data_15srv065 _audit_creation_date 2015-03-13 _audit_creation_method ; Olex2 1.2-beta (compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998) ; _publ_contact_author_address ; Science site South Rd Durham ; _publ_contact_author_email d.s.yufit@durham.ac.uk _publ_contact_author_name 'Yufit, D.S.' _publ_contact_author_phone '' _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _chemical_name_common ? _chemical_name_systematic ; dimethyl (2-aminopropyl)fluoromalonate hydrochloride ; _chemical_formula_moiety 'Cl, C8 H15 F N O4' _chemical_formula_sum 'C8 H15 Cl F N O4' _chemical_formula_weight 243.66 _chemical_melting_point ? _chemical_oxdiff_formula 'C8 H15 Cl1 F1 N1 O4' 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' 'F' 'F' 0.0171 0.0103 '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' _space_group_crystal_system 'triclinic' _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 5.8210(4) _cell_length_b 6.4875(5) _cell_length_c 15.7485(12) _cell_angle_alpha 100.738(7) _cell_angle_beta 96.625(6) _cell_angle_gamma 94.612(6) _cell_volume 577.23(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3123 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 32.2490 _cell_measurement_theta_min 3.2000 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_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl1 Cl 0.75418(10) 1.29673(9) 0.51960(4) 0.02011(16) Uani 1 d . . . F1 F 0.6831(3) 0.9887(2) 0.17917(10) 0.0248(4) Uani 1 d . . . O1 O 0.5595(4) 0.7691(4) 0.01629(14) 0.0353(5) Uani 1 d . . . O2 O 0.1871(3) 0.7620(3) 0.04072(12) 0.0256(4) Uani 1 d . . . O3 O 0.3597(3) 0.5205(3) 0.19529(13) 0.0273(4) Uani 1 d . . . O4 O 0.7177(3) 0.6800(3) 0.24970(13) 0.0286(5) Uani 1 d . . . N1 N 0.2217(4) 1.1772(3) 0.44695(14) 0.0195(4) Uani 1 d . . . H1A H 0.2229 1.0478 0.4613 0.023 Uiso 1 calc . . GR H1B H 0.1086 1.2461 0.4719 0.023 Uiso 1 calc . . GR H1C H 0.3623 1.2530 0.4666 0.023 Uiso 1 calc . . GR C1 C 0.1745(5) 1.1523(4) 0.35047(17) 0.0227(5) Uani 1 d . . . H1D H 0.1831 1.2930 0.3345 0.027 Uiso 1 calc . . R H1E H 0.0157 1.0812 0.3295 0.027 Uiso 1 calc . . R C2 C 0.3501(4) 1.0233(4) 0.30724(17) 0.0203(5) Uani 1 d . . . H2A H 0.3518 0.8882 0.3278 0.024 Uiso 1 calc . . R H2B H 0.5072 1.1009 0.3242 0.024 Uiso 1 calc . . R C3 C 0.2916(5) 0.9785(4) 0.20797(17) 0.0206(5) Uani 1 d . . . H3A H 0.1380 0.8946 0.1910 0.025 Uiso 1 calc . . R H3B H 0.2815 1.1136 0.1878 0.025 Uiso 1 calc . . R C4 C 0.4737(4) 0.8589(4) 0.16362(17) 0.0188(5) Uani 1 d . . . C5 C 0.4151(5) 0.7910(4) 0.06354(17) 0.0215(5) Uani 1 d . . . C6 C 0.1074(6) 0.6948(5) -0.05202(18) 0.0320(7) Uani 1 d . . . H6A H 0.1722 0.7978 -0.0835 0.048 Uiso 1 calc . . GR H6B H -0.0628 0.6848 -0.0620 0.048 Uiso 1 calc . . GR H6C H 0.1590 0.5566 -0.0731 0.048 Uiso 1 calc . . GR C7 C 0.5104(4) 0.6631(4) 0.20300(16) 0.0196(5) Uani 1 d . . . C8 C 0.7546(7) 0.5106(5) 0.2970(2) 0.0450(9) Uani 1 d . . . H8A H 0.7465 0.3767 0.2554 0.068 Uiso 1 calc . . GR H8B H 0.6342 0.5019 0.3352 0.068 Uiso 1 calc . . GR H8C H 0.9080 0.5391 0.3322 0.068 Uiso 1 calc . . GR 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 Cl1 0.0160(3) 0.0143(3) 0.0302(3) 0.0050(2) 0.0028(2) 0.0012(2) F1 0.0211(8) 0.0210(8) 0.0318(9) 0.0086(6) 0.0015(6) -0.0064(6) O1 0.0295(11) 0.0484(13) 0.0288(11) 0.0056(10) 0.0077(9) 0.0071(10) O2 0.0227(10) 0.0319(10) 0.0215(10) 0.0081(8) 0.0000(7) -0.0038(8) O3 0.0314(11) 0.0161(9) 0.0331(11) 0.0079(8) -0.0020(8) -0.0038(8) O4 0.0290(11) 0.0172(9) 