#------------------------------------------------------------------------------ #$Date: 2012-12-21 08:59:16 +0200 (Fri, 21 Dec 2012) $ #$Revision: 69808 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/23/62/2236239.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2236239 loop_ _publ_author_name 'Tiritiris, Ioannis' _publ_section_title ; Piperidine-1-carboximidamide ; _journal_coeditor_code GO2073 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3253 _journal_volume 68 _journal_year 2012 _chemical_formula_iupac 'C6 H13 N3' _chemical_formula_moiety 'C6 H13 N3' _chemical_formula_sum 'C6 H13 N3' _chemical_formula_weight 127.19 _chemical_melting_point 409 _chemical_name_systematic ; Piperidine-1-carboximidamide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 91.887(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.2193(9) _cell_length_b 5.5784(5) _cell_length_c 10.4885(7) _cell_measurement_reflns_used 4190 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 73.45 _cell_measurement_theta_min 3.62 _cell_volume 714.55(10) _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device_type 'Bruker Kappa APEXII DUO' _diffrn_measurement_method '\f scans, and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4190 _diffrn_reflns_theta_full 73.45 _diffrn_reflns_theta_max 73.45 _diffrn_reflns_theta_min 3.62 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.597 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_correction_T_min 0.830 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 280 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.193 _refine_diff_density_min -0.213 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 94 _refine_ls_number_reflns 1413 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0445 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0625P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1037 _refine_ls_wR_factor_ref 0.1122 _reflns_number_gt 1116 _reflns_number_total 1413 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL TIR29 IN P2(1)/C CELL 1.54178 12.21930 5.57840 10.48850 90.00000 91.88700 90.00000 ZERR 4 0.00090 0.00050 0.00070 0.00000 0.00400 0.00000 LATT 1 SYMM -X, Y+ 0.50000, -Z+ 0.50000 SFAC C H N UNIT 24 52 12 TEMP -173 L.S. 5 BOND $H CONF ACTA FMAP 2 PLAN 10 WGHT 0.062500 FVAR 1.19097 C1 1 0.385705 0.227183 0.207207 11.00000 0.02033 0.01671 = 0.02107 -0.00111 0.00041 0.00214 N1 3 0.419818 0.264759 0.325132 11.00000 0.02711 0.01867 = 0.02278 -0.00148 -0.00130 -0.00226 H11 2 0.466513 0.392516 0.325642 11.00000 0.03109 N2 3 0.408432 0.374321 0.107634 11.00000 0.03350 0.02111 = 0.01965 -0.00092 -0.00114 -0.00526 H21 2 0.404030 0.314837 0.024050 11.00000 0.03688 H22 2 0.459792 0.497211 0.125121 11.00000 0.03478 N3 3 0.324655 0.025288 0.179177 11.00000 0.02558 