fc^2^)/3' 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C3 0.3299(2) 0.38918(17) 0.47924(8) 0.0221(3) Uani d . 1 . . C C2 0.4323(2) 0.44237(17) 0.41630(9) 0.0220(3) Uani d . 1 . . C C1 0.6176(2) 0.56053(17) 0.43958(9) 0.0221(3) Uani d . 1 . . C O1 0.70627(19) 0.60539(14) 0.38284(6) 0.0284(3) Uani d . 1 . . O O2 0.38568(19) 0.40165(15) 0.34357(6) 0.0300(3) Uani d . 1 . . O Cl1 0.12667(7) 0.25138(5) 0.45343(2) 0.03141(13) Uani d . 1 . . Cl C4 0.5664(3) 0.46872(18) 0.16694(9) 0.0261(3) Uani d . 1 . . C N1 0.7010(2) 0.46676(15) 0.23960(7) 0.0225(3) Uani d . 1 . . N C8 0.8915(3) 0.3958(2) 0.25299(13) 0.0369(4) Uani d . 1 . . C C7 0.9582(4) 0.3171(2) 0.19329(18) 0.0512(6) Uani d . 1 . . C C6 0.8271(5) 0.3102(2) 0.11802(18) 0.0613(8) Uani d . 1 . . C C5 0.6311(4) 0.3861(2) 0.10334(11) 0.0478(6) Uani d . 1 . . C C9 0.3653(3) 0.5574(3) 0.15856(18) 0.0504(6) Uani d . 1 . . C H8 0.974(4) 0.404(3) 0.3095(16) 0.057(7) Uiso d . 1 . . H H7 1.102(5) 0.264(3) 0.2027(17) 0.068(9) Uiso d . 1 . . H H6 0.869(5) 0.262(4) 0.084(2) 0.081(10) Uiso d . 1 . . H H5 0.534(5) 0.389(3) 0.0569(19) 0.072(9) Uiso d . 1 . . H H1 0.666(4) 0.511(3) 0.2836(16) 0.055(7) Uiso d . 1 . . H H92 0.390(5) 0.665(4) 0.1507(18) 0.075(9) Uiso d . 1 . . H H93 0.319(4) 0.557(3) 0.2109(17) 0.058(7) Uiso d . 1 . . H H91 0.252(5) 0.512(4) 0.1113(19) 0.082(10) Uiso d . 1 . . H 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 C3 0.0227(7) 0.0249(7) 0.0198(6) -0.0047(5) 0.0069(5) -0.0015(5) C2 0.0213(7) 0.0259(7) 0.0203(6) -0.0005(5) 0.0080(5) -0.0005(5) C1 0.0229(7) 0.0256(7) 0.0195(6) -0.0007(5) 0.0082(5) -0.0004(5) O1 0.0311(6) 0.0374(6) 0.0195(5) -0.0092(5) 0.0121(4) -0.0029(4) O2 0.0295(6) 0.0434(7) 0.0184(5) -0.0079(5) 0.0083(4) -0.0057(5) Cl1 0.0336(2) 0.0382(2) 0.02381(19) -0.01513(16) 0.00900(15) -0.00385(15) C4 0.0275(7) 0.0264(7) 0.0236(7) -0.0079(6) 0.0029(6) 0.0054(6) N1 0.0224(6) 0.0280(6) 0.0187(5) -0.0024(5) 0.0082(5) -0.0010(5) C8 0.0225(8) 0.0388(9) 0.0501(11) 0.0004(7) 0.0088(7) 0.0137(8) C7 0.0464(12) 0.0307(9) 0.0894(18) 0.0026(8) 0.0449(12) 0.0044(10) C6 0.097(2) 0.0284(9) 0.0827(18) -0.0170(11) 0.0758(18) -0.0202(10) C5 0.0809(16) 0.0426(10) 0.0207(8) -0.0331(11) 0.0123(9) -0.0057(7) C9 0.0287(10) 0.0485(12) 0.0716(16) 0.0026(9) 0.0045(10) 0.0289(11) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C3 C1 3_666 1.393(2) ? C3 C2 . 1.4147(19) ? C3 Cl1 . 1.7441(16) ? C2 O2 . 1.2372(18) ? C2 C1 . 1.547(2) ? C1 O1 . 1.2529(17) ? C1 C3 3_666 1.393(2) ? C4 N1 . 1.336(2) ? C4 C5 . 1.402(3) ? C4 C9 . 1.473(3) ? N1 C8 . 1.336(2) ? N1 H1 . 0.89(3) ? C8 C7 . 1.338(3) ? C8 H8 . 0.98(3) ? C7 C6 . 1.361(4) ? C7 H7 . 1.01(3) ? C6 C5 . 1.387(4) ? C6 H6 . 0.79(4) ? C5 H5 . 0.89(3) ? C9 H92 . 0.95(3) ? C9 H93 . 0.97(3) ? C9 H91 . 1.03(3) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C3 C2 123.98(14) 3_666 . ? C1 C3 Cl1 118.23(11) 3_666 . ? C2 C3 Cl1 117.79(11) . . ? O2 C2 C3 125.12(14) . . ? O2 C2 C1 116.97(12) . . ? C3 C2 C1 117.91(12) . . ? O1 C1 C3 125.20(14) . 3_666 ? O1 C1 C2 116.70(13) . . ? C3 C1 C2 118.09(12) 3_666 . ? N1 C4 C5 116.34(18) . . ? N1 C4 C9 118.83(18) . . ? C5 C4 C9 124.8(2) . . ? C4 N1 C8 123.71(15) . . ? C4 N1 H1 121.1(16) . . ? C8 N1 H1 115.1(16) . . ? N1 C8 C7 121.2(2) . . ? N1 C8 H8 115.1(16) . . ? C7 C8 H8 123.7(16) . . ? C8 C7 C6 118.5(2) . . ? C8 C7 H7 121.8(16) . . ? C6 C7 H7 119.8(16) . . ? C7 C6 C5 120.51(18) . . ? C7 C6 H6 117(3) . . ? C5 C6 H6 123(3) . . ? C6 C5 C4 119.7(2) . . ? C6 C5 H5 128(2) . . ? C4 C5 H5 113(2) . . ? C4 C9 H92 110.6(19) . . ? C4 C9 H93 108.9(16) . . ? H92 C9 H93 102(2) . . ? C4 C9 H91 109.6(18) . . ? H92 C9 H91 112(2) . . ? H93 C9 H91 113(2) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C3 C2 O2 -178.55(15) 3_666 . . . ? Cl1 C3 C2 O2 1.9(2) . . . . ? C1 C3 C2 C1 1.6(3) 3_666 . . . ? Cl1 C3 C2 C1 -178.03(10) . . . . ? O2 C2 C1 O1 -0.2(2) . . . . ? C3 C2 C1 O1 179.72(14) . . . . ? O2 C2 C1 C3 178.64(14) . . . 3_666 ? C3 C2 C1 C3 -1.5(2) . . . 3_666 ? C5 C4 N1 C8 2.1(2) . . . . ? C9 C4 N1 C8 -176.99(16) . . . . ? C4 N1 C8 C7 -1.7(3) . . . . ? N1 C8 C7 C6 -0.2(3) . . . . ? C8 C7 C6 C5 1.5(3) . . . . ? C7 C6 C5 C4 -1.0(3) . . . . ? N1 C4 C5 C6 -0.8(2) . . . . ? C9 C4 C5 C6 178.28(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.89(3) 1.81(3) 2.6576(18) 158(2) . N1 H1 O2 0.89(3) 2.40(3) 2.9522(19) 120(2) . _chemical_name_common 'bis(2-picoline) chloranilate' data_2pic_2to1_200K _database_code_depnum_ccdc_archive 'CCDC 744786' _oxford_structure_analysis_title '2pic200k in P 21/n' _chemical_name_systematic 'bis(2-picoline) chloranilate' _chemical_melting_point ? _cell_length_a 6.398(3) _cell_length_b 8.657(4) _cell_length_c 16.684(7) _cell_angle_alpha 90 _cell_angle_beta 101.23(2) _cell_angle_gamma 90 _cell_volume 906.4(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C8 H8 Cl1 N1 O2 # Dc = 1.36 Fooo = 408.00 Mu = 3.79 M = 185.61 # Found Formula = C9 H8 Cl1 N1 O2 # Dc = 1.45 FOOO = 408.00 Mu = 3.84 M = 197.62 _chemical_formula_sum 'C18 H16 Cl2 N2 O4' _chemical_formula_moiety '2(C6 H8 N), (C6 Cl2 O4)' _chemical_compound_source ? _chemical_formula_weight 395.24 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 200 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.384 # Sheldrick geometric approximatio 0.89 0.93 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8911 _exptl_absorpt_correction_T_max 0.9260 _exptl_absorpt_process_details 'CrystalClear 1.4.0 (Rigaku, 2008)' _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 11669 _reflns_number_total 2755 _diffrn_reflns_av_R_equivalents 0.0278 # Number of reflections with Friedels Law is 2755 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2766 _diffrn_reflns_theta_min 3.246 _diffrn_reflns_theta_max 30.502 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.502 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -9 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.314 _refine_diff_density_max 0.308 _refine_ls_number_reflns 2755 _refine_ls_number_restraints 0 _refine_ls_number_parameters 150 #_refine_ls_R_factor_ref 0.0646 _refine_ls_wR_factor_ref 0.1007 _refine_ls_goodness_of_fit_ref 1.055 #_reflns_number_all 2755 _refine_ls_R_factor_all 0.0646 _refine_ls_wR_factor_all 0.1218 _reflns_threshold_expression >2\s(I) _reflns_number_gt 2038 _refine_ls_R_factor_gt 0.046 _refine_ls_shift/su_max 0.001 _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+0.2496P] where P=(Fo^2^+2Fc^2^)/3' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C3 0.3319(2) 0.38911(18) 0.47988(9) 0.0360(3) Uani d . 1 . . C C2 0.4338(2) 0.44135(18) 0.41705(8) 0.0353(3) Uani d . 1 . . C C1 0.6162(2) 0.55987(18) 0.43956(8) 0.0355(3) Uani d . 1 . . C O1 0.7048(2) 0.60416(15) 0.38265(6) 0.0465(3) Uani d . 1 . . O O2 0.3880(2) 0.40000(16) 0.34472(7) 0.0489(3) Uani d . 1 . . O Cl1 0.13080(7) 0.25120(5) 0.45477(2) 0.05143(16) Uani d . 1 . . Cl C4 0.5702(3) 0.46636(19) 0.16780(10) 0.0412(4) Uani d . 1 . . C N1 0.7021(2) 0.46368(16) 0.24023(8) 0.0382(3) Uani d . 1 . . N C8 0.8904(3) 0.3924(2) 0.25397(14) 0.0568(5) Uani d . 1 . . C C7 0.9578(4) 0.3153(3) 0.1952(2) 0.0757(7) Uani d . 1 . . C C6 0.8329(6) 0.3089(3) 0.1207(2) 0.0875(11) Uani d . 1 . . C C5 0.6380(5) 0.3845(3) 0.10488(12) 0.0692(7) Uani d . 1 . . C C9 0.3704(4) 0.5550(4) 0.1594(2) 0.0784(8) Uani d . 1 . . C H8 0.973(4) 0.398(3) 0.3083(16) 0.079(8) Uiso d . 1 . . H H7 1.097(5) 0.260(3) 0.2065(18) 0.095(10) Uiso d . 1 . . H H6 0.869(6) 0.258(4) 0.086(3) 0.114(12) Uiso d . 1 . . H H5 0.550(5) 0.385(3) 0.0623(18) 0.084(8) Uiso d . 1 . . H H1 0.670(4) 0.508(3) 0.2827(15) 0.068(7) Uiso d . 1 . . H H92 0.390(6) 0.657(5) 0.150(2) 0.128(12) Uiso d . 1 . . H H93 0.316(5) 0.551(4) 0.209(2) 0.101(10) Uiso d . 1 . . H H91 0.264(6) 0.505(5) 0.119(2) 0.137(14) Uiso d . 1 . . H 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 C3 0.0373(8) 0.0409(8) 0.0317(7) -0.0048(6) 0.0112(6) -0.0016(6) C2 0.0362(8) 0.0426(8) 0.0290(6) 0.0001(6) 0.0113(6) -0.0015(6) C1 0.0382(8) 0.0409(8) 0.0304(6) -0.0001(6) 0.0140(6) -0.0003(6) O1 0.0522(7) 0.0604(7) 0.0321(5) -0.0142(6) 0.0209(5) -0.0049(5) O2 0.0501(7) 0.0699(8) 0.0292(5) -0.0138(6) 0.0136(5) -0.0099(5) Cl1 0.0556(3) 0.0619(3) 0.0385(2) -0.0232(2) 0.01334(18) -0.00546(18) C4 0.0424(8) 0.0439(8) 0.0374(7) -0.0122(7) 0.0079(6) 0.0062(6) N1 0.0408(7) 0.0479(8) 0.0288(6) -0.0034(6) 0.0137(5) -0.0027(5) C8 0.0386(9) 0.0627(12) 0.0690(13) -0.0002(8) 0.0103(9) 0.0153(10) C7 0.0667(15) 0.0526(12) 0.123(2) 0.0019(11) 0.0568(16) -0.0009(14) C6 0.126(3) 0.0510(12) 0.115(2) -0.0229(14) 0.096(2) -0.0313(14) C5 0.109(2) 0.0671(13) 0.0321(8) -0.0422(14) 0.0153(11) -0.0100(9) C9 0.0468(12) 0.0768(17) 0.109(2) 0.0030(11) 0.0097(13) 0.0397(16) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C3 C1 3_666 1.392(2) ? C3 C2 . 1.412(2) ? C3 Cl1 . 1.7455(17) ? C2 O2 . 1.2380(18) ? C2 C1 . 1.545(2) ? C1 O1 . 1.2565(17) ? C1 C3 3_666 1.392(2) ? C4 N1 . 1.333(2) ? C4 C5 . 1.403(3) ? C4 C9 . 1.474(3) ? N1 C8 . 1.333(2) ? N1 H1 . 0.87(3) ? C8 C7 . 1.327(3) ? C8 H8 . 0.96(3) ? C7 C6 . 1.341(4) ? C7 H7 . 0.99(3) ? C6 C5 . 1.388(5) ? C6 H6 . 0.80(4) ? C5 H5 . 0.82(3) ? C9 H92 . 0.91(4) ? C9 H93 . 0.96(3) ? C9 H91 . 0.96(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C3 C2 123.89(14) 3_666 . ? C1 C3 Cl1 118.33(11) 3_666 . ? C2 C3 Cl1 117.78(11) . . ? O2 C2 C3 125.13(15) . . ? O2 C2 C1 116.94(12) . . ? C3 C2 C1 117.93(12) . . ? O1 C1 C3 125.11(15) . 3_666 ? O1 C1 C2 116.72(13) . . ? C3 C1 C2 118.17(12) 3_666 . ? N1 C4 C5 115.86(19) . . ? N1 C4 C9 118.7(2) . . ? C5 C4 C9 125.4(2) . . ? C4 N1 C8 123.75(17) . . ? C4 N1 H1 121.7(16) . . ? C8 N1 H1 114.6(16) . . ? C7 C8 N1 121.3(2) . . ? C7 C8 H8 121.9(16) . . ? N1 C8 H8 116.9(16) . . ? C8 C7 C6 119.0(2) . . ? C8 C7 H7 120.6(18) . . ? C6 C7 H7 120.4(17) . . ? C7 C6 C5 120.6(2) . . ? C7 C6 H6 120(3) . . ? C5 C6 H6 120(3) . . ? C6 C5 C4 119.5(2) . . ? C6 C5 H5 128(2) . . ? C4 C5 H5 113(2) . . ? C4 C9 H92 112(2) . . ? C4 C9 H93 110.5(19) . . ? H92 C9 H93 106(3) . . ? C4 C9 H91 108(2) . . ? H92 C9 H91 115(3) . . ? H93 C9 H91 105(3) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C3 C2 O2 -178.57(16) 3_666 . . . ? Cl1 C3 C2 O2 2.0(2) . . . . ? C1 C3 C2 C1 1.2(3) 3_666 . . . ? Cl1 C3 C2 C1 -178.27(11) . . . . ? O2 C2 C1 O1 -0.5(2) . . . . ? C3 C2 C1 O1 179.77(14) . . . . ? O2 C2 C1 C3 178.66(15) . . . 3_666 ? C3 C2 C1 C3 -1.1(2) . . . 3_666 ? C5 C4 N1 C8 1.7(2) . . . . ? C9 C4 N1 C8 -177.29(19) . . . . ? C4 N1 C8 C7 -1.4(3) . . . . ? N1 C8 C7 C6 -0.2(3) . . . . ? C8 C7 C6 C5 1.3(4) . . . . ? C7 C6 C5 C4 -1.0(3) . . . . ? N1 C4 C5 C6 -0.5(3) . . . . ? C9 C4 C5 C6 178.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.87(3) 1.84(3) 2.6664(19) 160(2) . N1 H1 O2 0.87(3) 2.44(2) 2.9572(19) 119.2(19) . _chemical_name_common 'bis(2-picoline) chloranilate' data_2pic_2to1_300K _database_code_depnum_ccdc_archive 'CCDC 744787' _oxford_structure_analysis_title '2picRT in P 1 21/c 1' _chemical_name_systematic 'bis(2-picoline) chloranilate' _chemical_melting_point ? _cell_length_a 6.419(3) _cell_length_b 8.692(4) _cell_length_c 16.727(7) _cell_angle_alpha 90 _cell_angle_beta 101.031(19) _cell_angle_gamma 90 _cell_volume 916.1(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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' Cl Cl 0.1484 0.1585 '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' _cell_formula_units_Z 2 # Given Formula = C10 H10 Cl1 N1 O2 # Dc = 1.53 Fooo = 408.00 Mu = 3.86 M = 211.65 # Found Formula = C9 H8 Cl1 N1 O2 # Dc = 1.43 FOOO = 408.00 Mu = 3.80 M = 197.62 _chemical_formula_sum 'C18 H16 Cl2 N2 O4' _chemical_formula_moiety '2(C6 H8 N), (C6 Cl2 O4)' _chemical_compound_source ? _chemical_formula_weight 395.24 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 300 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.380 # Sheldrick geometric approximatio 0.89 0.93 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8922 _exptl_absorpt_correction_T_max 0.9268 _exptl_absorpt_process_details 'CrystalClear 1.4.0 (Rigaku, 2008)' _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 300 _diffrn_reflns_number 11403 _reflns_number_total 2781 _diffrn_reflns_av_R_equivalents 0.0248 # Number of reflections with Friedels Law is 2781 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2792 _diffrn_reflns_theta_min 3.233 _diffrn_reflns_theta_max 30.488 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.488 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -9 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.256 _refine_diff_density_max 0.22 _refine_ls_number_reflns 2781 _refine_ls_number_restraints 0 _refine_ls_number_parameters 150 #_refine_ls_R_factor_ref 0.0742 _refine_ls_wR_factor_ref 0.1379 _refine_ls_goodness_of_fit_ref 1.046 #_reflns_number_all 2781 _refine_ls_R_factor_all 0.0755 _refine_ls_wR_factor_all 0.1046 _reflns_threshold_expression >2\s(I) _reflns_number_gt 1747 _refine_ls_R_factor_gt 0.0462 _refine_ls_shift/su_max 0 _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+0.1143P] where P=(Fo^2^+2Fc^2^)/3' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C3 0.3341(3) 0.38867(19) 0.48057(9) 0.0529(4) Uani d . 1 . . C C2 0.4357(3) 0.44028(19) 0.41797(9) 0.0528(4) Uani d . 1 . . C C1 0.6151(3) 0.5590(2) 0.43967(9) 0.0526(4) Uani d . 