0.0372(11) 0.0071(8) -0.0089(9) 0.0037(8) N1 0.0172(10) 0.0139(9) 0.0272(11) 0.0020(8) 0.0043(8) 0.0029(8) C1 0.0219(13) 0.0192(12) 0.0263(13) 0.0025(10) 0.0004(10) 0.0060(10) C2 0.0214(13) 0.0167(11) 0.0229(13) 0.0038(10) 0.0017(10) 0.0053(10) C3 0.0229(13) 0.0159(11) 0.0232(13) 0.0048(10) 0.0007(10) 0.0047(10) C4 0.0165(12) 0.0139(11) 0.0255(13) 0.0064(10) 0.0005(10) -0.0027(9) C5 0.0259(14) 0.0159(11) 0.0235(13) 0.0066(10) 0.0022(10) 0.0016(10) C6 0.0348(16) 0.0369(16) 0.0216(14) 0.0082(12) -0.0037(12) -0.0075(13) C7 0.0221(13) 0.0162(11) 0.0203(12) 0.0026(9) 0.0023(10) 0.0035(10) C8 0.055(2) 0.0215(14) 0.053(2) 0.0121(14) -0.0272(17) 0.0069(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C4 1.394(3) . ? O1 C5 1.185(3) . ? O2 C5 1.323(3) . ? O2 C6 1.453(3) . ? O3 C7 1.202(3) . ? O4 C7 1.324(3) . ? O4 C8 1.454(3) . ? N1 H1A 0.9100 . ? N1 H1B 0.9100 . ? N1 H1C 0.9100 . ? N1 C1 1.488(3) . ? C1 H1D 0.9900 . ? C1 H1E 0.9900 . ? C1 C2 1.515(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.528(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.521(4) . ? C4 C5 1.545(4) . ? C4 C7 1.533(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 C5 O2 C6 116.1(2) . . ? C7 O4 C8 114.7(2) . . ? H1A N1 H1B 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? N1 C1 H1D 109.6 . . ? N1 C1 H1E 109.6 . . ? N1 C1 C2 110.3(2) . . ? H1D C1 H1E 108.1 . . ? C2 C1 H1D 109.6 . . ? C2 C1 H1E 109.6 . . ? C1 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C1 C2 C3 111.2(2) . . ? H2A C2 H2B 108.0 . . ? C3 C2 H2A 109.4 . . ? C3 C2 H2B 109.4 . . ? C2 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C4 C3 C2 111.7(2) . . ? C4 C3 H3A 109.3 . . ? C4 C3 H3B 109.3 . . ? F1 C4 C3 108.8(2) . . ? F1 C4 C5 106.4(2) . . ? F1 C4 C7 108.5(2) . . ? C3 C4 C5 114.6(2) . . ? C3 C4 C7 109.2(2) . . ? C7 C4 C5 109.1(2) . . ? O1 C5 O2 126.8(3) . . ? O1 C5 C4 122.9(3) . . ? O2 C5 C4 110.3(2) . . ? O2 C6 H6A 109.5 . . ? O2 C6 H6B 109.5 . . ? O2 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O3 C7 O4 125.8(2) . . ? O3 C7 C4 122.2(2) . . ? O4 C7 C4 111.8(2) . . ? O4 C8 H8A 109.5 . . ? O4 C8 H8B 109.5 . . ? O4 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 H1A Cl1 0.91 2.32 3.226(2) 172.2 2_676 N1 H1B Cl1 0.91 2.30 3.169(2) 158.9 1_455 N1 H1C Cl1 0.91 2.31 3.160(2) 154.7 . 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 F1 C4 C5 O1 31.3(3) . . . . ? F1 C4 C5 O2 -148.9(2) . . . . ? F1 C4 C7 O3 -176.5(2) . . . . ? F1 C4 C7 O4 7.7(3) . . . . ? N1 C1 C2 C3 174.8(2) . . . . ? C1 C2 C3 C4 177.0(2) . . . . ? C2 C3 C4 F1 -66.2(3) . . . . ? C2 C3 C4 C5 174.9(2) . . . . ? C2 C3 C4 C7 52.2(3) . . . . ? C3 C4 C5 O1 151.6(3) . . . . ? C3 C4 C5 O2 -28.6(3) . . . . ? C3 C4 C7 O3 65.0(3) . . . . ? C3 C4 C7 O4 -110.8(2) . . . . ? C5 C4 C7 O3 -60.9(3) . . . . ? C5 C4 C7 O4 123.2(2) . . . . ? C6 O2 C5 O1 0.5(4) . . . . ? C6 O2 C5 C4 -179.3(2) . . . . ? C7 C4 C5 O1 -85.7(3) . . . . ? C7 C4 C5 O2 94.1(2) . . . . ? C8 O4 C7 O3 -2.2(4) . . . . ? C8 O4 C7 C4 173.4(2) . . . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -1 0 1 0.1580 -1.0005 -0.0003 0.9997 -0.1132 -0.0550 -0.0020 1 0 -1 0.1580 1.0005 0.0003 -0.9997 0.1132 0.0550 0.0020 0 -1 0 0.0985 -0.0008 -0.9990 0.0010 -0.0046 -0.0026 0.1117 0 1 0 0.0985 0.0008 0.9990 -0.0010 0.0046 0.0026 -0.1117 0 0 1 0.0242 -0.0003 -0.0001 1.0009 -0.0290 0.0348 -0.0095 0 0 -1 0.0242 0.0003 0.0001 -1.0009 0.0290 -0.0348 0.0095 _olex2_submission_special_instructions 'No special instructions were received'