0.02025 = 0.02141 0.00013 -0.00361 -0.00323 C2 1 0.258896 -0.000670 0.061378 11.00000 0.03288 0.02612 = 0.02180 -0.00365 -0.00210 -0.00655 AFIX 23 H2A 2 0.259086 -0.170552 0.034081 11.00000 -1.20000 H2B 2 0.291451 0.096381 -0.006712 11.00000 -1.20000 AFIX 0 C3 1 0.141279 0.080722 0.080291 11.00000 0.03090 0.02736 = 0.02491 0.00172 -0.00914 -0.00160 AFIX 23 H3A 2 0.140341 0.254012 0.100591 11.00000 -1.20000 H3B 2 0.097203 0.055343 0.000541 11.00000 -1.20000 AFIX 0 C4 1 0.091505 -0.060227 0.188470 11.00000 0.02613 0.02680 = 0.02953 -0.00023 -0.00131 0.00089 AFIX 23 H4A 2 0.017870 0.004048 0.205381 11.00000 -1.20000 H4B 2 0.083255 -0.230362 0.163075 11.00000 -1.20000 AFIX 0 C5 1 0.163639 -0.043421 0.309061 11.00000 0.03131 0.02509 = 0.02540 0.00157 0.00119 -0.00218 AFIX 23 H5A 2 0.134082 -0.149313 0.375403 11.00000 -1.20000 H5B 2 0.162871 0.123129 0.341619 11.00000 -1.20000 AFIX 0 C6 1 0.281719 -0.117125 0.282890 11.00000 0.02921 0.01966 = 0.02468 0.00483 -0.00404 -0.00194 AFIX 23 H6A 2 0.328230 -0.093743 0.360974 11.00000 -1.20000 H6B 2 0.283732 -0.289184 0.259954 11.00000 -1.20000 HKLF 4 REM TIR29 IN P2(1)/C REM R1 = 0.0445 for 1116 Fo > 4sig(Fo) and 0.0588 for all 1413 data REM 94 parameters refined using 0 restraints END WGHT 0.0625 0.0000 REM Highest difference peak 0.193, deepest hole -0.213, 1-sigma level 0.048 Q1 1 0.3884 0.1796 0.4032 11.00000 0.05 0.19 Q2 1 0.3043 0.0261 -0.0205 11.00000 0.05 0.19 Q3 1 0.3227 0.3722 0.0466 11.00000 0.05 0.16 Q4 1 0.4465 0.2454 0.0357 11.00000 0.05 0.15 Q5 1 0.3670 0.2172 0.0124 11.00000 0.05 0.15 Q6 1 0.3804 0.3697 0.4001 11.00000 0.05 0.14 Q7 1 0.4246 0.1405 0.0108 11.00000 0.05 0.14 Q8 1 0.3366 0.5742 0.1213 11.00000 0.05 0.13 Q9 1 0.2554 -0.1651 0.0665 11.00000 0.05 0.13 Q10 1 0.0730 0.2119 0.0190 11.00000 0.05 0.13 ; _[local]_cod_data_source_file go2073.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2236239 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z loop_ _atom_site_type_symbol _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_symmetry_multiplicity C C1 0.38570(11) 0.2272(2) 0.20721(12) 0.0194(3) Uani d . 1 1 N N1 0.41982(10) 0.26476(18) 0.32513(11) 0.0229(3) Uani d . 1 1 H H11 0.4665(14) 0.393(3) 0.3256(16) 0.031(4) Uiso d . 1 1 N N2 0.40843(11) 0.37432(19) 0.10763(12) 0.0248(3) Uani d . 1 1 H H21 0.4040(14) 0.315(3) 0.0240(18) 0.037(4) Uiso d . 1 1 H H22 0.4598(14) 0.497(3) 0.1251(15) 0.035(4) Uiso d . 1 1 N N3 0.32466(10) 0.02529(17) 0.17918(10) 0.0225(3) Uani d . 1 1 C C2 0.25890(12) -0.0007(2) 0.06138(13) 0.0270(4) Uani d . 1 1 H H2A 0.2591 -0.1706 0.0341 0.032 Uiso calc R 1 1 H H2B 0.2915 0.0964 -0.0067 0.032 Uiso calc R 1 1 C C3 0.14128(12) 0.0807(2) 0.08029(14) 0.0279(4) Uani d . 