1 . . C O1 0.7032(2) 0.60242(16) 0.38270(7) 0.0689(4) Uani d . 1 . . O O2 0.3913(2) 0.39713(17) 0.34638(7) 0.0728(4) Uani d . 1 . . O Cl1 0.13594(9) 0.25040(6) 0.45648(3) 0.0764(2) Uani d . 1 . . Cl C4 0.5755(3) 0.4622(2) 0.16902(10) 0.0589(4) Uani d . 1 . . C N1 0.7031(2) 0.45793(18) 0.24126(8) 0.0581(4) Uani d . 1 . . N C8 0.8892(4) 0.3869(3) 0.25567(16) 0.0818(6) Uani d . 1 . . C C7 0.9604(5) 0.3118(3) 0.1989(3) 0.1022(9) Uani d . 1 . . C C6 0.8424(7) 0.3059(3) 0.1248(3) 0.1147(14) Uani d . 1 . . C C5 0.6488(6) 0.3809(3) 0.10704(13) 0.0932(9) Uani d . 1 . . C C9 0.3769(5) 0.5495(4) 0.1596(3) 0.1069(10) Uani d . 1 . . C H8 0.969(4) 0.393(3) 0.3120(16) 0.106(8) Uiso d . 1 . . H H7 1.108(5) 0.258(3) 0.2084(18) 0.122(11) Uiso d . 1 . . H H6 0.893(5) 0.253(3) 0.095(2) 0.124(11) Uiso d . 1 . . H H5 0.555(5) 0.387(3) 0.0666(18) 0.104(9) Uiso d . 1 . . H H1 0.671(4) 0.500(3) 0.2789(16) 0.091(7) Uiso d . 1 . . H H92 0.395(7) 0.653(6) 0.146(3) 0.183(16) Uiso d . 1 . . H H93 0.330(5) 0.553(4) 0.213(2) 0.135(12) Uiso d . 1 . . H H91 0.275(7) 0.497(5) 0.121(3) 0.181(17) Uiso d . 1 . . H 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 C3 0.0561(9) 0.0621(9) 0.0433(7) -0.0050(7) 0.0168(6) -0.0016(6) C2 0.0564(9) 0.0638(9) 0.0419(7) 0.0012(7) 0.0184(6) -0.0026(6) C1 0.0575(9) 0.0624(9) 0.0424(7) 0.0013(7) 0.0207(6) -0.0007(6) O1 0.0785(8) 0.0882(9) 0.0477(6) -0.0193(7) 0.0316(5) -0.0069(6) O2 0.0770(8) 0.1034(10) 0.0418(6) -0.0209(7) 0.0209(5) -0.0143(6) Cl1 0.0833(4) 0.0917(4) 0.0568(3) -0.0315(3) 0.0203(2) -0.0069(2) C4 0.0619(10) 0.0637(10) 0.0527(8) -0.0147(8) 0.0153(7) 0.0061(7) N1 0.0645(9) 0.0709(9) 0.0439(7) -0.0035(7) 0.0230(6) -0.0042(6) C8 0.0612(12) 0.0907(15) 0.0938(16) -0.0004(11) 0.0161(11) 0.0151(12) C7 0.0896(18) 0.0791(15) 0.155(3) 0.0023(14) 0.0662(19) -0.0051(18) C6 0.151(3) 0.0774(15) 0.150(3) -0.0234(18) 0.114(3) -0.0389(18) C5 0.137(2) 0.0969(17) 0.0470(10) -0.0507(18) 0.0211(13) -0.0133(10) C9 0.0743(16) 0.107(2) 0.137(3) 0.0044(15) 0.0152(17) 0.045(2) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C3 C1 3_666 1.388(2) ? C3 C2 . 1.409(2) ? C3 Cl1 . 1.7403(18) ? C2 O2 . 1.2350(18) ? C2 C1 . 1.537(2) ? C1 O1 . 1.2556(17) ? C1 C3 3_666 1.388(2) ? C4 N1 . 1.324(2) ? C4 C5 . 1.408(3) ? C4 C9 . 1.466(4) ? N1 C8 . 1.325(3) ? N1 H1 . 0.79(3) ? C8 C7 . 1.305(4) ? C8 H8 . 0.98(3) ? C7 C6 . 1.323(5) ? C7 H7 . 1.04(3) ? C6 C5 . 1.384(5) ? C6 H6 . 0.79(4) ? C5 H5 . 0.82(3) ? C9 H92 . 0.94(5) ? C9 H93 . 1.00(4) ? C9 H91 . 0.94(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C3 C2 123.57(15) 3_666 . ? C1 C3 Cl1 118.41(12) 3_666 . ? C2 C3 Cl1 118.01(12) . . ? O2 C2 C3 124.75(16) . . ? O2 C2 C1 117.17(13) . . ? C3 C2 C1 118.08(13) . . ? O1 C1 C3 125.01(16) . 3_666 ? O1 C1 C2 116.64(13) . . ? C3 C1 C2 118.34(13) 3_666 . ? N1 C4 C5 115.0(2) . . ? N1 C4 C9 119.1(2) . . ? C5 C4 C9 126.0(3) . . ? C4 N1 C8 123.89(18) . . ? C4 N1 H1 120.5(18) . . ? C8 N1 H1 115.6(18) . . ? C7 C8 N1 122.0(3) . . ? C7 C8 H8 122.2(16) . . ? N1 C8 H8 115.8(16) . . ? C8 C7 C6 118.9(3) . . ? C8 C7 H7 123.2(17) . . ? C6 C7 H7 117.9(17) . . ? C7 C6 C5 120.9(2) . . ? C7 C6 H6 113(3) . . ? C5 C6 H6 126(3) . . ? C6 C5 C4 119.4(2) . . ? C6 C5 H5 134(2) . . ? C4 C5 H5 106(2) . . ? C4 C9 H92 112(3) . . ? C4 C9 H93 108.7(19) . . ? H92 C9 H93 106(3) . . ? C4 C9 H91 107(3) . . ? H92 C9 H91 113(4) . . ? H93 C9 H91 110(3) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C3 C2 O2 -178.88(17) 3_666 . . . ? Cl1 C3 C2 O2 1.7(3) . . . . ? C1 C3 C2 C1 1.1(3) 3_666 . . . ? Cl1 C3 C2 C1 -178.29(11) . . . . ? O2 C2 C1 O1 -0.3(2) . . . . ? C3 C2 C1 O1 179.77(15) . . . . ? O2 C2 C1 C3 178.94(16) . . . 3_666 ? C3 C2 C1 C3 -1.0(3) . . . 3_666 ? C5 C4 N1 C8 1.7(3) . . . . ? C9 C4 N1 C8 -177.6(2) . . . . ? C4 N1 C8 C7 -1.3(3) . . . . ? N1 C8 C7 C6 -0.4(4) . . . . ? C8 C7 C6 C5 1.6(4) . . . . ? C7 C6 C5 C4 -1.1(4) . . . . ? N1 C4 C5 C6 -0.5(3) . . . . ? C9 C4 C5 C6 178.8(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.79(3) 1.93(3) 2.678(2) 159(2) . N1 H1 O2 0.79(3) 2.47(3) 2.954(2) 121(2) . _chemical_name_common 'bis(2-picoline) chloranilate' # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment '3pic_1_1.cif' data_3pic_1_1_100K _database_code_depnum_ccdc_archive 'CCDC 744788' _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint _chemical_name_systematic '3-picoline chloranilate' _chemical_melting_point ? _cell_length_a 5.0366(2) _cell_length_b 9.3637(4) _cell_length_c 13.3491(7) _cell_angle_alpha 97.669(2) _cell_angle_beta 98.579(3) _cell_angle_gamma 103.660(2) _cell_volume 595.51(5) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C13 H6 Cl2 N1 O4 # Dc = 1.73 Fooo = 308.00 Mu = 5.57 M = 311.10 # Found Formula = C12 H9 Cl2 N1 O4 # Dc = 1.68 FOOO = 308.00 Mu = 5.54 M = 302.11 _chemical_formula_sum 'C24 H18 Cl4 N2 O8' _chemical_formula_moiety '(C6 Cl2 O4 H2), (C6 Cl2 O4), 2(C6 N1 H8)' _chemical_compound_source ? _chemical_formula_weight 604.22 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 100 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.685 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.554 # Sheldrick geometric approximatio 0.85 0.90 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8469 _exptl_absorpt_correction_T_max 0.8951 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q _computing_data_collection 'Nonius (1997-2001). COLLECT.' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 13826 _reflns_number_total 5151 _diffrn_reflns_av_R_equivalents 0.044 # Number of reflections with Friedels Law is 5151 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5257 _diffrn_reflns_theta_min 1.567 _diffrn_reflns_theta_max 35.032 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 31.529 _diffrn_measured_fraction_theta_full 0.982 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -8 _reflns_limit_h_max 7 _reflns_limit_k_min -15 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.415 _refine_diff_density_max 0.541 _refine_ls_number_reflns 5151 _refine_ls_number_restraints 0 _refine_ls_number_parameters 208 #_refine_ls_R_factor_ref 0.0615 _refine_ls_wR_factor_ref 0.09 _refine_ls_goodness_of_fit_ref 1.017 #_reflns_number_all 5151 _refine_ls_R_factor_all 0.0619 _refine_ls_wR_factor_all 0.0941 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression >2\s(I) _reflns_number_gt 3937 _refine_ls_R_factor_gt 0.0379 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+0.2420P] where P=(Fo^2^+2Fc^2^)/3' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 -0.1347(2) 0.40280(13) 0.40250(9) 0.0116(2) Uani d . 1 . . C C2 0.1330(2) 0.52361(13) 0.41252(9) 0.0120(2) Uani d . 1 . . C C3 0.2535(2) 0.61506(13) 0.51348(9) 0.0119(2) Uani d . 1 . . C Cl4 0.55894(6) 0.75173(3) 0.52294(2) 0.01642(7) Uani d . 1 . . Cl O5 0.23641(19) 0.53849(11) 0.33621(7) 0.01638(18) Uani d . 1 . . O O6 -0.24099(19) 0.31733(10) 0.31252(7) 0.01397(17) Uani d . 1 . . O C7 -0.0472(2) 0.40833(13) 0.07883(9) 0.0105(2) Uani d . 1 . . C C8 0.1184(2) 0.37275(13) -0.00531(9) 0.0103(2) Uani d . 1 . . C C9 -0.1536(2) 0.53149(13) 0.07914(9) 0.0110(2) Uani d . 1 . . C Cl10 -0.34886(6) 0.56837(3) 0.17161(2) 0.01272(7) Uani d . 1 . . Cl O11 0.21027(19) 0.26156(10) -0.00340(7) 0.01451(17) Uani d . 1 . . O O12 -0.07349(18) 0.31777(10) 0.14192(7) 0.01318(17) Uani d . 1 . . O C13 0.1336(3) -0.06504(14) 0.27928(10) 0.0131(2) Uani d . 1 . . C C14 0.0863(3) 0.05773(14) 0.23958(10) 0.0142(2) Uani d . 1 . . C N15 0.1975(2) 0.09995(12) 0.15968(9) 0.0149(2) Uani d . 1 . . N C16 0.3619(3) 0.02825(15) 0.11545(10) 0.0163(2) Uani d . 1 . . C C17 0.4148(3) -0.09700(14) 0.14997(10) 0.0153(2) Uani d . 1 . . C C18 0.2987(3) -0.14408(14) 0.23205(10) 0.0137(2) Uani d . 1 . . C C19 0.0083(3) -0.10955(16) 0.36937(11) 0.0181(2) Uani d . 1 . . C H141 -0.031(4) 0.116(2) 0.2651(14) 0.022(4) Uiso d . 1 . . H H161 0.437(4) 0.074(2) 0.0655(13) 0.019(4) Uiso d . 1 . . H H171 0.532(4) -0.145(2) 0.1188(14) 0.024(5) Uiso d . 1 . . H H181 0.333(4) -0.232(2) 0.2566(14) 0.023(4) Uiso d . 1 . . H H191 -0.095(4) -0.208(2) 0.3546(15) 0.032(5) Uiso d . 1 . . H H192 0.157(4) -0.097(2) 0.4291(15) 0.033(5) Uiso d . 1 . . H H193 -0.115(4) -0.045(2) 0.3857(16) 0.038(6) Uiso d . 1 . . H H8 0.155(4) 0.180(2) 0.1351(16) 0.039(6) Uiso d . 1 . . H H16 -0.154(5) 0.340(3) 0.255(2) 0.062(8) Uiso d . 1 . . H 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 0.0128(5) 0.0108(5) 0.0129(5) 0.0046(4) 0.0041(4) 0.0039(4) C2 0.0131(5) 0.0120(5) 0.0135(5) 0.0052(4) 0.0053(4) 0.0052(4) C3 0.0112(5) 0.0115(5) 0.0133(5) 0.0017(4) 0.0045(4) 0.0032(4) Cl4 0.01474(14) 0.01621(14) 0.01672(14) -0.00105(11) 0.00580(11) 0.00336(11) O5 0.0182(4) 0.0190(4) 0.0133(4) 0.0032(4) 0.0083(3) 0.0044(3) O6 0.0171(4) 0.0137(4) 0.0111(4) 0.0026(3) 0.0054(3) 0.0020(3) C7 0.0114(5) 0.0103(5) 0.0099(5) 0.0027(4) 0.0025(4) 0.0021(4) C8 0.0110(5) 0.0101(5) 0.0104(5) 0.0035(4) 0.0027(4) 0.0018(4) C9 0.0124(5) 0.0125(5) 0.0100(5) 0.0049(4) 0.0052(4) 0.0026(4) Cl10 0.01521(13) 0.01421(13) 0.01190(13) 0.00702(10) 0.00648(10) 0.00315(9) O11 0.0195(4) 0.0127(4) 0.0154(4) 0.0088(3) 0.0064(3) 0.0047(3) O12 0.0176(4) 0.0125(4) 0.0125(4) 0.0063(3) 0.0058(3) 0.0049(3) C13 0.0142(5) 0.0125(5) 0.0127(5) 0.0031(4) 0.0028(4) 0.0027(4) C14 0.0165(5) 0.0130(5) 0.0145(5) 0.0063(4) 0.0033(4) 0.0020(4) N15 0.0192(5) 0.0120(5) 0.0153(5) 0.0059(4) 0.0040(4) 0.0042(4) C16 0.0204(6) 0.0162(6) 0.0148(6) 0.0057(5) 0.0070(5) 0.0056(5) C17 0.0167(6) 0.0150(6) 0.0169(6) 0.0064(5) 0.0068(5) 0.0040(4) C18 0.0155(5) 0.0117(5) 0.0149(5) 0.0048(4) 0.0032(4) 0.0030(4) C19 0.0229(7) 0.0180(6) 0.0156(6) 0.0059(5) 0.0084(5) 0.0044(5) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 O6 . 1.3111(15) ? C1 C3 2_566 1.3589(16) ? C1 C2 . 1.5169(17) ? C2 O5 . 1.2206(14) ? C2 C3 . 1.4562(18) ? C3 C1 2_566 1.3589(16) ? C3 Cl4 . 1.7291(12) ? O6 H16 . 0.97(3) ? C7 O12 . 1.2715(14) ? C7 C9 . 1.3815(16) ? C7 C8 . 1.5423(16) ? C8 O11 . 1.2369(14) ? C8 C9 2_565 1.4212(16) ? C9 C8 2_565 1.4212(16) ? C9 Cl10 . 1.7375(11) ? C13 C14 . 1.3832(17) ? C13 C18 . 1.3997(17) ? C13 C19 . 1.5015(18) ? C14 N15 . 1.3396(17) ? C14 H141 . 0.962(18) ? N15 C16 . 1.3369(17) ? N15 H8 . 0.92(2) ? C16 C17 . 1.3834(18) ? C16 H161 . 0.922(18) ? C17 C18 . 1.3911(18) ? C17 H171 . 0.932(19) ? C18 H181 . 0.972(18) ? C19 H191 . 0.93(2) ? C19 H192 . 0.98(2) ? C19 H193 . 0.99(2) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 C1 C3 122.29(11) . 2_566 ? O6 C1 C2 118.27(10) . . ? C3 C1 C2 119.43(11) 2_566 . ? O5 C2 C3 123.61(11) . . ? O5 C2 C1 118.59(11) . . ? C3 C2 C1 117.80(10) . . ? C1 C3 C2 122.77(11) 2_566 . ? C1 C3 Cl4 120.32(10) 2_566 . ? C2 C3 Cl4 116.91(9) . . ? C1 O6 H16 118.4(16) . . ? O12 C7 C9 126.16(11) . . ? O12 C7 C8 115.16(10) . . ? C9 C7 C8 118.68(10) . . ? O11 C8 C9 124.81(11) . 2_565 ? O11 C8 C7 116.97(10) . . ? C9 C8 C7 118.22(10) 2_565 . ? C7 C9 C8 123.10(10) . 2_565 ? C7 C9 Cl10 118.66(9) . . ? C8 C9 Cl10 118.21(9) 2_565 . ? C14 C13 C18 117.52(11) . . ? C14 C13 C19 120.02(11) . . ? C18 C13 C19 122.45(11) . . ? N15 C14 C13 121.00(11) . . ? N15 C14 H141 115.7(11) . . ? C13 C14 H141 123.3(11) . . ? C16 N15 C14 122.29(11) . . ? C16 N15 H8 120.2(14) . . ? C14 N15 H8 117.5(14) . . ? N15 C16 C17 119.92(12) . . ? N15 C16 H161 113.1(11) . . ? C17 C16 H161 126.9(11) . . ? C16 C17 C18 118.81(11) . . ? C16 C17 H171 118.7(12) . . ? C18 C17 H171 122.4(11) . . ? C17 C18 C13 120.43(11) . . ? C17 C18 H181 119.6(11) . . ? C13 C18 H181 120.0(11) . . ? C13 C19 H191 111.1(12) . . ? C13 C19 H192 109.5(12) . . ? H191 C19 H192 108.6(17) . . ? C13 C19 H193 108.8(12) . . ? H191 C19 H193 108.8(17) . . ? H192 C19 H193 110.0(17) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O6 C1 C2 O5 1.32(16) . . . . ? C3 C1 C2 O5 -179.74(11) 2_566 . . . ? O6 C1 C2 C3 -178.27(10) . . . . ? C3 C1 C2 C3 0.67(18) 2_566 . . . ? O5 C2 C3 C1 179.73(12) . . . 2_566 ? C1 C2 C3 C1 -0.69(19) . . . 2_566 ? O5 C2 C3 Cl4 0.30(16) . . . . ? C1 C2 C3 Cl4 179.87(8) . . . . ? O12 C7 C8 O11 -0.36(16) . . . . ? C9 C7 C8 O11 -179.88(11) . . . . ? O12 C7 C8 C9 179.39(11) . . . 2_565 ? C9 C7 C8 C9 -0.14(18) . . . 2_565 ? O12 C7 C9 C8 -179.32(12) . . . 2_565 ? C8 C7 C9 C8 0.15(19) . . . 2_565 ? O12 C7 C9 Cl10 -1.34(18) . . . . ? C8 C7 C9 Cl10 178.12(8) . . . . ? C18 C13 C14 N15 -0.78(19) . . . . ? C19 C13 C14 N15 179.56(12) . . . . ? C13 C14 N15 C16 -1.1(2) . . . . ? C14 N15 C16 C17 2.1(2) . . . . ? N15 C16 C17 C18 -1.2(2) . . . . ? C16 C17 C18 C13 -0.6(2) . . . . ? C14 C13 C18 C17 1.57(19) . . . . ? C19 C13 C18 C17 -178.78(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N15 H8 O12 0.92(2) 1.92(2) 2.7253(14) 145.2(19) . N15 H8 O11 0.92(2) 2.12(2) 2.8122(14) 131.2(18) . O6 H16 O12 0.97(3) 1.62(3) 2.5441(12) 160(2) . _chemical_name_common '3-picoline chloranilate' data_3pic_1_1_200K _database_code_depnum_ccdc_archive 'CCDC 744789' _chemical_name_systematic '3-picoline chloranilate' _chemical_melting_point ? _cell_length_a 5.0539(2) _cell_length_b 9.3895(5) _cell_length_c 13.4239(8) _cell_angle_alpha 97.829(2) _cell_angle_beta 98.064(3) _cell_angle_gamma 103.501(3) _cell_volume 603.77(6) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C12 H8 Cl2 N1 O4 # Dc = 1.66 Fooo = 308.00 Mu = 5.46 M = 301.11 # Found Formula = C12 H9 Cl2 N1 O4 # Dc = 1.66 FOOO = 308.00 Mu = 5.46 M = 302.11 _chemical_formula_sum 'C24 H18 Cl4 N2 O8' _chemical_formula_moiety '(C6 Cl2 O4 H2), (C6 Cl2 O4), 2(C6 N1 H8)' _chemical_compound_source ? _chemical_formula_weight 604.22 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 200 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.546 # Sheldrick geometric approximatio 0.85 0.90 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8488 _exptl_absorpt_correction_T_max 0.8965 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q _computing_data_collection 'Nonius (1997-2001). COLLECT.' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 14333 _reflns_number_total 5250 _diffrn_reflns_av_R_equivalents 0.0455 # Number of reflections with Friedels Law is 5250 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5377 _diffrn_reflns_theta_min 1.556 _diffrn_reflns_theta_max 35.150 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 32.690 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -8 _reflns_limit_h_max 7 _reflns_limit_k_min -15 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.412 _refine_diff_density_max 0.512 _refine_ls_number_reflns 5250 _refine_ls_number_restraints 0 _refine_ls_number_parameters 208 #_refine_ls_R_factor_ref 0.0848 _refine_ls_wR_factor_ref 0.1151 _refine_ls_goodness_of_fit_ref 1.016 #_reflns_number_all 5250 _refine_ls_R_factor_all 0.0852 _refine_ls_wR_factor_all 0.1151 _reflns_threshold_expression >2\s(I) _reflns_number_gt 3510 _refine_ls_R_factor_gt 0.0438 _refine_ls_shift/su_max 0 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0408P)^2^+0.1704P] where P=(Fo^2^+2Fc^2^)/3' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 -0.1330(3) 0.40446(15) 0.40328(10) 0.0201(3) Uani d . 1 . . C C2 0.1317(3) 0.52502(15) 0.41285(11) 0.0205(3) Uani d . 1 . . C C3 0.2503(3) 0.61510(15) 0.51300(11) 0.0208(3) Uani d . 1 . . C Cl4 0.55238(8) 0.75197(4) 0.52221(3) 0.03111(10) Uani d . 1 . . Cl O5 0.2335(2) 0.54123(13) 0.33661(8) 0.0297(2) Uani d . 1 . . O O6 -0.2382(2) 0.32071(11) 0.31360(8) 0.0247(2) Uani d . 1 . . O C7 -0.0457(3) 0.41003(14) 0.07889(10) 0.0174(2) Uani d . 1 . . C C8 0.1192(3) 0.37343(15) -0.00508(10) 0.0177(2) Uani d . 1 . . C C9 -0.1532(3) 0.53214(15) 0.07920(10) 0.0179(2) Uani d . 1 . . C Cl10 -0.34870(7) 0.56955(4) 0.17123(3) 0.02291(9) Uani d . 1 . . Cl O11 0.2122(2) 0.26305(11) -0.00290(8) 0.0253(2) Uani d . 1 . . O O12 -0.0710(2) 0.32071(11) 0.14243(7) 0.0227(2) Uani d . 1 . . O C13 0.1303(3) -0.06254(16) 0.27802(11) 0.0221(3) Uani d . 1 . . C C14 0.0865(3) 0.06036(17) 0.23913(12) 0.0249(3) Uani d . 1 . . C N15 0.1992(3) 0.10183(14) 0.16004(10) 0.0267(3) Uani d . 1 . . N C16 0.3619(4) 0.02935(18) 0.11588(12) 0.0298(3) Uani d . 1 . . C C17 0.4116(3) -0.09532(18) 0.14976(12) 0.0279(3) Uani d . 1 . . C C18 0.2935(3) -0.14225(16) 0.23084(12) 0.0241(3) Uani d . 1 . . C C19 0.0040(4) -0.1066(2) 0.36756(13) 0.0326(4) Uani d . 1 . . C H141 -0.030(4) 0.117(2) 0.2652(15) 0.036(5) Uiso d . 1 . . H H161 0.435(4) 0.073(2) 0.0648(15) 0.035(5) Uiso d . 1 . . H H171 0.522(4) -0.146(2) 0.1182(15) 0.039(5) Uiso d . 1 . . H H181 0.327(4) -0.228(2) 0.2559(14) 0.034(5) Uiso d . 1 . . H H191 -0.096(5) -0.203(3) 0.3552(18) 0.059(7) Uiso d . 1 . . H H192 0.155(5) -0.091(3) 0.4280(18) 0.058(7) Uiso d . 1 . . H H193 -0.115(5) -0.047(3) 0.3838(17) 0.055(7) Uiso d . 1 . . H H8 0.158(5) 0.179(3) 0.1349(17) 0.052(6) Uiso d . 1 . . H H16 -0.158(5) 0.340(3) 0.254(2) 0.074(8) Uiso d . 1 . . H 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 0.0233(7) 0.0197(6) 0.0204(6) 0.0081(5) 0.0073(5) 0.0065(5) C2 0.0231(7) 0.0205(6) 0.0220(7) 0.0078(5) 0.0090(5) 0.0080(5) C3 0.0207(6) 0.0204(6) 0.0228(7) 0.0038(5) 0.0082(5) 0.0070(5) Cl4 0.02801(19) 0.0310(2) 0.0305(2) -0.00372(15) 0.01014(15) 0.00685(15) O5 0.0340(6) 0.0341(6) 0.0221(5) 0.0041(5) 0.0149(4) 0.0070(4) O6 0.0310(6) 0.0243(5) 0.0187(5) 0.0044(4) 0.0089(4) 0.0038(4) C7 0.0200(6) 0.0167(6) 0.0158(6) 0.0048(5) 0.0041(5) 0.0029(5) C8 0.0195(6) 0.0174(6) 0.0170(6) 0.0061(5) 0.0038(5) 0.0029(5) C9 0.0207(6) 0.0189(6) 0.0169(6) 0.0080(5) 0.0071(5) 0.0038(5) Cl10 0.02757(18) 0.02580(17) 0.02078(16) 0.01263(13) 0.01117(13) 0.00557(12) O11 0.0349(6) 0.0230(5) 0.0258(5) 0.0162(4) 0.0122(4) 0.0092(4) O12 0.0329(6) 0.0213(5) 0.0201(5) 0.0125(4) 0.0110(4) 0.0086(4) C13 0.0249(7) 0.0215(6) 0.0196(6) 0.0052(5) 0.0038(5) 0.0038(5) C14 0.0288(7) 0.0224(7) 0.0255(7) 0.0107(6) 0.0058(6) 0.0031(6) N15 0.0351(7) 0.0215(6) 0.0269(7) 0.0109(5) 0.0058(5) 0.0094(5) C16 0.0381(9) 0.0302(8) 0.0262(8) 0.0109(7) 0.0126(7) 0.0111(6) C17 0.0315(8) 0.0277(8) 0.0304(8) 0.0136(6) 0.0126(6) 0.0074(6) C18 0.0285(7) 0.0201(6) 0.0260(7) 0.0091(6) 0.0052(6) 0.0067(6) C19 0.0424(10) 0.0323(9) 0.0262(8) 0.0095(8) 0.0146(7) 0.0075(7) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 O6 . 1.3105(17) ? C1 C3 2_566 1.3566(18) ? C1 C2 . 1.514(2) ? C2 O5 . 1.2201(16) ? C2 C3 . 1.452(2) ? C3 C1 2_566 1.3566(18) ? C3 Cl4 . 1.7279(14) ? O6 H16 . 0.97(3) ? C7 O12 . 1.2739(16) ? C7 C9 . 1.3786(18) ? C7 C8 . 1.5410(18) ? C8 O11 . 1.2361(16) ? C8 C9 2_565 1.4222(18) ? C9 C8 2_565 1.4222(18) ? C9 Cl10 . 1.7354(13) ? C13 C14 . 1.380(2) ? C13 C18 . 1.396(2) ? C13 C19 . 1.500(2) ? C14 N15 . 1.335(2) ? C14 H141 . 0.96(2) ? N15 C16 . 1.334(2) ? N15 H8 . 0.90(2) ? C16 C17 . 1.375(2) ? C16 H161 . 0.922(19) ? C17 C18 . 1.388(2) ? C17 H171 . 0.93(2) ? C18 H181 . 0.957(19) ? C19 H191 . 0.91(2) ? C19 H192 . 1.00(2) ? C19 H193 . 0.94(2) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 C1 C3 122.34(13) . 2_566 ? O6 C1 C2 118.11(12) . . ? C3 C1 C2 119.54(13) 2_566 . ? O5 C2 C3 123.68(13) . . ? O5 C2 C1 118.57(13) . . ? C3 C2 C1 117.75(11) . . ? C1 C3 C2 122.71(13) 2_566 . ? C1 C3 Cl4 120.31(11) 2_566 . ? C2 C3 Cl4 116.98(10) . . ? C1 O6 H16 121.2(16) . . ? O12 C7 C9 125.84(12) . . ? O12 C7 C8 115.20(11) . . ? C9 C7 C8 118.96(11) . . ? O11 C8 C9 124.75(12) . 2_565 ? O11 C8 C7 117.08(11) . . ? C9 C8 C7 118.17(11) 2_565 . ? C7 C9 C8 122.87(12) . 2_565 ? C7 C9 Cl10 118.88(10) . . ? C8 C9 Cl10 118.21(10) 2_565 . ? C14 C13 C18 117.50(14) . . ? C14 C13 C19 120.19(14) . . ? C18 C13 C19 122.31(14) . . ? N15 C14 C13 120.96(14) . . ? N15 C14 H141 116.8(12) . . ? C13 C14 H141 122.2(12) . . ? C16 N15 C14 122.30(14) . . ? C16 N15 H8 119.6(15) . . ? C14 N15 H8 118.0(15) . . ? N15 C16 C17 119.91(15) . . ? N15 C16 H161 113.7(12) . . ? C17 C16 H161 126.4(12) . . ? C16 C17 C18 118.97(14) . . ? C16 C17 H171 119.6(12) . . ? C18 C17 H171 121.4(12) . . ? C17 C18 C13 120.32(14) . . ? C17 C18 H181 120.3(11) . . ? C13 C18 H181 119.4(11) . . ? C13 C19 H191 112.5(15) . . ? C13 C19 H192 108.9(14) . . ? H191 C19 H192 108.9(19) . . ? C13 C19 H193 109.8(14) . . ? H191 C19 H193 108(2) . . ? H192 C19 H193 108.6(19) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O6 C1 C2 O5 1.35(19) . . . . ? C3 C1 C2 O5 -179.74(13) 2_566 . . . ? O6 C1 C2 C3 -178.63(12) . . . . ? C3 C1 C2 C3 0.3(2) 2_566 . . . ? O5 C2 C3 C1 179.74(14) . . . 2_566 ? C1 C2 C3 C1 -0.3(2) . . . 2_566 ? O5 C2 C3 Cl4 0.0(2) . . . . ? C1 C2 C3 Cl4 179.98(10) . . . . ? O12 C7 C8 O11 -0.47(18) . . . . ? C9 C7 C8 O11 -179.94(13) . . . . ? O12 C7 C8 C9 179.42(12) . . . 2_565 ? C9 C7 C8 C9 0.0(2) . . . 2_565 ? O12 C7 C9 C8 -179.36(13) . . . 2_565 ? C8 C7 C9 C8 0.1(2) . . . 2_565 ? O12 C7 C9 Cl10 -1.6(2) . . . . ? C8 C7 C9 Cl10 177.85(10) . . . . ? C18 C13 C14 N15 -0.7(2) . . . . ? C19 C13 C14 N15 179.44(15) . . . . ? C13 C14 N15 C16 -1.1(2) . . . . ? C14 N15 C16 C17 2.0(3) . . . . ? N15 C16 C17 C18 -0.9(3) . . . . ? C16 C17 C18 C13 -0.9(2) . . . . ? C14 C13 C18 C17 1.7(2) . . . . ? C19 C13 C18 C17 -178.44(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N15 H8 O12 0.90(2) 1.95(2) 2.7381(16) 145(2) . N15 H8 O11 0.90(2) 2.13(2) 2.8241(16) 133.0(19) . O6 H16 O12 0.97(3) 1.62(3) 2.5569(14) 163(2) . _chemical_name_common '3-picoline chloranilate' data_3pic_1_1_300K _database_code_depnum_ccdc_archive 'CCDC 744790' _chemical_name_systematic '3-picoline chloranilate' _chemical_melting_point ? _cell_length_a 5.0718(2) _cell_length_b 9.4052(5) _cell_length_c 13.5038(8) _cell_angle_alpha 98.035(2) _cell_angle_beta 97.534(3) _cell_angle_gamma 103.372(3) _cell_volume 611.54(6) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C12 H8 Cl2 N1 O4 # Dc = 1.64 Fooo = 308.00 Mu = 5.39 M = 301.11 # Found Formula = C12 H9 Cl2 N1 O4 # Dc = 1.64 FOOO = 308.00 Mu = 5.39 M = 302.11 _chemical_formula_sum 'C24 H18 Cl4 N2 O8' _chemical_formula_moiety '(C6 Cl2 O4 H2), (C6 Cl2 O4), 2(C6 N1 H8)' _chemical_compound_source ? _chemical_formula_weight 604.22 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 300 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.641 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.539 # Sheldrick geometric approximatio 0.85 0.90 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8506 _exptl_absorpt_correction_T_max 0.8977 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q _computing_data_collection 'Nonius (1997-2001). COLLECT.' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 300 _diffrn_reflns_number 14639 _reflns_number_total 5269 _diffrn_reflns_av_R_equivalents 0.0509 # Number of reflections with Friedels Law is 5269 # Number of reflections without Friedels Law is 7869 # Theoretical number of reflections is about 5413 _diffrn_reflns_theta_min 1.545 _diffrn_reflns_theta_max 35.077 _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 35.08 _diffrn_measured_fraction_theta_full 0.973 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min -15 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.44 _refine_diff_density_max 0.489 _refine_ls_number_reflns 5269 _refine_ls_number_restraints 0 _refine_ls_number_parameters 208 #_refine_ls_R_factor_ref 0.0884 _refine_ls_wR_factor_ref 0.1261 _refine_ls_goodness_of_fit_ref 1.026 #_reflns_number_all 5269 _refine_ls_R_factor_all 0.122 _refine_ls_wR_factor_all 0.1423 _reflns_threshold_expression >2\s(I) _reflns_number_gt 2892 _refine_ls_R_factor_gt 0.0522 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.0927P] where P=(Fo^2^+2Fc^2^)/3' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 -0.1319(3) 0.40546(18) 0.40396(12) 0.0296(3) Uani d . 1 . . C C2 0.1298(3) 0.52630(18) 0.41294(13) 0.0308(4) Uani d . 1 . . C C3 0.2470(3) 0.61524(18) 0.51229(13) 0.0306(3) Uani d . 1 . . C Cl4 0.54587(10) 0.75228(6) 0.52113(4) 0.04918(15) Uani d . 1 . . Cl O5 0.2292(3) 0.54310(15) 0.33671(10) 0.0457(3) Uani d . 1 . . O O6 -0.2358(3) 0.32341(14) 0.31465(10) 0.0381(3) Uani d . 1 . . O C7 -0.0446(3) 0.41163(17) 0.07903(12) 0.0261(3) Uani d . 1 . . C C8 0.1203(3) 0.37449(17) -0.00473(12) 0.0264(3) Uani d . 1 . . C C9 -0.1534(3) 0.53225(17) 0.07873(12) 0.0264(3) Uani d . 1 . . C Cl10 -0.34787(9) 0.57082(5) 0.17083(3) 0.03466(12) Uani d . 1 . . Cl O11 0.2140(3) 0.26465(13) -0.00257(9) 0.0375(3) Uani d . 1 . . O O12 -0.0675(3) 0.32356(13) 0.14269(9) 0.0339(3) Uani d . 1 . . O C13 0.1280(4) -0.05971(19) 0.27719(13) 0.0326(4) Uani d . 1 . . C C14 0.0875(4) 0.0629(2) 0.23862(14) 0.0374(4) Uani d . 1 . . C N15 0.2012(3) 0.10402(18) 0.16018(12) 0.0396(4) Uani d . 1 . . N C16 0.3631(5) 0.0309(2) 0.11630(16) 0.0452(5) Uani d . 1 . . C C17 0.4090(4) -0.0939(2) 0.14943(16) 0.0421(4) Uani d . 1 . . C C18 0.2895(4) -0.1398(2) 0.22988(15) 0.0365(4) Uani d . 1 . . C C19 -0.0003(6) -0.1036(3) 0.36539(17) 0.0505(5) Uani d . 1 . . C H141 -0.028(5) 0.122(3) 0.2641(17) 0.053(6) Uiso d . 1 . . H H161 0.438(5) 0.073(3) 0.0651(17) 0.053(6) Uiso d . 1 . . H H171 0.525(4) -0.143(3) 0.1183(17) 0.051(6) Uiso d . 1 . . H H181 0.322(4) -0.227(2) 0.2542(16) 0.053(6) Uiso d . 1 . . H H191 -0.106(6) -0.198(3) 0.352(2) 0.088(10) Uiso d . 1 . . H H192 0.144(6) -0.085(3) 0.429(2) 0.096(10) Uiso d . 1 . . H H193 -0.104(6) -0.039(3) 0.385(2) 0.075(8) Uiso d . 1 . . H H8 0.160(4) 0.181(3) 0.1338(17) 0.054(6) Uiso d . 1 . . H H16 -0.145(6) 0.342(3) 0.248(2) 0.098(10) Uiso d . 1 . . H 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 0.0346(9) 0.0299(8) 0.0291(8) 0.0124(7) 0.0103(7) 0.0099(7) C2 0.0348(9) 0.0321(8) 0.0322(9) 0.0118(7) 0.0150(7) 0.0133(7) C3 0.0304(8) 0.0286(8) 0.0337(9) 0.0044(7) 0.0109(7) 0.0091(7) Cl4 0.0435(3) 0.0488(3) 0.0490(3) -0.0065(2) 0.0145(2) 0.0121(2) O5 0.0510(8) 0.0547(9) 0.0325(7) 0.0054(7) 0.0205(6) 0.0120(6) O6 0.0462(7) 0.0375(7) 0.0293(6) 0.0063(6) 0.0112(5) 0.0039(5) C7 0.0312(8) 0.0256(7) 0.0227(7) 0.0085(6) 0.0058(6) 0.0052(6) C8 0.0297(8) 0.0255(7) 0.0260(8) 0.0098(6) 0.0058(6) 0.0052(6) C9 0.0304(8) 0.0279(8) 0.0246(8) 0.0109(6) 0.0097(6) 0.0061(6) Cl10 0.0422(2) 0.0391(2) 0.0306(2) 0.01919(18) 0.01641(17) 0.00837(17) O11 0.0520(8) 0.0353(6) 0.0373(7) 0.0247(6) 0.0177(6) 0.0145(5) O12 0.0497(7) 0.0311(6) 0.0301(6) 0.0189(6) 0.0162(5) 0.0129(5) C13 0.0372(9) 0.0312(9) 0.0289(9) 0.0077(7) 0.0051(7) 0.0053(7) C14 0.0437(10) 0.0347(9) 0.0375(10) 0.0177(8) 0.0083(8) 0.0047(8) N15 0.0544(10) 0.0323(8) 0.0381(9) 0.0180(7) 0.0086(7) 0.0136(7) C16 0.0589(13) 0.0447(11) 0.0412(11) 0.0185(10) 0.0207(10) 0.0178(9) C17 0.0480(11) 0.0421(11) 0.0464(11) 0.0223(9) 0.0198(9) 0.0121(9) C18 0.0423(10) 0.0314(9) 0.0399(10) 0.0141(8) 0.0078(8) 0.0110(8) C19 0.0667(15) 0.0494(13) 0.0390(12) 0.0138(12) 0.0206(11) 0.0107(10) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 O6 . 1.309(2) ? C1 C3 2_566 1.356(2) ? C1 C2 . 