1 1 H H3A 0.1403 0.2540 0.1006 0.034 Uiso calc R 1 1 H H3B 0.0972 0.0553 0.0005 0.034 Uiso calc R 1 1 C C4 0.09150(13) -0.0602(2) 0.18847(14) 0.0275(3) Uani d . 1 1 H H4A 0.0179 0.0040 0.2054 0.033 Uiso calc R 1 1 H H4B 0.0833 -0.2304 0.1631 0.033 Uiso calc R 1 1 C C5 0.16364(12) -0.0434(2) 0.30906(14) 0.0273(4) Uani d . 1 1 H H5A 0.1341 -0.1493 0.3754 0.033 Uiso calc R 1 1 H H5B 0.1629 0.1231 0.3416 0.033 Uiso calc R 1 1 C C6 0.28172(12) -0.1171(2) 0.28289(13) 0.0246(3) Uani d . 1 1 H H6A 0.3282 -0.0937 0.3610 0.030 Uiso calc R 1 1 H H6B 0.2837 -0.2892 0.2600 0.030 Uiso calc R 1 1 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 0.0203(7) 0.0167(6) 0.0211(7) 0.0021(4) 0.0004(5) -0.0011(4) N1 0.0271(7) 0.0187(5) 0.0228(6) -0.0023(4) -0.0013(5) -0.0015(4) N2 0.0335(7) 0.0211(5) 0.0196(6) -0.0053(5) -0.0011(5) -0.0009(4) N3 0.0256(7) 0.0203(5) 0.0214(6) -0.0032(4) -0.0036(5) 0.0001(4) C2 0.0329(9) 0.0261(6) 0.0218(7) -0.0065(5) -0.0021(6) -0.0037(5) C3 0.0309(9) 0.0274(6) 0.0249(8) -0.0016(6) -0.0091(6) 0.0017(5) C4 0.0261(8) 0.0268(7) 0.0295(8) 0.0009(5) -0.0013(6) -0.0002(5) C5 0.0313(9) 0.0251(6) 0.0254(8) -0.0022(5) 0.0012(6) 0.0016(5) C6 0.0292(8) 0.0197(6) 0.0247(7) -0.0019(5) -0.0040(6) 0.0048(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 C1 N2 124.09(11) N1 C1 N3 119.08(11) N2 C1 N3 116.82(12) C1 N1 H11 108.1(11) C1 N2 H21 119.8(10) C1 N2 H22 116.1(10) H21 N2 H22 117.2(14) C1 N3 C6 119.46(11) C1 N3 C2 122.78(10) C6 N3 C2 112.09(10) N3 C2 C3 110.80(11) N3 C2 H2A 109.5 C3 C2 H2A 109.5 N3 C2 H2B 109.5 C3 C2 H2B 109.5 H2A C2 H2B 108.1 C4 C3 C2 110.12(11) C4 C3 H3A 109.6 C2 C3 H3A 109.6 C4 C3 H3B 109.6 C2 C3 H3B 109.6 H3A C3 H3B 108.2 C5 C4 C3 110.67(12) C5 C4 H4A 109.5 C3 C4 H4A 109.5 C5 C4 H4B 109.5 C3 C4 H4B 109.5 H4A C4 H4B 108.1 C4 C5 C6 110.95(12) C4 C5 H5A 109.4 C6 C5 H5A 109.4 C4 C5 H5B 109.4 C6 C5 H5B 109.4 H5A C5 H5B 108.0 N3 C6 C5 110.55(11) N3 C6 H6A 109.5 C5 C6 H6A 109.5 N3 C6 H6B 109.5 C5 C6 H6B 109.5 H6A C6 H6B 108.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.3090(17) C1 N2 1.3640(17) C1 N3 1.3773(16) N1 H11 0.913(17) N2 H21 0.937(18) N2 H22 0.943(17) N3 C6 1.4585(17) N3 C2 1.4587(17) C2 C3 1.526(2) C2 H2A 0.9900 C2 H2B 0.9900 C3 C4 1.5235(19) C3 H3A 0.9900 C3 H3B 0.9900 C4 C5 1.521(2) C4 H4A 0.9900 C4 H4B 0.9900 C5 C6 1.534(2) C5 H5A 0.9900 C5 H5B 0.9900 C6 H6A 0.9900 C6 H6B 0.9900 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H21 N1 4_554 0.94(2) 2.15(2) 3.0710(10) 168.0(10) y N2 H22 N1 2_655 0.94(2) 2.15(2) 3.0900(10) 177.0(10) y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion N1 C1 N3 C6 11.63(18) N2 C1 N3 C6 -169.57(11) N1 C1 N3 C2 162.94(12) N2 C1 N3 C2 -18.25(18) C1 N3 C2 C3 -93.09(14) C6 N3 C2 C3 60.10(13) N3 C2 C3 C4 -56.89(14) C2 C3 C4 C5 53.91(15) C3 C4 C5 C6 -53.30(14) C1 N3 C6 C5 95.35(14) C2 N3 C6 C5 -58.83(14) C4 C5 C6 N3 55.17(13)