1.513(2) ? C2 O5 . 1.2180(19) ? C2 C3 . 1.449(2) ? C3 C1 2_566 1.356(2) ? C3 Cl4 . 1.7261(16) ? O6 H16 . 1.09(3) ? C7 O12 . 1.2725(18) ? C7 C9 . 1.372(2) ? C7 C8 . 1.541(2) ? C8 O11 . 1.2353(19) ? C8 C9 2_565 1.420(2) ? C9 C8 2_565 1.420(2) ? C9 Cl10 . 1.7356(15) ? C13 C14 . 1.376(3) ? C13 C18 . 1.391(3) ? C13 C19 . 1.493(3) ? C14 N15 . 1.333(2) ? C14 H141 . 0.96(2) ? N15 C16 . 1.332(3) ? N15 H8 . 0.90(2) ? C16 C17 . 1.370(3) ? C16 H161 . 0.93(2) ? C17 C18 . 1.385(3) ? C17 H171 . 0.93(2) ? C18 H181 . 0.96(2) ? C19 H191 . 0.90(3) ? C19 H192 . 1.02(3) ? C19 H193 . 0.93(3) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 C1 C3 122.70(16) . 2_566 ? O6 C1 C2 117.83(14) . . ? C3 C1 C2 119.46(15) 2_566 . ? O5 C2 C3 123.97(16) . . ? O5 C2 C1 118.34(16) . . ? C3 C2 C1 117.69(14) . . ? C1 C3 C2 122.85(15) 2_566 . ? C1 C3 Cl4 120.11(14) 2_566 . ? C2 C3 Cl4 117.04(12) . . ? C1 O6 H16 122.3(16) . . ? O12 C7 C9 126.12(14) . . ? O12 C7 C8 115.04(13) . . ? C9 C7 C8 118.84(13) . . ? O11 C8 C9 124.67(15) . 2_565 ? O11 C8 C7 117.16(14) . . ? C9 C8 C7 118.16(13) 2_565 . ? C7 C9 C8 123.00(14) . 2_565 ? C7 C9 Cl10 118.84(12) . . ? C8 C9 Cl10 118.15(12) 2_565 . ? C14 C13 C18 117.11(17) . . ? C14 C13 C19 120.51(19) . . ? C18 C13 C19 122.38(18) . . ? N15 C14 C13 121.34(17) . . ? N15 C14 H141 115.7(13) . . ? C13 C14 H141 122.9(13) . . ? C16 N15 C14 122.06(17) . . ? C16 N15 H8 118.9(15) . . ? C14 N15 H8 119.0(15) . . ? N15 C16 C17 119.89(18) . . ? N15 C16 H161 114.0(14) . . ? C17 C16 H161 126.1(14) . . ? C16 C17 C18 118.96(18) . . ? C16 C17 H171 118.6(14) . . ? C18 C17 H171 122.5(14) . . ? C17 C18 C13 120.59(17) . . ? C17 C18 H181 119.7(13) . . ? C13 C18 H181 119.7(13) . . ? C13 C19 H191 112.6(18) . . ? C13 C19 H192 110.9(17) . . ? H191 C19 H192 112(2) . . ? C13 C19 H193 109.7(17) . . ? H191 C19 H193 110(2) . . ? H192 C19 H193 101(2) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O6 C1 C2 O5 1.1(2) . . . . ? C3 C1 C2 O5 -179.84(16) 2_566 . . . ? O6 C1 C2 C3 -178.93(15) . . . . ? C3 C1 C2 C3 0.1(3) 2_566 . . . ? O5 C2 C3 C1 179.84(17) . . . 2_566 ? C1 C2 C3 C1 -0.2(3) . . . 2_566 ? O5 C2 C3 Cl4 -0.1(2) . . . . ? C1 C2 C3 Cl4 179.87(12) . . . . ? O12 C7 C8 O11 -0.1(2) . . . . ? C9 C7 C8 O11 -179.59(15) . . . . ? O12 C7 C8 C9 179.77(14) . . . 2_565 ? C9 C7 C8 C9 0.2(2) . . . 2_565 ? O12 C7 C9 C8 -179.73(16) . . . 2_565 ? C8 C7 C9 C8 -0.3(3) . . . 2_565 ? O12 C7 C9 Cl10 -1.4(2) . . . . ? C8 C7 C9 Cl10 178.08(11) . . . . ? C18 C13 C14 N15 -0.9(3) . . . . ? C19 C13 C14 N15 179.74(19) . . . . ? C13 C14 N15 C16 -1.2(3) . . . . ? C14 N15 C16 C17 2.3(3) . . . . ? N15 C16 C17 C18 -1.3(3) . . . . ? C16 C17 C18 C13 -0.8(3) . . . . ? C14 C13 C18 C17 1.8(3) . . . . ? C19 C13 C18 C17 -178.8(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N15 H8 O12 0.90(2) 1.97(2) 2.744(2) 144(2) . N15 H8 O11 0.90(2) 2.13(2) 2.835(2) 135(2) . O6 H16 O12 1.09(3) 1.52(3) 2.5770(16) 164(3) . _chemical_name_common '3-picoline chloranilate' # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment '3pic_2_1_Form1.cif' # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. data_3pic_2to1_100 _database_code_depnum_ccdc_archive 'CCDC 744791' _chemical_name_systematic 'bis(3-picoline) chloranilate' _chemical_melting_point ? _cell_length_a 8.642(4) _cell_length_b 9.687(4) _cell_length_c 10.279(5) _cell_angle_alpha 90 _cell_angle_beta 102.08(2) _cell_angle_gamma 90 _cell_volume 841.5(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C9 H6 Cl1 N1 O2 # Dc = 1.54 Fooo = 408.00 Mu = 4.13 M = 195.60 # Found Formula = C9 H8 Cl1 N1 O2 # Dc = 1.56 FOOO = 408.00 Mu = 4.14 M = 197.62 _chemical_formula_sum 'C18 H16 Cl2 N2 O4' _chemical_formula_moiety '2(C6 H8 N), (C6 Cl2 O4)' _chemical_compound_source ? _chemical_formula_weight 395.24 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 100 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.414 # Sheldrick geometric approximatio 0.92 0.92 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.92 _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 8224 _reflns_number_total 2566 _diffrn_reflns_av_R_equivalents 0.0275 # Number of reflections with Friedels Law is 2566 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2566 _diffrn_reflns_theta_min 3.199 _diffrn_reflns_theta_max 30.494 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.494 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.352 _refine_diff_density_max 0.587 _refine_ls_number_reflns 2566 _refine_ls_number_restraints 0 _refine_ls_number_parameters 150 #_refine_ls_R_factor_ref 0.0495 _refine_ls_wR_factor_ref 0.1280 _refine_ls_goodness_of_fit_ref 1.159 #_reflns_number_all 2562 _refine_ls_R_factor_all 0.047 _refine_ls_wR_factor_all 0.1280 _reflns_threshold_expression >2\s(I) _reflns_number_gt 2229 _refine_ls_R_factor_gt 0.039 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0701P)^2^+0.4549P] where P=(Fo^2^+2Fc^2^)/3' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.89220(18) 0.46064(16) 0.37743(15) 0.0136(3) Uani d . 1 . . C C2 0.85636(18) 0.58235(16) 0.46308(16) 0.0136(3) Uani d . 1 . . C C3 0.96843(18) 0.61237(16) 0.58137(16) 0.0135(3) Uani d . 1 . . C Cl1 0.92709(5) 0.74884(4) 0.67922(4) 0.01647(14) Uani d . 1 . . Cl O2 0.73185(14) 0.64601(13) 0.42327(13) 0.0191(3) Uani d . 1 . . O O1 0.78987(14) 0.43320(13) 0.27382(12) 0.0191(3) Uani d . 1 . . O C5 0.36160(18) 0.69295(16) 0.02038(16) 0.0138(3) Uani d . 1 . . C C6 0.22839(18) 0.61664(18) 0.03232(16) 0.0149(3) Uani d . 1 . . C C7 0.2417(2) 0.50263(19) 0.11549(18) 0.0194(3) Uani d . 1 . . C C8 0.3895(2) 0.46507(18) 0.18570(17) 0.0188(3) Uani d . 1 . . C N1 0.51665(17) 0.53877(16) 0.17441(14) 0.0174(3) Uani d . 1 . . N C4 0.50605(19) 0.64965(17) 0.09474(16) 0.0153(3) Uani d . 1 . . C C9 0.3524(2) 0.8136(2) -0.0708(2) 0.0206(4) Uani d . 1 . . C H6 0.129(3) 0.644(2) -0.021(2) 0.017(5) Uiso d . 1 . . H H7 0.151(3) 0.451(2) 0.122(2) 0.015(5) Uiso d . 1 . . H H8 0.408(4) 0.388(3) 0.250(3) 0.045(8) Uiso d . 1 . . H H4 0.602(3) 0.693(3) 0.091(2) 0.024(6) Uiso d . 1 . . H H93 0.440(6) 0.814(5) -0.118(5) 0.115(17) Uiso d . 1 . . H H92 0.365(5) 0.891(4) -0.025(4) 0.078(12) Uiso d . 1 . . H H91 0.255(6) 0.826(5) -0.117(5) 0.094(15) Uiso d . 1 . . H H1 0.616(3) 0.511(3) 0.218(3) 0.037(7) Uiso d . 1 . . H 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 0.0130(7) 0.0149(7) 0.0121(7) 0.0006(5) 0.0008(5) 0.0017(6) C2 0.0129(7) 0.0119(7) 0.0156(7) 0.0014(5) 0.0023(5) 0.0020(5) C3 0.0128(7) 0.0138(7) 0.0131(6) 0.0014(5) 0.0009(5) -0.0012(5) Cl1 0.0152(2) 0.0169(2) 0.0170(2) 0.00285(13) 0.00269(14) -0.00363(13) O2 0.0147(5) 0.0183(6) 0.0218(6) 0.0056(5) -0.0016(5) -0.0003(5) O1 0.0168(6) 0.0212(6) 0.0166(5) 0.0043(5) -0.0032(4) -0.0032(5) C5 0.0146(7) 0.0123(7) 0.0149(7) 0.0006(5) 0.0041(6) -0.0022(6) C6 0.0110(6) 0.0179(7) 0.0152(7) 0.0003(6) 0.0011(5) -0.0014(6) C7 0.0183(8) 0.0199(8) 0.0201(8) -0.0038(6) 0.0042(6) -0.0005(6) C8 0.0235(8) 0.0175(8) 0.0147(7) 0.0032(6) 0.0026(6) -0.0004(6) N1 0.0166(6) 0.0201(7) 0.0138(6) 0.0052(5) -0.0008(5) -0.0037(5) C4 0.0123(7) 0.0156(7) 0.0173(7) -0.0003(6) 0.0019(6) -0.0074(6) C9 0.0227(9) 0.0171(8) 0.0235(8) 0.0011(6) 0.0080(7) 0.0031(7) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 O1 . 1.262(2) ? C1 C3 3_766 1.384(2) ? C1 C2 . 1.541(2) ? C2 O2 . 1.2334(19) ? C2 C3 . 1.417(2) ? C3 C1 3_766 1.384(2) ? C3 Cl1 . 1.7428(17) ? C5 C4 . 1.385(2) ? C5 C6 . 1.395(2) ? C5 C9 . 1.490(2) ? C6 C7 . 1.387(2) ? C6 H6 . 0.96(2) ? C7 C8 . 1.378(3) ? C7 H7 . 0.95(2) ? C8 N1 . 1.336(2) ? C8 H8 . 0.99(3) ? N1 C4 . 1.342(2) ? N1 H1 . 0.92(3) ? C4 H4 . 0.94(3) ? C9 H93 . 0.98(6) ? C9 H92 . 0.88(4) ? C9 H91 . 0.88(5) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C3 124.17(15) . 3_766 ? O1 C1 C2 117.01(14) . . ? C3 C1 C2 118.82(13) 3_766 . ? O2 C2 C3 125.04(16) . . ? O2 C2 C1 117.30(14) . . ? C3 C2 C1 117.66(13) . . ? C1 C3 C2 123.52(15) 3_766 . ? C1 C3 Cl1 118.76(12) 3_766 . ? C2 C3 Cl1 117.72(12) . . ? C4 C5 C6 117.12(15) . . ? C4 C5 C9 120.54(15) . . ? C6 C5 C9 122.31(15) . . ? C7 C6 C5 120.86(15) . . ? C7 C6 H6 121.4(14) . . ? C5 C6 H6 117.7(14) . . ? C8 C7 C6 118.77(16) . . ? C8 C7 H7 121.2(14) . . ? C6 C7 H7 120.0(14) . . ? N1 C8 C7 120.18(17) . . ? N1 C8 H8 116.2(18) . . ? C7 C8 H8 123.5(18) . . ? C8 N1 C4 121.90(15) . . ? C8 N1 H1 120.0(18) . . ? C4 N1 H1 118.0(18) . . ? N1 C4 C5 121.17(15) . . ? N1 C4 H4 115.6(16) . . ? C5 C4 H4 123.2(16) . . ? C5 C9 H93 112(3) . . ? C5 C9 H92 110(3) . . ? H93 C9 H92 104(4) . . ? C5 C9 H91 112(3) . . ? H93 C9 H91 118(4) . . ? H92 C9 H91 100(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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 -1.3(2) . . . . ? C3 C1 C2 O2 179.49(15) 3_766 . . . ? O1 C1 C2 C3 178.55(15) . . . . ? C3 C1 C2 C3 -0.6(2) 3_766 . . . ? O2 C2 C3 C1 -179.47(16) . . . 3_766 ? C1 C2 C3 C1 0.7(3) . . . 3_766 ? O2 C2 C3 Cl1 0.5(2) . . . . ? C1 C2 C3 Cl1 -179.35(11) . . . . ? C4 C5 C6 C7 0.0(2) . . . . ? C9 C5 C6 C7 178.24(16) . . . . ? C5 C6 C7 C8 -0.5(3) . . . . ? C6 C7 C8 N1 0.8(3) . . . . ? C7 C8 N1 C4 -0.6(3) . . . . ? C8 N1 C4 C5 0.1(2) . . . . ? C6 C5 C4 N1 0.2(2) . . . . ? C9 C5 C4 N1 -178.07(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.92(3) 1.67(3) 2.580(2) 168(3) . N1 H1 O2 0.92(3) 2.51(3) 3.015(2) 115(2) . _chemical_name_common 'bis(3-picoline) chloranilate' data_3pic_2_1_200K _database_code_depnum_ccdc_archive 'CCDC 744792' _chemical_name_systematic 'bis(3-picoline) chloranilate' _chemical_melting_point ? _cell_length_a 8.668(4) _cell_length_b 9.737(4) _cell_length_c 10.376(5) _cell_angle_alpha 90 _cell_angle_beta 102.55(2) _cell_angle_gamma 90 _cell_volume 854.8(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C9 H6 Cl1 N1 O2 # Dc = 1.52 Fooo = 408.00 Mu = 4.07 M = 195.60 # Found Formula = C9 H8 Cl1 N1 O2 # Dc = 1.54 FOOO = 408.00 Mu = 4.08 M = 197.62 _chemical_formula_sum 'C18 H16 Cl2 N2 O4' _chemical_formula_moiety '2(C6 H8 N), (C6 Cl2 O4)' _chemical_compound_source ? _chemical_formula_weight 395.24 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 200 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.536 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.408 # Sheldrick geometric approximatio 0.92 0.92 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9217 _exptl_absorpt_correction_T_max 0.9217 _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 8391 _reflns_number_total 2613 _diffrn_reflns_av_R_equivalents 0.0255 # Number of reflections with Friedels Law is 2613 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2609 _diffrn_reflns_theta_min 3.190 _diffrn_reflns_theta_max 30.504 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.504 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.315 _refine_diff_density_max 0.315 _refine_ls_number_reflns 2613 _refine_ls_number_restraints 0 _refine_ls_number_parameters 150 #_refine_ls_R_factor_ref 0.0483 _refine_ls_wR_factor_ref 0.0997 _refine_ls_goodness_of_fit_ref 1.033 #_reflns_number_all 2609 _refine_ls_R_factor_all 0.0475 _refine_ls_wR_factor_all 0.0997 _reflns_threshold_expression >2\s(I) _reflns_number_gt 2193 _refine_ls_R_factor_gt 0.0385 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.2224P] where P=(Fo^2^+2Fc^2^)/3' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.89234(14) 0.46185(13) 0.37744(12) 0.0228(2) Uani d . 1 . . C C2 0.85744(14) 0.58263(13) 0.46263(12) 0.0225(2) Uani d . 1 . . C C3 0.96867(14) 0.61124(13) 0.58109(12) 0.0225(2) Uani d . 1 . . C Cl1 0.92772(4) 0.74624(3) 0.67848(3) 0.03041(12) Uani d . 1 . . Cl O2 0.73336(11) 0.64634(10) 0.42262(11) 0.0328(2) Uani d . 1 . . O O1 0.79026(12) 0.43519(11) 0.27422(10) 0.0336(2) Uani d . 1 . . O C5 0.36222(14) 0.69303(13) 0.02047(12) 0.0235(3) Uani d . 1 . . C C6 0.22964(15) 0.61737(15) 0.03148(14) 0.0277(3) Uani d . 1 . . C C7 0.24333(18) 0.50433(16) 0.11356(16) 0.0337(3) Uani d . 1 . . C C8 0.3899(2) 0.46755(16) 0.18442(15) 0.0338(3) Uani d . 1 . . C N1 0.51677(14) 0.54066(13) 0.17413(11) 0.0299(3) Uani d . 1 . . N C4 0.50614(15) 0.65016(14) 0.09491(13) 0.0264(3) Uani d . 1 . . C C9 0.3520(2) 0.81293(17) -0.07073(18) 0.0360(3) Uani d . 1 . . C H6 0.127(2) 0.6483(19) -0.0218(19) 0.039(5) Uiso d . 1 . . H H7 0.152(3) 0.453(2) 0.120(2) 0.050(6) Uiso d . 1 . . H H8 0.407(2) 0.393(2) 0.242(2) 0.052(6) Uiso d . 1 . . H H4 0.607(2) 0.692(2) 0.0934(18) 0.037(5) Uiso d . 1 . . H H93 0.432(4) 0.816(4) -0.109(4) 0.133(13) Uiso d . 1 . . H H92 0.362(5) 0.900(4) -0.021(5) 0.155(16) Uiso d . 1 . . H H91 0.254(5) 0.825(4) -0.121(4) 0.122(12) Uiso d . 1 . . H H1 0.622(3) 0.514(2) 0.219(3) 0.069(7) Uiso d . 1 . . H 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 0.0202(5) 0.0247(6) 0.0225(6) 0.0016(5) 0.0021(4) 0.0019(5) C2 0.0196(5) 0.0222(6) 0.0246(6) 0.0016(4) 0.0024(4) 0.0033(5) C3 0.0208(5) 0.0227(6) 0.0233(6) 0.0023(4) 0.0031(4) -0.0018(4) Cl1 0.02667(18) 0.03216(19) 0.03131(19) 0.00589(12) 0.00391(13) -0.00773(12) O2 0.0241(5) 0.0332(5) 0.0360(5) 0.0101(4) -0.0044(4) -0.0028(4) O1 0.0279(5) 0.0385(6) 0.0284(5) 0.0092(4) -0.0072(4) -0.0067(4) C5 0.0223(6) 0.0244(6) 0.0237(6) 0.0011(5) 0.0049(5) -0.0050(5) C6 0.0191(5) 0.0332(7) 0.0292(6) 0.0001(5) 0.0013(5) -0.0019(5) C7 0.0297(7) 0.0341(7) 0.0372(7) -0.0061(6) 0.0068(6) 0.0014(6) C8 0.0412(8) 0.0301(7) 0.0280(7) 0.0038(6) 0.0027(6) 0.0026(6) N1 0.0264(5) 0.0350(6) 0.0242(5) 0.0084(5) -0.0033(4) -0.0076(5) C4 0.0203(5) 0.0287(6) 0.0290(6) -0.0005(5) 0.0024(5) -0.0102(5) C9 0.0387(8) 0.0300(7) 0.0419(8) 0.0037(6) 0.0145(7) 0.0063(6) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 O1 . 1.2592(16) ? C1 C3 3_766 1.3848(17) ? C1 C2 . 1.5402(18) ? C2 O2 . 1.2328(15) ? C2 C3 . 1.4152(18) ? C3 C1 3_766 1.3848(17) ? C3 Cl1 . 1.7410(14) ? C5 C4 . 1.3814(18) ? C5 C6 . 1.3905(19) ? C5 C9 . 1.493(2) ? C6 C7 . 1.381(2) ? C6 H6 . 0.987(19) ? C7 C8 . 1.370(2) ? C7 H7 . 0.95(2) ? C8 N1 . 1.334(2) ? C8 H8 . 0.93(2) ? N1 C4 . 1.337(2) ? N1 H1 . 0.97(2) ? C4 H4 . 0.972(19) ? C9 H93 . 0.87(4) ? C9 H92 . 0.99(4) ? C9 H91 . 0.90(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C3 124.16(12) . 3_766 ? O1 C1 C2 117.15(11) . . ? C3 C1 C2 118.69(11) 3_766 . ? O2 C2 C3 124.97(12) . . ? O2 C2 C1 117.18(11) . . ? C3 C2 C1 117.84(11) . . ? C1 C3 C2 123.45(12) 3_766 . ? C1 C3 Cl1 118.75(10) 3_766 . ? C2 C3 Cl1 117.80(9) . . ? C4 C5 C6 117.13(13) . . ? C4 C5 C9 120.83(13) . . ? C6 C5 C9 122.01(13) . . ? C7 C6 C5 120.74(13) . . ? C7 C6 H6 122.3(11) . . ? C5 C6 H6 116.9(11) . . ? C8 C7 C6 118.99(14) . . ? C8 C7 H7 120.6(13) . . ? C6 C7 H7 120.4(13) . . ? N1 C8 C7 120.14(14) . . ? N1 C8 H8 116.8(13) . . ? C7 C8 H8 123.1(13) . . ? C8 N1 C4 121.80(12) . . ? C8 N1 H1 121.7(15) . . ? C4 N1 H1 116.4(15) . . ? N1 C4 C5 121.19(13) . . ? N1 C4 H4 113.9(11) . . ? C5 C4 H4 124.9(11) . . ? C5 C9 H93 112(3) . . ? C5 C9 H92 111(3) . . ? H93 C9 H92 103(3) . . ? C5 C9 H91 112(2) . . ? H93 C9 H91 119(3) . . ? H92 C9 H91 99(3) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 -1.27(18) . . . . ? C3 C1 C2 O2 179.47(12) 3_766 . . . ? O1 C1 C2 C3 178.08(12) . . . . ? C3 C1 C2 C3 -1.19(19) 3_766 . . . ? O2 C2 C3 C1 -179.47(13) . . . 3_766 ? C1 C2 C3 C1 1.2(2) . . . 3_766 ? O2 C2 C3 Cl1 0.18(18) . . . . ? C1 C2 C3 Cl1 -179.10(9) . . . . ? C4 C5 C6 C7 -0.1(2) . . . . ? C9 C5 C6 C7 177.95(14) . . . . ? C5 C6 C7 C8 0.0(2) . . . . ? C6 C7 C8 N1 0.3(2) . . . . ? C7 C8 N1 C4 -0.5(2) . . . . ? C8 N1 C4 C5 0.4(2) . . . . ? C6 C5 C4 N1 -0.10(19) . . . . ? C9 C5 C4 N1 -178.19(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.97(2) 1.64(2) 2.5852(18) 166(2) . N1 H1 O2 0.97(2) 2.49(3) 3.0213(19) 114.9(18) . _chemical_name_common 'bis(3-picoline) chloranilate' data_3pic_2_1_300K _database_code_depnum_ccdc_archive 'CCDC 744793' _chemical_name_systematic 'bis(3-picoline) chloranilate' _chemical_melting_point ? _cell_length_a 8.699(5) _cell_length_b 9.795(5) _cell_length_c 10.486(5) _cell_angle_alpha 90 _cell_angle_beta 103.09(2) _cell_angle_gamma 90 _cell_volume 870.3(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C9 H6 Cl1 N1 O2 # Dc = 1.49 Fooo = 408.00 Mu = 4.00 M = 195.60 # Found Formula = C9 H8 Cl1 N1 O2 # Dc = 1.51 FOOO = 408.00 Mu = 4.00 M = 197.62 _chemical_formula_sum 'C18 H16 Cl2 N2 O4' _chemical_formula_moiety '2(C6 H8 N), (C6 Cl2 O4)' _chemical_compound_source ? _chemical_formula_weight 395.24 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 300 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.400 # Sheldrick geometric approximatio 0.92 0.92 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9230 _exptl_absorpt_correction_T_max 0.9230 _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 300 _diffrn_reflns_number 8531 _reflns_number_total 2647 _diffrn_reflns_av_R_equivalents 0.0297 # Number of reflections with Friedels Law is 2647 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2652 _diffrn_reflns_theta_min 3.179 _diffrn_reflns_theta_max 30.487 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.487 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.295 _refine_diff_density_max 0.244 _refine_ls_number_reflns 2647 _refine_ls_number_restraints 0 _refine_ls_number_parameters 150 #_refine_ls_R_factor_ref 0.0645 _refine_ls_wR_factor_ref 0.1095 _refine_ls_goodness_of_fit_ref 1.059 #_reflns_number_all 2647 _refine_ls_R_factor_all 0.0637 _refine_ls_wR_factor_all 0.1095 _reflns_threshold_expression >2\s(I) _reflns_number_gt 1999 _refine_ls_R_factor_gt 0.0458 _refine_ls_shift/su_max 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+0.2243P] where P=(Fo^2^+2Fc^2^)/3' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.89271(18) 0.46299(16) 0.37777(15) 0.0350(3) Uani d . 1 . . C C2 0.85798(17) 0.58209(16) 0.46226(15) 0.0344(3) Uani d . 1 . . C C3 0.96874(17) 0.60977(16) 0.58075(15) 0.0346(3) Uani d . 1 . . C Cl1 0.92804(5) 0.74333(5) 0.67760(4) 0.04790(16) Uani d . 1 . . Cl O2 0.73433(14) 0.64616(13) 0.42185(13) 0.0504(3) Uani d . 1 . . O O1 0.79077(15) 0.43747(15) 0.27472(13) 0.0516(3) Uani d . 1 . . O C5 0.36265(18) 0.69301(17) 0.02009(16) 0.0359(3) Uani d . 1 . . C C6 0.23122(19) 0.6175(2) 0.03095(18) 0.0433(4) Uani d . 1 . . C C7 0.2449(2) 0.5060(2) 0.1119(2) 0.0527(5) Uani d . 1 . . C C8 0.3909(3) 0.4700(2) 0.1831(2) 0.0522(5) Uani d . 1 . . C N1 0.51703(18) 0.54268(16) 0.17364(14) 0.0456(4) Uani d . 1 . . N C4 0.50598(19) 0.65085(19) 0.09513(17) 0.0407(4) Uani d . 1 . . C C9 0.3520(3) 0.8118(2) -0.0708(3) 0.0562(5) Uani d . 1 . . C H6 0.133(3) 0.647(2) -0.022(2) 0.053(6) Uiso d . 1 . . H H7 0.153(3) 0.454(2) 0.121(3) 0.076(8) Uiso d . 1 . . H H8 0.409(3) 0.394(3) 0.238(3) 0.082(8) Uiso d . 1 . . H H4 0.607(3) 0.699(2) 0.092(2) 0.057(6) Uiso d . 1 . . H H93 0.440(5) 0.822(4) -0.104(4) 0.139(14) Uiso d . 1 . . H H92 0.348(5) 0.891(5) -0.021(5) 0.161(17) Uiso d . 1 . . H H91 0.252(6) 0.820(5) -0.125(5) 0.162(17) Uiso d . 1 . . H H1 0.623(3) 0.516(3) 0.222(3) 0.092(9) Uiso d . 1 . . H 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 0.0302(7) 0.0380(8) 0.0341(7) 0.0027(6) 0.0013(6) 0.0033(6) C2 0.0275(7) 0.0356(8) 0.0381(8) 0.0033(6) 0.0030(6) 0.0047(6) C3 0.0290(7) 0.0363(8) 0.0368(8) 0.0035(6) 0.0042(6) -0.0021(6) Cl1 0.0405(2) 0.0516(3) 0.0490(3) 0.00972(18) 0.00481(18) -0.01216(19) O2 0.0359(6) 0.0519(7) 0.0553(8) 0.0166(6) -0.0067(5) -0.0044(6) O1 0.0410(6) 0.0600(8) 0.0440(7) 0.0150(6) -0.0110(5) -0.0108(6) C5 0.0330(7) 0.0370(8) 0.0368(8) 0.0018(6) 0.0060(6) -0.0068(6) C6 0.0275(7) 0.0528(10) 0.0459(9) 0.0003(7) 0.0007(7) -0.0021(8) C7 0.0466(10) 0.0531(11) 0.0574(11) -0.0100(9) 0.0097(9) 0.0022(9) C8 0.0622(12) 0.0461(10) 0.0448(10) 0.0069(9) 0.0045(9) 0.0050(8) N1 0.0387(8) 0.0535(9) 0.0376(7) 0.0111(7) -0.0056(6) -0.0099(7) C4 0.0293(7) 0.0459(9) 0.0443(9) -0.0006(7) 0.0028(6) -0.0155(7) C9 0.0596(13) 0.0475(11) 0.0650(13) 0.0057(10) 0.0212(11) 0.0099(10) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 O1 . 1.258(2) ? C1 C3 3_766 1.383(2) ? C1 C2 . 1.536(2) ? C2 O2 . 1.2345(18) ? C2 C3 . 1.415(2) ? C3 C1 3_766 1.383(2) ? C3 Cl1 . 1.7410(17) ? C5 C4 . 1.378(2) ? C5 C6 . 1.388(2) ? C5 C9 . 1.494(3) ? C6 C7 . 1.372(3) ? C6 H6 . 0.96(2) ? C7 C8 . 1.366(3) ? C7 H7 . 0.97(3) ? C8 N1 . 1.330(3) ? C8 H8 . 0.93(3) ? N1 C4 . 1.332(3) ? N1 H1 . 0.98(3) ? C4 H4 . 1.00(2) ? C9 H93 . 0.92(4) ? C9 H92 . 0.94(5) ? C9 H91 . 0.92(5) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C3 124.22(16) . 3_766 ? O1 C1 C2 117.00(14) . . ? C3 C1 C2 118.78(14) 3_766 . ? O2 C2 C3 124.81(16) . . ? O2 C2 C1 117.27(14) . . ? C3 C2 C1 117.92(13) . . ? C1 C3 C2 123.29(15) 3_766 . ? C1 C3 Cl1 118.80(12) 3_766 . ? C2 C3 Cl1 117.91(12) . . ? C4 C5 C6 116.67(17) . . ? C4 C5 C9 120.99(17) . . ? C6 C5 C9 122.32(17) . . ? C7 C6 C5 121.16(17) . . ? C7 C6 H6 122.9(13) . . ? C5 C6 H6 115.9(13) . . ? C8 C7 C6 118.91(19) . . ? C8 C7 H7 119.6(16) . . ? C6 C7 H7 121.4(16) . . ? N1 C8 C7 120.10(19) . . ? N1 C8 H8 116.6(17) . . ? C7 C8 H8 123.3(17) . . ? C8 N1 C4 121.79(16) . . ? C8 N1 H1 121.0(17) . . ? C4 N1 H1 117.2(17) . . ? N1 C4 C5 121.37(16) . . ? N1 C4 H4 116.8(13) . . ? C5 C4 H4 121.8(13) . . ? C5 C9 H93 113(3) . . ? C5 C9 H92 107(3) . . ? H93 C9 H92 105(3) . . ? C5 C9 H91 112(3) . . ? H93 C9 H91 120(4) . . ? H92 C9 H91 97(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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 -1.5(2) . . . . ? C3 C1 C2 O2 179.12(15) 3_766 . . . ? O1 C1 C2 C3 178.02(15) . . . . ? C3 C1 C2 C3 -1.4(2) 3_766 . . . ? O2 C2 C3 C1 -179.09(16) . . . 3_766 ? C1 C2 C3 C1 1.4(3) . . . 3_766 ? O2 C2 C3 Cl1 0.3(2) . . . . ? C1 C2 C3 Cl1 -179.15(11) . . . . ? C4 C5 C6 C7 -0.5(3) . . . . ? C9 C5 C6 C7 177.77(19) . . . . ? C5 C6 C7 C8 0.3(3) . . . . ? C6 C7 C8 N1 0.2(3) . . . . ? C7 C8 N1 C4 -0.5(3) . . . . ? C8 N1 C4 C5 0.3(3) . . . . ? C6 C5 C4 N1 0.2(2) . . . . ? C9 C5 C4 N1 -178.07(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.98(3) 1.63(3) 2.591(2) 164(3) . N1 H1 O2 0.98(3) 2.46(3) 3.024(2) 117(2) . _chemical_name_common 'bis(3-picoline) chloranilate' # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment '3pic_2to1form2_100K_K_new.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 744794' _chemical_name_systematic 'bis(3-picoline) chloranilate' _chemical_melting_point ? _cell_length_a 12.0490(5) _cell_length_b 5.32600(10) _cell_length_c 13.5813(6) _cell_angle_alpha 90 _cell_angle_beta 96.958(2) _cell_angle_gamma 90 _cell_volume 865.13(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall ? 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_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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C9 H9 Cl1 N1 O2 # Dc = 1.52 Fooo = 408.00 Mu = 4.03 M = 198.63 # Found Formula = C9 H8 Cl1 N1 O2 # Dc = 1.52 FOOO = 408.00 Mu = 4.03 M = 197.62 _chemical_formula_sum 'C18 H16 Cl2 N2 O4' _chemical_formula_moiety '(C6 Cl2 O4), 2(C6 N1 H8)' _chemical_compound_source ? _chemical_formula_weight 395.24 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 100 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.403 # Sheldrick geometric approximatio 0.94 0.94 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9414 _exptl_absorpt_correction_T_max 0.9414 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q _computing_data_collection 'Nonius (1997-2001). COLLECT.' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 10507 _reflns_number_total 2520 _diffrn_reflns_av_R_equivalents 0.0901 # Number of reflections with Friedels Law is 2520 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2526 _diffrn_reflns_theta_min 2.135 _diffrn_reflns_theta_max 30.010 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.410 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -16 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.319 _refine_diff_density_max 0.515 _refine_ls_number_reflns 2520 _refine_ls_number_restraints 0 _refine_ls_number_parameters 150 #_refine_ls_R_factor_ref 0.0827 _refine_ls_wR_factor_ref 0.1127 _refine_ls_goodness_of_fit_ref 1.035 #_reflns_number_all 2520 _refine_ls_R_factor_all 0.0836 _refine_ls_wR_factor_all 0.1336 _reflns_threshold_expression >2\s(I) _reflns_number_gt 1779 _refine_ls_R_factor_gt 0.0473 _refine_ls_shift/su_max 0.001 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+0.6107P] where P=(Fo^2^+2Fc^2^)/3' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.11391(16) 1.0676(4) 0.99291(15) 0.0151(4) Uani d . 1 . . C C2 0.06998(16) 0.8614(3) 0.93780(14) 0.0147(4) Uani d . 1 . . C C3 -0.05245(16) 0.7846(3) 0.94691(14) 0.0147(4) Uani d . 1 . . C O4 -0.08814(12) 0.5959(2) 0.89923(10) 0.0185(3) Uani d . 1 . . O O5 0.11993(12) 0.7349(3) 0.87861(10) 0.0185(3) Uani d . 1 . . O Cl6 0.25166(4) 1.15647(9) 0.98209(4) 0.01920(15) Uani d . 1 . . Cl C7 -0.05779(16) 0.0031(4) 0.68654(14) 0.0168(4) Uani d . 1 . . C C8 -0.04826(17) 0.1933(4) 0.75628(15) 0.0174(4) Uani d . 1 . . C N9 0.04148(15) 0.3455(3) 0.76700(13) 0.0184(4) Uani d . 1 . . N C10 0.12565(18) 0.3211(4) 0.71153(16) 0.0196(4) Uani d . 1 . . C C11 0.12178(18) 0.1350(4) 0.64131(16) 0.0204(4) Uani d . 1 . . C C12 0.03020(17) -0.0250(4) 0.62922(15) 0.0187(4) Uani d . 1 . . C C13 -0.15952(19) -0.1624(4) 0.67410(19) 0.0229(5) Uani d . 1 . . C H81 -0.1038(19) 0.224(4) 0.7983(16) 0.017(5) Uiso d . 1 . . H H101 0.1850(18) 0.437(4) 0.7251(16) 0.020(6) Uiso d . 1 . . H H111 0.182(2) 0.120(4) 0.6015(17) 0.025(6) Uiso d . 1 . . H H121 0.026(2) -0.158(4) 0.5815(17) 0.024(6) Uiso d . 1 . . H H131 -0.145(2) -0.309(5) 0.6344(18) 0.028(7) Uiso d . 1 . . H H132 -0.180(2) -0.213(6) 0.739(2) 0.056(9) Uiso d . 1 . . H H133 -0.221(2) -0.077(5) 0.6378(19) 0.038(7) Uiso d . 1 . . H H6 0.044(3) 0.461(6) 0.813(2) 0.065(10) Uiso d . 1 . . H 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 0.0139(9) 0.0118(9) 0.0201(10) -0.0014(7) 0.0042(8) -0.0004(8) C2 0.0174(9) 0.0108(9) 0.0159(9) 0.0018(7) 0.0024(8) 0.0021(7) C3 0.0170(10) 0.0120(9) 0.0152(9) 0.0004(7) 0.0023(8) 0.0012(7) O4 0.0202(7) 0.0132(7) 0.0224(8) -0.0025(5) 0.0035(6) -0.0047(6) O5 0.0185(7) 0.0157(7) 0.0222(8) 0.0000(5) 0.0061(6) -0.0052(6) Cl6 0.0164(2) 0.0151(2) 0.0271(3) -0.00233(18) 0.00694(19) -0.0023(2) C7 0.0175(9) 0.0128(9) 0.0195(10) 0.0019(7) 0.0000(8) 0.0044(8) C8 0.0188(10) 0.0148(10) 0.0195(10) 0.0050(7) 0.0053(8) 0.0029(8) N9 0.0255(10) 0.0123(8) 0.0175(9) 0.0027(7) 0.0026(7) -0.0023(7) C10 0.0203(11) 0.0152(10) 0.0230(11) -0.0022(8) 0.0019(8) 0.0013(8) C11 0.0195(10) 0.0202(10) 0.0232(11) 0.0017(8) 0.0091(8) 0.0013(8) C12 0.0234(11) 0.0147(10) 0.0181(10) 0.0020(8) 0.0025(8) -0.0029(8) C13 0.0202(11) 0.0166(10) 0.0309(13) -0.0016(8) -0.0008(9) 0.0037(10) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 C2 . 1.396(3) ? C1 C3 3_577 1.408(3) ? C1 Cl6 . 1.7491(19) ? C2 O5 . 1.257(2) ? C2 C3 . 1.550(3) ? C3 O4 . 1.244(2) ? C3 C1 3_577 1.408(3) ? C7 C8 . 1.382(3) ? C7 C12 . 1.397(3) ? C7 C13 . 1.503(3) ? C8 N9 . 1.345(3) ? C8 H81 . 0.95(2) ? N9 C10 . 1.341(3) ? N9 H6 . 0.87(3) ? C10 C11 . 1.372(3) ? C10 H101 . 0.95(2) ? C11 C12 . 1.388(3) ? C11 H111 . 0.96(2) ? C12 H121 . 0.96(2) ? C13 H131 . 0.98(3) ? C13 H132 . 0.98(3) ? C13 H133 . 0.95(3) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C3 123.97(18) . 3_577 ? C2 C1 Cl6 118.01(15) . . ? C3 C1 Cl6 117.95(14) 3_577 . ? O5 C2 C1 125.78(18) . . ? O5 C2 C3 116.33(16) . . ? C1 C2 C3 117.86(16) . . ? O4 C3 C1 125.51(18) . 3_577 ? O4 C3 C2 116.37(16) . . ? C1 C3 C2 118.11(16) 3_577 . ? C8 C7 C12 117.05(19) . . ? C8 C7 C13 120.40(19) . . ? C12 C7 C13 122.6(2) . . ? N9 C8 C7 120.99(18) . . ? N9 C8 H81 116.6(14) . . ? C7 C8 H81 122.4(14) . . ? C10 N9 C8 122.25(18) . . ? C10 N9 H6 120(2) . . ? C8 N9 H6 117(2) . . ? N9 C10 C11 119.73(19) . . ? N9 C10 H101 115.7(14) . . ? C11 C10 H101 124.6(14) . . ? C10 C11 C12 119.0(2) . . ? C10 C11 H111 119.2(14) . . ? C12 C11 H111 121.8(14) . . ? C11 C12 C7 121.0(2) . . ? C11 C12 H121 120.4(15) . . ? C7 C12 H121 118.6(15) . . ? C7 C13 H131 109.1(14) . . ? C7 C13 H132 110.7(18) . . ? H131 C13 H132 111(2) . . ? C7 C13 H133 110.5(16) . . ? H131 C13 H133 106(2) . . ? H132 C13 H133 109(2) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C1 C2 O5 175.27(19) 3_577 . . . ? Cl6 C1 C2 O5 -1.6(3) . . . . ? C3 C1 C2 C3 -2.6(3) 3_577 . . . ? Cl6 C1 C2 C3 -179.50(13) . . . . ? O5 C2 C3 O4 4.0(2) . . . . ? C1 C2 C3 O4 -177.96(18) . . . . ? O5 C2 C3 C1 -175.63(17) . . . 3_577 ? C1 C2 C3 C1 2.4(3) . . . 3_577 ? C12 C7 C8 N9 0.8(3) . . . . ? C13 C7 C8 N9 -178.86(19) . . . . ? C7 C8 N9 C10 -0.2(3) . . . . ? C8 N9 C10 C11 -0.3(3) . . . . ? N9 C10 C11 C12 0.0(3) . . . . ? C10 C11 C12 C7 0.7(3) . . . . ? C8 C7 C12 C11 -1.1(3) . . . . ? C13 C7 C12 C11 178.58(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N9 H6 O4 0.87(3) 2.21(3) 2.850(2) 130(3) . N9 H6 O5 0.87(3) 1.89(3) 2.673(2) 149(3) . _chemical_name_common 'bis(3-picoline) chloranilate' # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment '3pic_hydrate.cif' data_100K _database_code_depnum_ccdc_archive 'CCDC 744795' _chemical_name_systematic '3-picoline chloranilate hemihydrate' _chemical_melting_point ? _cell_length_a 7.167(3) _cell_length_b 12.221(6) _cell_length_c 13.381(7) _cell_angle_alpha 71.414(16) _cell_angle_beta 86.29(2) _cell_angle_gamma 88.917(16) _cell_volume 1108.6(9) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C25 H25 Cl2 N2 O2 # Dc = 1.37 Fooo = 532.00 Mu = 3.18 M = 456.39 # Found Formula = C21 H19 Cl3 N2 O7 # Dc = 1.55 FOOO = 532.00 Mu = 4.61 M = 517.75 _chemical_formula_sum 'C42 H38 Cl6 N4 O14' _chemical_formula_moiety '4(C6 H8 N), 2(C6 H Cl2 O4), (C6 Cl2 O4), 2(H2 O)' _chemical_compound_source ? _chemical_formula_weight 1035.50 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 100 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.1 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.2 _exptl_crystal_density_diffrn 1.551 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.461 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 13680 _reflns_number_total 5069 _diffrn_reflns_av_R_equivalents 0.059 _diffrn_reflns_theta_min 3.138 _diffrn_reflns_theta_max 27.477 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.477 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min -14 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.44 _refine_diff_density_max 0.48 _refine_ls_number_reflns 5069 _refine_ls_number_restraints 0 _refine_ls_number_parameters 374 #_refine_ls_R_factor_ref 0.0715 _refine_ls_wR_factor_ref 0.1424 _refine_ls_goodness_of_fit_ref 1.035 #_reflns_number_all 5066 _refine_ls_R_factor_all 0.0753 _refine_ls_wR_factor_all 0.1045 _reflns_threshold_expression >2\s(I) _reflns_number_gt 3492 _refine_ls_R_factor_gt 0.0439 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0779P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.6460(4) 0.5496(2) 0.9185(2) 0.0142(5) Uani d . 1 . . C C2 0.6517(3) 0.5563(2) 1.0312(2) 0.0144(6) Uani d . 1 . . C C3 0.5039(4) 0.5084(2) 1.1049(2) 0.0165(6) Uani d . 1 . . C Cl1 0.50601(9) 0.51791(6) 1.23143(6) 0.02145(18) Uani d . 1 . . Cl O2 0.7913(3) 0.60531(16) 1.04897(16) 0.0199(4) Uani d . 1 . . O O1 0.7793(3) 0.59672(15) 0.85464(16) 0.0185(4) Uani d . 1 . . O C15 0.8686(4) 0.0621(2) 0.7565(2) 0.0167(6) Uani d . 1 . . C C14 0.8911(4) 0.1803(2) 0.7485(2) 0.0162(6) Uani d . 1 . . C C13 0.8527(4) 0.2708(2) 0.6444(2) 0.0175(6) Uani d . 1 . . C C12 0.8014(4) 0.2410(2) 0.5614(2) 0.0162(6) Uani d . 1 . . C C11 0.7806(4) 0.1207(2) 0.5684(2) 0.0161(6) Uani d . 1 . . C C10 0.8169(4) 0.0267(2) 0.6738(2) 0.0172(6) Uani d . 1 . . C O3 0.7952(3) -0.07688(16) 0.67621(17) 0.0232(5) Uani d . 1 . . O O4 0.7354(3) 0.08994(17) 0.49481(17) 0.0262(5) Uani d . 1 . . O Cl3 0.76311(10) 0.34551(6) 0.44251(6) 0.02245(19) Uani d . 1 . . Cl O5 0.8704(3) 0.37918(16) 0.63869(17) 0.0201(5) Uani d . 1 . . O O6 0.9391(3) 0.21527(16) 0.81962(16) 0.0218(5) Uani d . 1 . . O Cl2 0.90980(10) -0.03969(6) 0.87725(6) 0.02326(19) Uani d . 1 . . Cl C5 1.3539(4) 0.7877(2) 0.9419(2) 0.0158(6) Uani d . 1 . . C C6 1.4292(4) 0.8098(2) 0.8392(2) 0.0195(6) Uani d . 1 . . C C7 1.3324(4) 0.7799(2) 0.7654(3) 0.0214(6) Uani d . 1 . . C C8 1.1615(4) 0.7266(2) 0.7951(2) 0.0210(6) Uani d . 1 . . C N1 1.0931(3) 0.70287(19) 0.8951(2) 0.0173(5) Uani d . 1 . . N C4 1.1819(4) 0.7323(2) 0.9679(2) 0.0170(6) Uani d . 1 . . C C9 1.4513(5) 0.8223(3) 1.0238(3) 0.0253(7) Uani d . 1 . . C C17 0.6820(4) -0.1900(2) 0.3599(2) 0.0207(6) Uani d . 1 . . C C16 0.7032(4) -0.1201(3) 0.4215(3) 0.0211(6) Uani d . 1 . . C N2 0.7358(3) -0.1649(2) 0.5239(2) 0.0200(5) Uani d . 1 . . N C20 0.7500(4) -0.2800(3) 0.5725(3) 0.0227(6) Uani d . 1 . . C C19 0.7320(4) -0.3533(3) 0.5144(3) 0.0244(7) Uani d . 1 . . C C18 0.6967(4) -0.3089(3) 0.4084(3) 0.0225(6) Uani d . 1 . . C C21 0.6435(5) -0.1387(3) 0.2447(3) 0.0268(7) Uani d . 1 . . C O7 1.0114(3) 0.46853(17) 0.76513(17) 0.0199(4) Uani d . 1 . . O H9A 1.404(6) 0.887(4) 1.032(4) 0.051(12) Uiso d . 1 . . H H9B 1.581(6) 0.834(3) 1.002(4) 0.055(12) Uiso d . 1 . . H H9C 1.437(5) 0.769(3) 1.093(4) 0.048(11) Uiso d . 1 . . H H21A 0.494(7) -0.129(4) 0.237(4) 0.085(16) Uiso d . 1 . . H H21B 0.696(6) -0.188(4) 0.207(4) 0.064(14) Uiso d . 1 . . H H21C 0.702(5) -0.062(3) 0.216(3) 0.049(11) Uiso d . 1 . . H H72 1.086(5) 0.441(3) 0.815(4) 0.042(11) Uiso d . 1 . . H H71 0.931(7) 0.496(4) 0.790(4) 0.059(15) Uiso d . 1 . . H H61 1.543(5) 0.847(3) 0.818(3) 0.039(10) Uiso d . 1 . . H H7 1.382(5) 0.793(3) 0.703(3) 0.033(10) Uiso d . 1 . . H H8 1.090(4) 0.704(3) 0.750(3) 0.024(8) Uiso d . 1 . . H H4 1.138(4) 0.716(3) 1.039(3) 0.025(9) Uiso d . 1 . . H H16 0.697(4) -0.036(2) 0.390(2) 0.011(7) Uiso d . 1 . . H H20 0.780(4) -0.302(3) 0.648(3) 0.021(8) Uiso d . 1 . . H H19 0.733(4) -0.434(3) 0.548(3) 0.019(8) Uiso d . 1 . . H H18 0.683(4) -0.365(3) 0.369(3) 0.021(8) Uiso d . 1 . . H H5 0.916(5) 0.389(3) 0.688(4) 0.045(12) Uiso d . 1 . . H H1 0.989(4) 0.669(2) 0.913(3) 0.015(8) Uiso d . 1 . . H H2 0.776(6) -0.113(4) 0.563(4) 0.073(15) Uiso d . 1 . . H 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 0.0149(13) 0.0143(12) 0.0124(14) 0.0037(10) -0.0004(11) -0.0034(10) C2 0.0132(13) 0.0163(12) 0.0144(14) 0.0019(10) -0.0043(11) -0.0053(11) C3 0.0203(14) 0.0183(13) 0.0108(14) 0.0012(10) -0.0017(11) -0.0044(11) Cl1 0.0230(4) 0.0308(4) 0.0120(3) -0.0050(3) 0.0003(3) -0.0087(3) O2 0.0178(10) 0.0256(10) 0.0168(11) -0.0058(8) -0.0007(8) -0.0072(8) O1 0.0174(10) 0.0229(10) 0.0161(11) -0.0041(8) 0.0033(8) -0.0081(8) C15 0.0186(13) 0.0172(13) 0.0131(14) -0.0005(10) -0.0008(11) -0.0033(11) C14 0.0138(13) 0.0223(13) 0.0124(14) 0.0005(10) 0.0010(11) -0.0058(11) C13 0.0178(14) 0.0190(13) 0.0151(15) 0.0027(10) 0.0008(12) -0.0049(11) C12 0.0188(14) 0.0174(13) 0.0111(14) -0.0005(10) -0.0009(11) -0.0028(11) C11 0.0118(12) 0.0246(14) 0.0147(14) -0.0033(10) 0.0006(11) -0.0101(11) C10 0.0152(13) 0.0201(13) 0.0167(15) -0.0031(10) 0.0027(11) -0.0069(11) O3 0.0326(12) 0.0194(10) 0.0188(12) -0.0048(8) 0.0004(9) -0.0078(9) O4 0.0354(12) 0.0268(11) 0.0193(12) -0.0040(9) -0.0051(10) -0.0104(9) Cl3 0.0305(4) 0.0237(4) 0.0124(4) 0.0026(3) -0.0044(3) -0.0042(3) O5 0.0297(11) 0.0183(10) 0.0146(11) 0.0028(8) -0.0062(9) -0.0076(8) O6 0.0320(11) 0.0216(10) 0.0139(11) 0.0020(8) -0.0020(9) -0.0087(8) Cl2 0.0321(4) 0.0193(3) 0.0161(4) 0.0016(3) -0.0033(3) -0.0023(3) C5 0.0187(13) 0.0136(12) 0.0158(14) -0.0003(10) -0.0010(12) -0.0055(11) C6 0.0209(15) 0.0185(13) 0.0186(16) -0.0031(11) 0.0006(12) -0.0055(12) C7 0.0267(16) 0.0238(15) 0.0137(16) -0.0005(12) 0.0022(13) -0.0064(12) C8 0.0271(16) 0.0211(14) 0.0165(15) 0.0016(11) -0.0041(13) -0.0078(12) N1 0.0157(12) 0.0165(11) 0.0192(13) -0.0007(9) -0.0001(10) -0.0051(10) C4 0.0241(14) 0.0158(13) 0.0114(14) 0.0042(11) -0.0009(12) -0.0051(11) C9 0.0254(17) 0.0333(18) 0.0210(18) -0.0019(14) -0.0040(14) -0.0132(14) C17 0.0161(14) 0.0274(15) 0.0197(16) 0.0002(11) -0.0004(12) -0.0091(12) C16 0.0180(14) 0.0223(15) 0.0221(16) 0.0022(11) 0.0006(12) -0.0065(12) N2 0.0198(12) 0.0237(12) 0.0186(14) -0.0036(10) 0.0000(11) -0.0096(10) C20 0.0207(15) 0.0273(15) 0.0191(16) -0.0008(12) -0.0012(13) -0.0061(12) C19 0.0270(16) 0.0204(15) 0.0246(17) -0.0018(12) 0.0005(13) -0.0059(13) C18 0.0172(14) 0.0254(15) 0.0280(18) -0.0051(11) 0.0000(13) -0.0130(13) C21 0.0254(17) 0.0367(18) 0.0206(17) 0.0000(14) -0.0049(14) -0.0119(14) O7 0.0221(11) 0.0227(10) 0.0169(11) 0.0026(9) -0.0035(9) -0.0090(9) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 O1 . 1.255(3) ? C1 C3 2_667 1.403(4) ? C1 C2 . 1.538(4) ? C2 O2 . 1.250(3) ? C2 C3 . 1.399(4) ? C3 C1 2_667 1.403(4) ? C3 Cl1 . 1.735(3) ? C15 C10 . 1.383(4) ? C15 C14 . 1.425(4) ? C15 Cl2 . 1.735(3) ? C14 O6 . 1.231(3) ? C14 C13 . 1.515(4) ? C13 O5 . 1.310(3) ? C13 C12 . 1.349(4) ? C12 C11 . 1.452(4) ? C12 Cl3 . 1.728(3) ? C11 O4 . 1.224(3) ? C11 C10 . 1.543(4) ? C10 O3 . 1.268(3) ? O5 H5 . 0.80(4) ? C5 C4 . 1.387(4) ? C5 C6 . 1.388(4) ? C5 C9 . 1.508(4) ? C6 C7 . 1.384(4) ? C6 H61 . 0.93(4) ? C7 C8 . 1.373(4) ? C7 H7 . 0.85(4) ? C8 N1 . 1.336(4) ? C8 H8 . 0.93(3) ? N1 C4 . 1.341(4) ? N1 H1 . 0.84(3) ? C4 H4 . 0.94(4) ? C9 H9A . 0.89(4) ? C9 H9B . 0.96(4) ? C9 H9C . 0.95(4) ? C17 C16 . 1.379(4) ? C17 C18 . 1.395(4) ? C17 C21 . 1.509(4) ? C16 N2 . 1.339(4) ? C16 H16 . 0.98(3) ? N2 C20 . 1.353(4) ? N2 H2 . 1.00(5) ? C20 C19 . 1.373(4) ? C20 H20 . 0.99(3) ? C19 C18 . 1.385(5) ? C19 H19 . 0.94(3) ? C18 H18 . 0.99(3) ? C21 H21A . 1.08(5) ? C21 H21B . 0.97(5) ? C21 H21C . 0.98(4) ? O7 H72 . 0.86(4) ? O7 H71 . 0.77(5) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C3 125.2(3) . 2_667 ? O1 C1 C2 116.3(2) . . ? C3 C1 C2 118.5(2) 2_667 . ? O2 C2 C3 125.2(3) . . ? O2 C2 C1 116.0(2) . . ? C3 C2 C1 118.8(2) . . ? C2 C3 C1 122.6(3) . 2_667 ? C2 C3 Cl1 119.3(2) . . ? C1 C3 Cl1 118.0(2) 2_667 . ? C10 C15 C14 123.3(2) . . ? C10 C15 Cl2 119.9(2) . . ? C14 C15 Cl2 116.9(2) . . ? O6 C14 C15 125.2(2) . . ? O6 C14 C13 116.9(2) . . ? C15 C14 C13 117.8(2) . . ? O5 C13 C12 121.5(2) . . ? O5 C13 C14 117.2(2) . . ? C12 C13 C14 121.3(2) . . ? C13 C12 C11 121.2(2) . . ? C13 C12 Cl3 120.6(2) . . ? C11 C12 Cl3 118.2(2) . . ? O4 C11 C12 123.3(3) . . ? O4 C11 C10 118.1(2) . . ? C12 C11 C10 118.6(2) . . ? O3 C10 C15 126.1(3) . . ? O3 C10 C11 116.1(2) . . ? C15 C10 C11 117.8(2) . . ? C13 O5 H5 114(3) . . ? C4 C5 C6 117.5(3) . . ? C4 C5 C9 120.0(3) . . ? C6 C5 C9 122.4(3) . . ? C7 C6 C5 120.6(3) . . ? C7 C6 H61 119(2) . . ? C5 C6 H61 121(2) . . ? C8 C7 C6 119.3(3) . . ? C8 C7 H7 122(2) . . ? C6 C7 H7 119(2) . . ? N1 C8 C7 119.4(3) . . ? N1 C8 H8 117(2) . . ? C7 C8 H8 124(2) . . ? C8 N1 C4 122.7(3) . . ? C8 N1 H1 119(2) . . ? C4 N1 H1 118(2) . . ? N1 C4 C5 120.4(3) . . ? N1 C4 H4 125(2) . . ? C5 C4 H4 115(2) . . ? C5 C9 H9A 112(3) . . ? C5 C9 H9B 109(3) . . ? H9A C9 H9B 109(3) . . ? C5 C9 H9C 115(2) . . ? H9A C9 H9C 102(4) . . ? H9B C9 H9C 110(3) . . ? C16 C17 C18 117.4(3) . . ? C16 C17 C21 120.7(3) . . ? C18 C17 C21 121.9(3) . . ? N2 C16 C17 121.2(3) . . ? N2 C16 H16 118.9(18) . . ? C17 C16 H16 119.9(18) . . ? C16 N2 C20 122.3(3) . . ? C16 N2 H2 119(3) . . ? C20 N2 H2 117(3) . . ? N2 C20 C19 118.8(3) . . ? N2 C20 H20 114.4(18) . . ? C19 C20 H20 126.7(18) . . ? C20 C19 C18 119.9(3) . . ? C20 C19 H19 120(2) . . ? C18 C19 H19 120(2) . . ? C19 C18 C17 120.5(3) . . ? C19 C18 H18 117.5(18) . . ? C17 C18 H18 122.0(18) . . ? C17 C21 H21A 109(3) . . ? C17 C21 H21B 109(3) . . ? H21A C21 H21B 111(4) . . ? C17 C21 H21C 109(2) . . ? H21A C21 H21C 108(3) . . ? H21B C21 H21C 109(4) . . ? H72 O7 H71 106(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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 -1.9(3) . . . . ? C3 C1 C2 O2 177.6(2) 2_667 . . . ? O1 C1 C2 C3 178.1(2) . . . . ? C3 C1 C2 C3 -2.5(4) 2_667 . . . ? O2 C2 C3 C1 -177.5(2) . . . 2_667 ? C1 C2 C3 C1 2.6(4) . . . 2_667 ? O2 C2 C3 Cl1 1.3(4) . . . . ? C1 C2 C3 Cl1 -178.66(17) . . . . ? C10 C15 C14 O6 -179.0(3) . . . . ? Cl2 C15 C14 O6 0.8(4) . . . . ? C10 C15 C14 C13 1.1(4) . . . . ? Cl2 C15 C14 C13 -179.00(19) . . . . ? O6 C14 C13 O5 -1.1(4) . . . . ? C15 C14 C13 O5 178.7(2) . . . . ? O6 C14 C13 C12 179.2(3) . . . . ? C15 C14 C13 C12 -0.9(4) . . . . ? O5 C13 C12 C11 -179.5(3) . . . . ? C14 C13 C12 C11 0.1(4) . . . . ? O5 C13 C12 Cl3 1.7(4) . . . . ? C14 C13 C12 Cl3 -178.6(2) . . . . ? C13 C12 C11 O4 -179.6(3) . . . . ? Cl3 C12 C11 O4 -0.8(4) . . . . ? C13 C12 C11 C10 0.5(4) . . . . ? Cl3 C12 C11 C10 179.29(19) . . . . ? C14 C15 C10 O3 179.8(3) . . . . ? Cl2 C15 C10 O3 -0.1(4) . . . . ? C14 C15 C10 C11 -0.5(4) . . . . ? Cl2 C15 C10 C11 179.62(19) . . . . ? O4 C11 C10 O3 -0.5(4) . . . . ? C12 C11 C10 O3 179.4(2) . . . . ? O4 C11 C10 C15 179.8(3) . . . . ? C12 C11 C10 C15 -0.3(4) . . . . ? C4 C5 C6 C7 1.6(4) . . . . ? C9 C5 C6 C7 -177.9(3) . . . . ? C5 C6 C7 C8 -0.8(4) . . . . ? C6 C7 C8 N1 -1.1(4) . . . . ? C7 C8 N1 C4 2.2(4) . . . . ? C8 N1 C4 C5 -1.3(4) . . . . ? C6 C5 C4 N1 -0.6(4) . . . . ? C9 C5 C4 N1 178.9(2) . . . . ? C18 C17 C16 N2 -0.3(4) . . . . ? C21 C17 C16 N2 179.4(3) . . . . ? C17 C16 N2 C20 0.1(4) . . . . ? C16 N2 C20 C19 0.6(4) . . . . ? N2 C20 C19 C18 -1.1(5) . . . . ? C20 C19 C18 C17 0.9(5) . . . . ? C16 C17 C18 C19 -0.2(4) . . . . ? C21 C17 C18 C19 -179.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5 O7 0.80(4) 1.80(4) 2.553(3) 157(4) . N1 H1 O1 0.84(3) 2.07(3) 2.783(3) 142(3) . N1 H1 O2 0.84(3) 2.17(3) 2.880(3) 141(3) . O7 H72 O2 0.86(4) 1.99(4) 2.824(3) 164(4) 2_767 N2 H2 O3 1.00(5) 1.72(5) 2.649(3) 153(4) . N2 H2 O4 1.00(5) 2.37(4) 3.013(3) 121(3) . O7 H71 O1 0.77(5) 1.99(5) 2.738(3) 164(5) . _chemical_name_common '3-picoline chloranilate hemihydrate' data_200K _database_code_depnum_ccdc_archive 'CCDC 744796' _chemical_name_systematic '3-picoline chloranilate hemihydrate' _chemical_melting_point ? _cell_length_a 7.205(2) _cell_length_b 12.267(4) _cell_length_c 13.453(5) _cell_angle_alpha 71.274(13) _cell_angle_beta 86.638(16) _cell_angle_gamma 89.577(13) _cell_volume 1124.1(6) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C25 H25 Cl2 N2 O2 # Dc = 1.35 Fooo = 532.00 Mu = 3.14 M = 456.39 # Found Formula = C21 H19 Cl3 N2 O7 # Dc = 1.53 FOOO = 532.00 Mu = 4.54 M = 517.75 _chemical_formula_sum 'C42 H38 Cl6 N4 O14' _chemical_formula_moiety '4(C6 H8 N), 2(C6 H Cl2 O4), (C6 Cl2 O4), 2(H2 O)' _chemical_compound_source ? _chemical_formula_weight 1035.50 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 200 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.454 # Sheldrick geometric approximatio 0.93 0.96 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9341 _exptl_absorpt_correction_T_max 0.9556 _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 14954 _reflns_number_total 5150 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_theta_min 3.119 _diffrn_reflns_theta_max 27.483 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.483 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min -14 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.27 _refine_diff_density_max 0.33 _refine_ls_number_reflns 5150 _refine_ls_number_restraints 0 _refine_ls_number_parameters 350 #_refine_ls_R_factor_ref 0.0631 _refine_ls_wR_factor_ref 0.101 _refine_ls_goodness_of_fit_ref 1.078 #_reflns_number_all 5150 _refine_ls_R_factor_all 0.065 _refine_ls_wR_factor_all 0.0711 _reflns_threshold_expression >2\s(I) _reflns_number_gt 3633 _refine_ls_R_factor_gt 0.0392 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+0.3109P] where P=(Fo^2^+2Fc^2^)/3' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.6462(3) 0.54828(16) 0.91940(16) 0.0238(4) Uani d . 1 . . C C2 0.6531(3) 0.55580(16) 1.03118(16) 0.0242(4) Uani d . 1 . . C C3 0.5048(3) 0.50885(16) 1.10403(16) 0.0266(4) Uani d . 1 . . C Cl1 0.50829(8) 0.51901(5) 1.22968(4) 0.03770(15) Uani d . 1 . . Cl O2 0.7929(2) 0.60435(13) 1.04879(12) 0.0347(4) Uani d . 1 . . O O1 0.78002(19) 0.59418(12) 0.85600(12) 0.0324(3) Uani d . 1 . . O C15 0.8673(3) 0.06195(17) 0.75421(17) 0.0276(4) Uani d . 1 . . C C14 0.8888(3) 0.17908(17) 0.74721(17) 0.0264(4) Uani d . 1 . . C C13 0.8504(3) 0.26932(17) 0.64368(17) 0.0264(4) Uani d . 1 . . C C12 0.8005(3) 0.23973(17) 0.56068(17) 0.0275(4) Uani d . 1 . . C C11 0.7807(3) 0.12020(18) 0.56741(17) 0.0290(5) Uani d . 1 . . C C10 0.8164(3) 0.02667(17) 0.67222(17) 0.0289(5) Uani d . 1 . . C O3 0.7945(2) -0.07635(13) 0.67473(13) 0.0416(4) Uani d . 1 . . O O4 0.7358(3) 0.08995(14) 0.49401(14) 0.0458(4) Uani d . 1 . . O Cl3 0.76252(8) 0.34435(5) 0.44250(4) 0.03878(15) Uani d . 1 . . Cl O5 0.8690(2) 0.37754(12) 0.63873(13) 0.0346(4) Uani d . 1 . . O O6 0.9370(2) 0.21452(13) 0.81764(12) 0.0366(4) Uani d . 1 . . O Cl2 0.90875(9) -0.03981(5) 0.87463(5) 0.04106(16) Uani d . 1 . . Cl C5 1.3529(3) 0.78885(16) 0.94128(17) 0.0273(4) Uani d . 1 . . C C6 1.4266(3) 0.80963(18) 0.83917(19) 0.0319(5) Uani d . 1 . . C C7 1.3299(3) 0.7783(2) 0.7668(2) 0.0365(5) Uani d . 1 . . C C8 1.1608(3) 0.72419(19) 0.79736(19) 0.0348(5) Uani d . 1 . . C N1 1.0929(3) 0.70217(14) 0.89656(15) 0.0293(4) Uani d . 1 . . N C4 1.1827(3) 0.73337(17) 0.96762(18) 0.0283(5) Uani d . 1 . . C C9 1.4498(3) 0.8247(2) 1.0219(2) 0.0438(6) Uani d . 1 . . C H9A 1.3966 0.8947 1.0273 0.066 Uiso calc R 1 . . H H9B 1.5797 0.837 1.001 0.066 Uiso calc R 1 . . H H9C 1.435 0.7653 1.0888 0.066 Uiso calc R 1 . . H C17 0.6803(3) -0.1926(2) 0.36151(19) 0.0336(5) Uani d . 1 . . C C16 0.7022(3) -0.1220(2) 0.42187(19) 0.0337(5) Uani d . 1 . . C N2 0.7359(3) -0.16621(17) 0.52405(17) 0.0347(4) Uani d . 1 . . N C20 0.7514(3) -0.2794(2) 0.5727(2) 0.0380(5) Uani d . 1 . . C C19 0.7341(3) -0.3536(2) 0.5159(2) 0.0421(6) Uani d . 1 . . C C18 0.6983(3) -0.3099(2) 0.4113(2) 0.0395(6) Uani d . 1 . . C C21 0.6413(4) -0.1423(2) 0.2474(2) 0.0485(7) Uani d . 1 . . C H21A 0.5095 -0.1405 0.2403 0.073 Uiso calc R 1 . . H H21B 0.6982 -0.1887 0.2089 0.073 Uiso calc R 1 . . H H21C 0.6914 -0.0654 0.2202 0.073 Uiso calc R 1 . . H O7 1.0063(2) 0.46744(14) 0.76547(14) 0.0354(4) Uani d . 1 . . O H72 1.065(4) 0.441(2) 0.808(2) 0.053 Uiso d . 1 . . H H71 0.911(4) 0.500(2) 0.795(2) 0.053 Uiso d . 1 . . H H61 1.536(4) 0.843(2) 0.821(2) 0.053(8) Uiso d . 1 . . H H7 1.382(3) 0.790(2) 0.702(2) 0.044(7) Uiso d . 1 . . H H8 1.080(4) 0.698(2) 0.750(2) 0.066(9) Uiso d . 1 . . H H4 1.136(3) 0.7143(19) 1.037(2) 0.035(6) Uiso d . 1 . . H H16 0.688(3) -0.0430(19) 0.3913(19) 0.029(6) Uiso d . 1 . . H H20 0.785(4) -0.303(2) 0.651(2) 0.050(7) Uiso d . 1 . . H H19 0.743(4) -0.430(3) 0.547(2) 0.062(9) Uiso d . 1 . . H H18 0.679(3) -0.363(2) 0.371(2) 0.041(7) Uiso d . 1 . . H H5 0.914(4) 0.390(2) 0.693(3) 0.065(9) Uiso d . 1 . . H H1 0.980(4) 0.666(2) 0.914(2) 0.061(9) Uiso d . 1 . . H H2 0.759(4) -0.119(3) 0.563(3) 0.079(10) Uiso d . 1 . . H 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 0.0255(10) 0.0212(9) 0.0237(11) 0.0014(7) -0.0018(9) -0.0056(8) C2 0.0244(10) 0.0231(9) 0.0251(11) 0.0001(8) -0.0042(9) -0.0074(8) C3 0.0324(11) 0.0271(10) 0.0207(11) 0.0004(8) -0.0027(9) -0.0082(8) Cl1 0.0394(3) 0.0525(3) 0.0244(3) -0.0107(2) 0.0010(2) -0.0170(2) O2 0.0307(8) 0.0440(9) 0.0305(9) -0.0114(6) -0.0018(7) -0.0133(7) O1 0.0298(8) 0.0396(8) 0.0289(9) -0.0078(6) 0.0047(7) -0.0137(7) C15 0.0286(10) 0.0285(10) 0.0242(11) 0.0010(8) -0.0007(9) -0.0064(9) C14 0.0241(10) 0.0328(11) 0.0228(11) 0.0034(8) 0.0016(8) -0.0102(9) C13 0.0255(10) 0.0275(10) 0.0259(11) 0.0028(8) 0.0005(9) -0.0083(9) C12 0.0298(11) 0.0294(10) 0.0222(11) -0.0001(8) -0.0014(9) -0.0067(8) C11 0.0277(11) 0.0359(11) 0.0259(11) -0.0031(8) 0.0004(9) -0.0138(9) C10 0.0278(11) 0.0309(11) 0.0280(12) -0.0050(8) 0.0036(9) -0.0105(9) O3 0.0603(11) 0.0308(8) 0.0353(10) -0.0107(7) -0.0014(8) -0.0127(7) O4 0.0666(12) 0.0428(9) 0.0333(10) -0.0041(8) -0.0120(9) -0.0180(8) Cl3 0.0533(4) 0.0385(3) 0.0233(3) 0.0047(2) -0.0086(3) -0.0072(2) O5 0.0510(10) 0.0287(8) 0.0281(9) 0.0050(7) -0.0108(8) -0.0130(7) O6 0.0526(10) 0.0351(8) 0.0257(8) 0.0034(7) -0.0070(7) -0.0141(7) Cl2 0.0552(4) 0.0323(3) 0.0308(3) 0.0021(2) -0.0054(3) -0.0028(2) C5 0.0293(11) 0.0245(10) 0.0289(12) -0.0002(8) -0.0050(9) -0.0092(9) C6 0.0311(12) 0.0288(11) 0.0330(13) -0.0074(9) 0.0037(10) -0.0069(9) C7 0.0432(13) 0.0413(13) 0.0235(12) -0.0061(10) 0.0030(11) -0.0091(10) C8 0.0409(13) 0.0350(11) 0.0303(13) -0.0026(9) -0.0056(10) -0.0122(10) N1 0.0277(9) 0.0267(9) 0.0343(11) -0.0032(7) -0.0011(8) -0.0110(8) C4 0.0346(12) 0.0265(10) 0.0243(12) 0.0002(8) -0.0008(10) -0.0090(9) C9 0.0452(14) 0.0525(15) 0.0408(15) -0.0074(11) -0.0066(12) -0.0241(12) C17 0.0217(10) 0.0462(13) 0.0366(13) -0.0007(9) -0.0015(9) -0.0185(11) C16 0.0316(12) 0.0342(12) 0.0355(13) 0.0001(9) -0.0015(10) -0.0118(10) N2 0.0335(10) 0.0413(11) 0.0344(11) -0.0032(8) -0.0008(9) -0.0193(9) C20 0.0351(13) 0.0414(13) 0.0361(14) -0.0033(10) -0.0009(11) -0.0104(11) C19 0.0432(14) 0.0332(13) 0.0488(16) -0.0041(10) 0.0014(12) -0.0122(12) C18 0.0355(13) 0.0405(13) 0.0487(16) -0.0051(10) 0.0005(11) -0.0234(12) C21 0.0413(14) 0.0699(17) 0.0387(15) 0.0067(12) -0.0105(12) -0.0224(13) O7 0.0415(10) 0.0377(9) 0.0315(10) 0.0015(7) -0.0065(8) -0.0167(7) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 O1 . 1.256(2) ? C1 C3 2_667 1.403(3) ? C1 C2 . 1.539(3) ? C2 O2 . 1.246(2) ? C2 C3 . 1.399(3) ? C3 C1 2_667 1.403(3) ? C3 Cl1 . 1.736(2) ? C15 C10 . 1.376(3) ? C15 C14 . 1.418(3) ? C15 Cl2 . 1.739(2) ? C14 O6 . 1.230(2) ? C14 C13 . 1.514(3) ? C13 O5 . 1.315(2) ? C13 C12 . 1.348(3) ? C12 C11 . 1.447(3) ? C12 Cl3 . 1.728(2) ? C11 O4 . 1.221(3) ? C11 C10 . 1.540(3) ? C10 O3 . 1.264(2) ? O5 H5 . 0.87(3) ? C5 C4 . 1.378(3) ? C5 C6 . 1.388(3) ? C5 C9 . 1.502(3) ? C6 C7 . 1.380(3) ? C6 H61 . 0.88(3) ? C7 C8 . 1.368(3) ? C7 H7 . 0.89(3) ? C8 N1 . 1.337(3) ? C8 H8 . 1.02(3) ? N1 C4 . 1.338(3) ? N1 H1 . 0.91(3) ? C4 H4 . 0.92(3) ? C9 H9A . 0.96 ? C9 H9B . 0.96 ? C9 H9C . 0.96 ? C17 C16 . 1.380(3) ? C17 C18 . 1.387(3) ? C17 C21 . 1.502(3) ? C16 N2 . 1.342(3) ? C16 H16 . 0.93(2) ? N2 C20 . 1.338(3) ? N2 H2 . 0.91(3) ? C20 C19 . 1.374(4) ? C20 H20 . 1.04(3) ? C19 C18 . 1.375(4) ? C19 H19 . 0.90(3) ? C18 H18 . 0.99(3) ? C21 H21A . 0.96 ? C21 H21B . 0.96 ? C21 H21C . 0.96 ? O7 H72 . 0.72(3) ? O7 H71 . 0.93(3) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C3 125.1(2) . 2_667 ? O1 C1 C2 116.18(17) . . ? C3 C1 C2 118.74(18) 2_667 . ? O2 C2 C3 125.4(2) . . ? O2 C2 C1 116.17(18) . . ? C3 C2 C1 118.45(17) . . ? C2 C3 C1 122.76(19) . 2_667 ? C2 C3 Cl1 119.04(15) . . ? C1 C3 Cl1 118.19(16) 2_667 . ? C10 C15 C14 123.69(19) . . ? C10 C15 Cl2 119.83(16) . . ? C14 C15 Cl2 116.48(16) . . ? O6 C14 C15 125.95(19) . . ? O6 C14 C13 116.60(18) . . ? C15 C14 C13 117.45(18) . . ? O5 C13 C12 121.83(18) . . ? O5 C13 C14 116.76(18) . . ? C12 C13 C14 121.41(18) . . ? C13 C12 C11 121.14(18) . . ? C13 C12 Cl3 120.49(16) . . ? C11 C12 Cl3 118.35(16) . . ? O4 C11 C12 123.1(2) . . ? O4 C11 C10 118.38(18) . . ? C12 C11 C10 118.53(18) . . ? O3 C10 C15 126.0(2) . . ? O3 C10 C11 116.18(19) . . ? C15 C10 C11 117.77(18) . . ? C13 O5 H5 116.7(19) . . ? C4 C5 C6 117.3(2) . . ? C4 C5 C9 119.8(2) . . ? C6 C5 C9 122.9(2) . . ? C7 C6 C5 120.9(2) . . ? C7 C6 H61 120.2(19) . . ? C5 C6 H61 118.9(19) . . ? C8 C7 C6 119.1(2) . . ? C8 C7 H7 121.4(17) . . ? C6 C7 H7 119.3(17) . . ? N1 C8 C7 119.6(2) . . ? N1 C8 H8 115.7(18) . . ? C7 C8 H8 124.7(18) . . ? C8 N1 C4 122.3(2) . . ? C8 N1 H1 117.4(19) . . ? C4 N1 H1 120(2) . . ? N1 C4 C5 120.8(2) . . ? N1 C4 H4 121.1(15) . . ? C5 C4 H4 118.0(15) . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C16 C17 C18 116.7(2) . . ? C16 C17 C21 120.4(2) . . ? C18 C17 C21 122.9(2) . . ? N2 C16 C17 120.9(2) . . ? N2 C16 H16 120.2(14) . . ? C17 C16 H16 118.8(14) . . ? C20 N2 C16 122.6(2) . . ? C20 N2 H2 116(2) . . ? C16 N2 H2 121(2) . . ? N2 C20 C19 119.0(2) . . ? N2 C20 H20 115.7(14) . . ? C19 C20 H20 125.1(14) . . ? C20 C19 C18 119.2(2) . . ? C20 C19 H19 121(2) . . ? C18 C19 H19 120(2) . . ? C19 C18 C17 121.6(2) . . ? C19 C18 H18 119.4(14) . . ? C17 C18 H18 119.0(14) . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? H72 O7 H71 105(3) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 -1.6(2) . . . . ? C3 C1 C2 O2 177.88(17) 2_667 . . . ? O1 C1 C2 C3 178.23(17) . . . . ? C3 C1 C2 C3 -2.3(3) 2_667 . . . ? O2 C2 C3 C1 -177.80(18) . . . 2_667 ? C1 C2 C3 C1 2.4(3) . . . 2_667 ? O2 C2 C3 Cl1 1.0(3) . . . . ? C1 C2 C3 Cl1 -178.79(13) . . . . ? C10 C15 C14 O6 -178.7(2) . . . . ? Cl2 C15 C14 O6 1.4(3) . . . . ? C10 C15 C14 C13 0.9(3) . . . . ? Cl2 C15 C14 C13 -179.02(15) . . . . ? O6 C14 C13 O5 -1.1(3) . . . . ? C15 C14 C13 O5 179.29(18) . . . . ? O6 C14 C13 C12 178.64(19) . . . . ? C15 C14 C13 C12 -1.0(3) . . . . ? O5 C13 C12 C11 179.97(19) . . . . ? C14 C13 C12 C11 0.3(3) . . . . ? O5 C13 C12 Cl3 1.1(3) . . . . ? C14 C13 C12 Cl3 -178.54(15) . . . . ? C13 C12 C11 O4 -180.0(2) . . . . ? Cl3 C12 C11 O4 -1.1(3) . . . . ? C13 C12 C11 C10 0.5(3) . . . . ? Cl3 C12 C11 C10 179.37(15) . . . . ? C14 C15 C10 O3 -179.6(2) . . . . ? Cl2 C15 C10 O3 0.3(3) . . . . ? C14 C15 C10 C11 -0.2(3) . . . . ? Cl2 C15 C10 C11 179.80(15) . . . . ? O4 C11 C10 O3 -0.6(3) . . . . ? C12 C11 C10 O3 178.91(19) . . . . ? O4 C11 C10 C15 179.9(2) . . . . ? C12 C11 C10 C15 -0.6(3) . . . . ? C4 C5 C6 C7 1.6(3) . . . . ? C9 C5 C6 C7 -178.0(2) . . . . ? C5 C6 C7 C8 -1.2(3) . . . . ? C6 C7 C8 N1 -0.3(3) . . . . ? C7 C8 N1 C4 1.4(3) . . . . ? C8 N1 C4 C5 -1.0(3) . . . . ? C6 C5 C4 N1 -0.6(3) . . . . ? C9 C5 C4 N1 179.04(19) . . . . ? C18 C17 C16 N2 -1.1(3) . . . . ? C21 C17 C16 N2 179.6(2) . . . . ? C17 C16 N2 C20 0.5(3) . . . . ? C16 N2 C20 C19 0.7(3) . . . . ? N2 C20 C19 C18 -1.1(4) . . . . ? C20 C19 C18 C17 0.4(4) . . . . ? C16 C17 C18 C19 0.7(3) . . . . ? C21 C17 C18 C19 180.0(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5 O7 0.87(3) 1.73(3) 2.554(2) 158(3) . N1 H1 O1 0.91(3) 2.02(3) 2.790(2) 142(3) . N1 H1 O2 0.91(3) 2.12(3) 2.872(3) 139(3) . O7 H72 O2 0.72(3) 2.14(3) 2.847(2) 165(3) 2_767 N2 H2 O3 0.91(3) 1.78(4) 2.654(3) 159(3) . N2 H2 O4 0.91(3) 2.44(3) 3.037(3) 123(3) . O7 H71 O1 0.93(3) 1.84(3) 2.739(2) 163(2) . _chemical_name_common '3-picoline chloranilate hemihydrate' data_300K _database_code_depnum_ccdc_archive 'CCDC 744797' _chemical_name_systematic '3-picoline chloranilate hemihydrate' _chemical_melting_point ? _cell_length_a 7.257(6) _cell_length_b 12.299(9) _cell_length_c 13.5378(12) _cell_angle_alpha 71.11(3) _cell_angle_beta 87.03(4) _cell_angle_gamma 90.31(3) _cell_volume 1141.4(12) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C25 H25 Cl2 N2 O4 # Dc = 1.42 Fooo = 532.00 Mu = 3.20 M = 488.39 # Found Formula = C21 H19 Cl3 N2 O7 # Dc = 1.51 FOOO = 532.00 Mu = 4.48 M = 517.75 _chemical_formula_sum 'C42 H38 Cl6 N4 O14' _chemical_formula_moiety '4(C6 H8 N), 2(C6 H Cl2 O4), (C6 Cl2 O4), 2(H2 O)' _chemical_compound_source ? _chemical_formula_weight 1035.50 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 300 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.448 # Sheldrick geometric approximatio 0.94 0.96 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9351 _exptl_absorpt_correction_T_max 0.9562 _diffrn_measurement_device_type ; 'Rigaku R-AXIS RAPID IP Image Plate diffractometer' ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 300 _diffrn_reflns_number 14609 _reflns_number_total 5186 _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_theta_min 3.098 _diffrn_reflns_theta_max 27.498 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.023 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min -14 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.23 _refine_diff_density_max 0.22 _refine_ls_number_reflns 5186 _refine_ls_number_restraints 0 _refine_ls_number_parameters 350 #_refine_ls_R_factor_ref 0.0877 _refine_ls_wR_factor_ref 0.1309 _refine_ls_goodness_of_fit_ref 1.0276 #_reflns_number_all 5186 _refine_ls_R_factor_all 0.0891 _refine_ls_wR_factor_all 0.1309 _reflns_threshold_expression >2\s(I) _reflns_number_gt 3084 _refine_ls_R_factor_gt 0.0442 _refine_ls_shift/su_max 0.003 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.3262P] where P=(Fo^2^+2Fc^2^)/3' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.6453(3) 0.5476(2) 0.92028(19) 0.0391(6) Uani d . 1 . . C C2 0.6536(3) 0.5554(2) 1.03081(18) 0.0384(6) Uani d . 1 . . C C3 0.5061(3) 0.5090(2) 1.10244(18) 0.0400(6) Uani d . 1 . . C Cl1 0.51093(10) 0.51925(7) 1.22790(5) 0.0603(2) Uani d . 1 . . Cl O2 0.7943(2) 0.60312(18) 1.04845(14) 0.0547(5) Uani d . 1 . . O O1 0.7793(2) 0.59215(17) 0.85701(14) 0.0525(5) Uani d . 1 . . O C15 0.8652(4) 0.0616(2) 0.75273(19) 0.0436(6) Uani d . 1 . . C C14 0.8867(3) 0.1777(2) 0.74569(19) 0.0416(6) Uani d . 1 . . C C13 0.8482(3) 0.2677(2) 0.64256(19) 0.0402(6) Uani d . 1 . . C C12 0.7982(3) 0.2387(2) 0.55995(19) 0.0428(6) Uani d . 1 . . C C11 0.7790(4) 0.1199(2) 0.5666(2) 0.0456(6) Uani d . 1 . . C C10 0.8139(4) 0.0263(2) 0.6714(2) 0.0454(6) Uani d . 1 . . C O3 0.7927(3) -0.07617(18) 0.67367(16) 0.0670(6) Uani d . 1 . . O O4 0.7366(3) 0.08955(19) 0.49315(16) 0.0703(6) Uani d . 1 . . O Cl3 0.76058(11) 0.34273(7) 0.44259(5) 0.0614(2) Uani d . 1 . . Cl O5 0.8650(3) 0.37552(17) 0.63767(16) 0.0563(5) Uani d . 1 . . O O6 0.9341(3) 0.21362(17) 0.81564(14) 0.0574(5) Uani d . 1 . . O Cl2 0.90726(12) -0.03981(7) 0.87202(6) 0.0648(2) Uani d . 1 . . Cl C5 1.3506(4) 0.7894(2) 0.9412(2) 0.0442(6) Uani d . 1 . . C C6 1.4246(4) 0.8094(2) 0.8400(2) 0.0488(7) Uani d . 1 . . C C7 1.3260(5) 0.7769(3) 0.7696(2) 0.0583(8) Uani d . 1 . . C C8 1.1598(4) 0.7228(3) 0.7995(2) 0.0561(7) Uani d . 1 . . C N1 1.0917(3) 0.70164(19) 0.89814(18) 0.0465(5) Uani d . 1 . . N C4 1.1820(4) 0.7339(2) 0.9681(2) 0.0449(6) Uani d . 1 . . C C9 1.4501(5) 0.8266(3) 1.0208(3) 0.0686(9) Uani d . 1 . . C H9A 1.4219 0.9049 1.0132 0.103 Uiso calc R 1 . . H H9B 1.5808 0.8202 1.0097 0.103 Uiso calc R 1 . . H H9C 1.4109 0.7782 1.0899 0.103 Uiso calc R 1 . . H C17 0.6817(4) -0.1951(3) 0.3634(2) 0.0523(7) Uani d . 1 . . C C16 0.7022(4) -0.1240(3) 0.4227(2) 0.0530(7) Uani d . 1 . . C N2 0.7360(3) -0.1671(3) 0.5230(2) 0.0545(6) Uani d . 1 . . N C20 0.7518(4) -0.2795(3) 0.5728(3) 0.0592(8) Uani d . 1 . . C C19 0.7362(5) -0.3534(3) 0.5172(3) 0.0654(9) Uani d . 1 . . C C18 0.7007(4) -0.3117(3) 0.4129(3) 0.0622(8) Uani d . 1 . . C C21 0.6419(5) -0.1460(4) 0.2490(3) 0.0764(10) Uani d . 1 . . C H21A 0.5272 -0.1065 0.2423 0.115 Uiso calc R 1 . . H H21B 0.6337 -0.2073 0.2199 0.115 Uiso calc R 1 . . H H21C 0.7396 -0.0932 0.2123 0.115 Uiso calc R 1 . . H O7 1.0009(3) 0.46614(19) 0.76656(16) 0.0576(5) Uani d . 1 . . O H72 1.066(5) 0.443(3) 0.815(3) 0.086 Uiso d . 1 . . H H71 0.912(5) 0.495(3) 0.800(3) 0.086 Uiso d . 1 . . H H61 1.548(4) 0.841(2) 0.818(2) 0.048(7) Uiso d . 1 . . H H7 1.367(4) 0.795(3) 0.708(3) 0.072(10) Uiso d . 1 . . H H8 1.083(4) 0.694(3) 0.752(2) 0.064(9) Uiso d . 1 . . H H4 1.122(4) 0.717(3) 1.041(3) 0.070(9) Uiso d . 1 . . H H16 0.689(4) -0.044(3) 0.394(2) 0.051(8) Uiso d . 1 . . H H20 0.781(4) -0.304(3) 0.650(3) 0.077(10) Uiso d . 1 . . H H19 0.742(5) -0.427(4) 0.549(3) 0.093(13) Uiso d . 1 . . H H18 0.691(4) -0.372(3) 0.367(3) 0.086(11) Uiso d . 1 . . H H5 0.916(5) 0.389(3) 0.682(3) 0.089(13) Uiso d . 1 . . H H1 0.958(6) 0.668(4) 0.924(3) 0.125(15) Uiso d . 1 . . H H2 0.755(4) -0.124(3) 0.554(2) 0.057(10) Uiso d . 1 . . H 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 0.0398(14) 0.0366(14) 0.0396(13) -0.0010(11) -0.0060(11) -0.0100(11) C2 0.0377(13) 0.0396(14) 0.0386(13) 0.0005(11) -0.0060(10) -0.0130(11) C3 0.0436(14) 0.0435(15) 0.0345(12) -0.0021(11) -0.0051(10) -0.0147(11) Cl1 0.0637(5) 0.0813(6) 0.0404(4) -0.0170(4) -0.0023(3) -0.0263(4) O2 0.0476(11) 0.0710(14) 0.0472(11) -0.0181(10) -0.0055(8) -0.0215(10) O1 0.0476(11) 0.0632(13) 0.0476(11) -0.0161(9) 0.0038(8) -0.0206(10) C15 0.0464(15) 0.0445(16) 0.0381(14) -0.0001(12) -0.0006(11) -0.0112(12) C14 0.0418(14) 0.0482(16) 0.0358(13) 0.0034(12) -0.0011(10) -0.0150(12) C13 0.0404(14) 0.0450(16) 0.0383(13) 0.0052(11) 0.0007(10) -0.0183(12) C12 0.0465(15) 0.0485(16) 0.0327(13) 0.0000(12) -0.0045(10) -0.0120(12) C11 0.0434(15) 0.0521(17) 0.0445(15) -0.0055(12) -0.0014(11) -0.0203(13) C10 0.0457(15) 0.0483(17) 0.0446(15) -0.0062(12) 0.0031(11) -0.0196(13) O3 0.0987(17) 0.0485(13) 0.0553(13) -0.0144(11) -0.0019(11) -0.0195(10) O4 0.1016(17) 0.0649(14) 0.0542(12) -0.0053(12) -0.0212(11) -0.0305(11) Cl3 0.0828(5) 0.0600(5) 0.0395(4) 0.0076(4) -0.0160(3) -0.0115(3) O5 0.0833(15) 0.0437(12) 0.0466(11) 0.0066(10) -0.0180(10) -0.0190(10) O6 0.0815(14) 0.0543(12) 0.0415(10) 0.0046(10) -0.0146(9) -0.0206(9) Cl2 0.0852(6) 0.0518(5) 0.0491(4) 0.0040(4) -0.0100(4) -0.0041(3) C5 0.0479(15) 0.0392(15) 0.0467(15) -0.0041(12) -0.0087(12) -0.0147(12) C6 0.0477(17) 0.0492(17) 0.0477(16) -0.0120(13) 0.0050(12) -0.0146(13) C7 0.069(2) 0.064(2) 0.0397(16) -0.0123(16) 0.0062(14) -0.0149(15) C8 0.0611(19) 0.0605(19) 0.0520(17) -0.0053(15) -0.0105(14) -0.0247(15) N1 0.0439(13) 0.0423(13) 0.0542(14) -0.0041(10) -0.0042(10) -0.0168(11) C4 0.0507(16) 0.0420(15) 0.0416(14) -0.0038(12) -0.0008(12) -0.0134(12) C9 0.072(2) 0.082(2) 0.065(2) -0.0124(18) -0.0100(16) -0.0402(19) C17 0.0381(15) 0.068(2) 0.0563(17) -0.0026(14) -0.0049(12) -0.0271(16) C16 0.0486(17) 0.0520(19) 0.0595(19) 0.0019(14) -0.0057(13) -0.0190(16) N2 0.0527(15) 0.0639(18) 0.0569(16) -0.0048(12) -0.0041(11) -0.0335(15) C20 0.0578(19) 0.063(2) 0.0554(19) -0.0052(15) -0.0039(14) -0.0167(17) C19 0.068(2) 0.052(2) 0.075(2) -0.0035(17) -0.0031(17) -0.0192(19) C18 0.0566(19) 0.064(2) 0.075(2) -0.0068(16) -0.0039(15) -0.0355(19) C21 0.062(2) 0.109(3) 0.062(2) 0.005(2) -0.0145(16) -0.030(2) O7 0.0676(14) 0.0600(14) 0.0529(12) -0.0009(11) -0.0105(10) -0.0276(11) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; 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 C1 O1 . 1.259(3) ? C1 C3 2_667 1.397(3) ? C1 C2 . 1.534(3) ? C2 O2 . 1.247(3) ? C2 C3 . 1.393(4) ? C3 C1 2_667 1.397(3) ? C3 Cl1 . 1.745(2) ? C15 C10 . 1.375(4) ? C15 C14 . 1.407(4) ? C15 Cl2 . 1.734(3) ? C14 O6 . 1.230(3) ? C14 C13 . 1.515(4) ? C13 O5 . 1.311(3) ? C13 C12 . 1.345(3) ? C12 C11 . 1.440(4) ? C12 Cl3 . 1.723(3) ? C11 O4 . 1.222(3) ? C11 C10 . 1.544(4) ? C10 O3 . 1.259(3) ? O5 H5 . 0.79(4) ? C5 C4 . 1.370(4) ? C5 C6 . 1.390(4) ? C5 C9 . 1.512(4) ? C6 C7 . 1.377(4) ? C6 H61 . 0.97(3) ? C7 C8 . 1.351(4) ? C7 H7 . 0.83(3) ? C8 N1 . 1.342(4) ? C8 H8 . 1.02(3) ? N1 C4 . 1.338(3) ? N1 H1 . 1.05(5) ? C4 H4 . 1.01(3) ? C9 H9A . 0.96 ? C9 H9B . 0.96 ? C9 H9C . 0.96 ? C17 C16 . 1.378(4) ? C17 C18 . 1.384(5) ? C17 C21 . 1.512(4) ? C16 N2 . 1.325(4) ? C16 H16 . 0.94(3) ? N2 C20 . 1.336(4) ? N2 H2 . 0.79(3) ? C20 C19 . 1.363(5) ? C20 H20 . 1.02(3) ? C19 C18 . 1.376(5) ? C19 H19 . 0.87(4) ? C18 H18 . 1.11(4) ? C21 H21A . 0.96 ? C21 H21B . 0.96 ? C21 H21C . 0.96 ? O7 H72 . 0.81(4) ? O7 H71 . 0.91(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C3 125.0(2) . 2_667 ? O1 C1 C2 116.4(2) . . ? C3 C1 C2 118.6(2) 2_667 . ? O2 C2 C3 125.6(2) . . ? O2 C2 C1 116.3(2) . . ? C3 C2 C1 118.1(2) . . ? C2 C3 C1 123.3(2) . 2_667 ? C2 C3 Cl1 118.83(19) . . ? C1 C3 Cl1 117.88(19) 2_667 . ? C10 C15 C14 123.7(2) . . ? C10 C15 Cl2 119.7(2) . . ? C14 C15 Cl2 116.60(19) . . ? O6 C14 C15 126.1(2) . . ? O6 C14 C13 116.5(2) . . ? C15 C14 C13 117.4(2) . . ? O5 C13 C12 121.4(2) . . ? O5 C13 C14 116.8(2) . . ? C12 C13 C14 121.8(2) . . ? C13 C12 C11 120.8(2) . . ? C13 C12 Cl3 120.8(2) . . ? C11 C12 Cl3 118.34(19) . . ? O4 C11 C12 123.1(3) . . ? O4 C11 C10 118.4(3) . . ? C12 C11 C10 118.6(2) . . ? O3 C10 C15 126.2(3) . . ? O3 C10 C11 116.1(2) . . ? C15 C10 C11 117.7(2) . . ? C13 O5 H5 118(3) . . ? C4 C5 C6 117.9(2) . . ? C4 C5 C9 120.0(3) . . ? C6 C5 C9 122.1(3) . . ? C7 C6 C5 119.8(3) . . ? C7 C6 H61 118.3(15) . . ? C5 C6 H61 121.7(15) . . ? C8 C7 C6 120.2(3) . . ? C8 C7 H7 121(2) . . ? C6 C7 H7 119(2) . . ? N1 C8 C7 119.4(3) . . ? N1 C8 H8 116.7(17) . . ? C7 C8 H8 123.9(17) . . ? C4 N1 C8 122.0(3) . . ? C4 N1 H1 115(2) . . ? C8 N1 H1 123(2) . . ? N1 C4 C5 120.6(3) . . ? N1 C4 H4 118.2(18) . . ? C5 C4 H4 121.2(18) . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C16 C17 C18 117.0(3) . . ? C16 C17 C21 120.7(3) . . ? C18 C17 C21 122.3(3) . . ? N2 C16 C17 120.6(3) . . ? N2 C16 H16 118.3(17) . . ? C17 C16 H16 121.0(17) . . ? C16 N2 C20 123.3(3) . . ? C16 N2 H2 119(2) . . ? C20 N2 H2 118(2) . . ? N2 C20 C19 118.4(3) . . ? N2 C20 H20 117.0(19) . . ? C19 C20 H20 124.5(19) . . ? C20 C19 C18 119.9(4) . . ? C20 C19 H19 120(3) . . ? C18 C19 H19 120(3) . . ? C19 C18 C17 120.7(3) . . ? C19 C18 H18 119.8(18) . . ? C17 C18 H18 119.5(18) . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? H72 O7 H71 97(3) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 -1.4(3) . . . . ? C3 C1 C2 O2 177.6(2) 2_667 . . . ? O1 C1 C2 C3 178.7(2) . . . . ? C3 C1 C2 C3 -2.2(4) 2_667 . . . ? O2 C2 C3 C1 -177.5(2) . . . 2_667 ? C1 C2 C3 C1 2.3(4) . . . 2_667 ? O2 C2 C3 Cl1 1.3(4) . . . . ? C1 C2 C3 Cl1 -178.88(17) . . . . ? C10 C15 C14 O6 -179.1(3) . . . . ? Cl2 C15 C14 O6 0.8(4) . . . . ? C10 C15 C14 C13 0.8(4) . . . . ? Cl2 C15 C14 C13 -179.26(17) . . . . ? O6 C14 C13 O5 -1.5(3) . . . . ? C15 C14 C13 O5 178.6(2) . . . . ? O6 C14 C13 C12 179.0(2) . . . . ? C15 C14 C13 C12 -1.0(4) . . . . ? O5 C13 C12 C11 -179.6(2) . . . . ? C14 C13 C12 C11 0.0(4) . . . . ? O5 C13 C12 Cl3 2.0(4) . . . . ? C14 C13 C12 Cl3 -178.46(18) . . . . ? C13 C12 C11 O4 -178.9(3) . . . . ? Cl3 C12 C11 O4 -0.4(4) . . . . ? C13 C12 C11 C10 1.1(4) . . . . ? Cl3 C12 C11 C10 179.58(18) . . . . ? C14 C15 C10 O3 -180.0(3) . . . . ? Cl2 C15 C10 O3 0.1(4) . . . . ? C14 C15 C10 C11 0.3(4) . . . . ? Cl2 C15 C10 C11 -179.68(18) . . . . ? O4 C11 C10 O3 -1.1(4) . . . . ? C12 C11 C10 O3 179.0(2) . . . . ? O4 C11 C10 C15 178.7(2) . . . . ? C12 C11 C10 C15 -1.2(4) . . . . ? C4 C5 C6 C7 2.0(4) . . . . ? C9 C5 C6 C7 -178.1(3) . . . . ? C5 C6 C7 C8 -1.8(5) . . . . ? C6 C7 C8 N1 0.2(5) . . . . ? C7 C8 N1 C4 1.1(5) . . . . ? C8 N1 C4 C5 -0.8(4) . . . . ? C6 C5 C4 N1 -0.8(4) . . . . ? C9 C5 C4 N1 179.3(3) . . . . ? C18 C17 C16 N2 -0.9(4) . . . . ? C21 C17 C16 N2 179.6(3) . . . . ? C17 C16 N2 C20 -0.2(4) . . . . ? C16 N2 C20 C19 1.4(5) . . . . ? N2 C20 C19 C18 -1.5(5) . . . . ? C20 C19 C18 C17 0.4(5) . . . . ? C16 C17 C18 C19 0.8(4) . . . . ? C21 C17 C18 C19 -179.8(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5 O7 0.79(4) 1.83(4) 2.586(3) 161(4) . N1 H1 O1 1.05(5) 2.01(4) 2.802(3) 130(3) . N1 H1 O2 1.05(5) 1.95(5) 2.861(3) 143(3) . O7 H72 O2 0.81(4) 2.07(4) 2.868(3) 171(4) 2_767 N2 H2 O3 0.79(3) 1.92(3) 2.672(3) 158(3) . N2 H2 O4 0.79(3) 2.50(3) 3.050(4) 128(3) . O7 H71 O1 0.91(4) 1.87(4) 2.746(3) 163(4) . _chemical_name_common '3-picoline chloranilate hemihydrate'