data_14srv004 _audit_creation_date 2014-04-04 _audit_creation_method ; Olex2 1.2-beta (compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816) ; _publ_contact_author_address ; Durham University Chemistry Science site South Rd Durham DH1 3LE UK ; _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 ; ? ; _chemical_formula_moiety 'Cl, C7 H13 F N O4' _chemical_formula_sum 'C7 H13 Cl F N O4' _chemical_formula_weight 229.63 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 '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' _space_group_crystal_system 'monoclinic' _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 12.2350(7) _cell_length_b 11.3068(7) _cell_length_c 7.6415(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.2891(17) _cell_angle_gamma 90.00 _cell_volume 1040.12(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9971 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 31.54 _cell_measurement_theta_min 2.47 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 0.501476(19) 0.85721(2) 0.20873(3) 0.01750(9) Uani 1 d . . . F1 F 0.82834(5) 0.67909(5) 0.01818(8) 0.01878(14) Uani 1 d . . . O1 O 0.87659(6) 0.39998(7) 0.21097(11) 0.02117(17) Uani 1 d . . . O2 O 0.99028(7) 0.55145(7) 0.18471(12) 0.02671(19) Uani 1 d . . . O3 O 0.75641(6) 0.39687(7) -0.15572(9) 0.01785(16) Uani 1 d . . . O4 O 0.77481(6) 0.57242(7) -0.28658(10) 0.01928(16) Uani 1 d . . . N1 N 0.60238(9) 0.61344(9) 0.35824(13) 0.02004(19) Uani 1 d . . . C1 C 0.80051(8) 0.56142(8) 0.03289(12) 0.01301(18) Uani 1 d . . . C2 C 0.69467(8) 0.55431(9) 0.11183(12) 0.01387(18) Uani 1 d . . . C3 C 0.71079(9) 0.60942(10) 0.29601(13) 0.0188(2) Uani 1 d . . . C4 C 0.90168(8) 0.50422(9) 0.15045(12) 0.01393(18) Uani 1 d . . . C5 C 0.96777(10) 0.33852(11) 0.32313(18) 0.0257(2) Uani 1 d . . . C6 C 0.77742(8) 0.51151(9) -0.15736(13) 0.01372(18) Uani 1 d . . . C7 C 0.72684(11) 0.34234(11) -0.32981(16) 0.0251(2) Uani 1 d . . . H1A H 0.6123(13) 0.6254(14) 0.477(2) 0.030(4) Uiso 1 d . . . H1B H 0.5657(13) 0.5449(14) 0.333(2) 0.026(4) Uiso 1 d . . . H1C H 0.5637(14) 0.6708(15) 0.309(2) 0.032(4) Uiso 1 d . . . H2A H 0.6726(11) 0.4728(12) 0.1148(17) 0.016(3) Uiso 1 d . . . H2B H 0.6366(11) 0.5959(13) 0.0339(18) 0.017(3) Uiso 1 d . . . H3A H 0.7387(12) 0.6874(14) 0.2945(19) 0.024(4) Uiso 1 d . . . H3B H 0.7635(12) 0.5633(13) 0.3807(19) 0.021(3) Uiso 1 d . . . H5A H 0.9390(13) 0.2630(15) 0.351(2) 0.032(4) Uiso 1 d . . . H5B H 0.9948(16) 0.3867(17) 0.427(2) 0.047(5) Uiso 1 d . . . H5C H 1.0238(17) 0.3250(18) 0.263(3) 0.048(5) Uiso 1 d . . . H7A H 0.6624(14) 0.3808(14) -0.397(2) 0.030(4) Uiso 1 d . . . H7B H 0.7068(14) 0.2623(15) -0.308(2) 0.033(4) Uiso 1 d . . . H7C H 0.7868(15) 0.3470(14) -0.390(2) 0.032(4) Uiso 1 d . . . 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 0.01823(13) 0.01942(14) 0.01470(13) 0.00247(8) 0.00256(9) 0.00198(8) F1 0.0233(3) 0.0114(3) 0.0204(3) 0.0033(2) 0.0003(2) -0.0027(2) O1 0.0160(3) 0.0167(4) 0.0280(4) 0.0093(3) -0.0036(3) -0.0009(3) O2 0.0159(4) 0.0208(4) 0.0401(5) 0.0061(3) -0.0041(3) -0.0038(3) O3 0.0223(4) 0.0166(3) 0.0138(3) -0.0025(3) 0.0009(3) -0.0011(3) O4 0.0193(4) 0.0244(4) 0.0140(3) 0.0045(3) 0.0028(3) 0.0017(3) N1 0.0291(5) 0.0159(4) 0.0172(4) -0.0002(3) 0.0096(4) 0.0031(4) C1 0.0150(4) 0.0106(4) 0.0128(4) 0.0015(3) 0.0005(3) -0.0010(3) C2 0.0154(4) 0.0151(4) 0.0108(4) -0.0006(3) 0.0013(3) 0.0009(3) C3 0.0223(5) 0.0204(5) 0.0132(4) -0.0033(4) 0.0022(4) -0.0005(4) C4 0.0150(4) 0.0136(4) 0.0129(4) 0.0000(3) 0.0015(3) 0.0005(3) C5 0.0214(5) 0.0201(5) 0.0319(6) 0.0097(5) -0.0055(5) 0.0037(4) C6 0.0105(4) 0.0170(4) 0.0135(4) 0.0001(3) 0.0017(3) 0.0013(3) C7 0.0301(6) 0.0257(6) 0.0177(5) -0.0077(4) -0.0005(4) -0.0001(4) _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 C1 1.3829(11) . ? O1 C4 1.3222(12) . ? O1 C5 1.4562(13) . ? O2 C4 1.1948(12) . ? O3 C6 1.3219(12) . ? O3 C7 1.4522(13) . ? O4 C6 1.1996(12) . ? N1 C3 1.4877(14) . ? N1 H1A 0.907(17) . ? N1 H1B 0.899(16) . ? N1 H1C 0.850(18) . ? C1 C2 1.5252(13) . ? C1 C4 1.5362(13) . ? C1 C6 1.5379(13) . ? C2 C3 1.5194(13) . ? C2 H2A 0.961(14) . ? C2 H2B 0.964(14) . ? C3 H3A 0.946(16) . ? C3 H3B 0.979(15) . ? C5 H5A 0.963(16) . ? C5 H5B 0.972(19) . ? C5 H5C 0.91(2) . ? C7 H7A 0.963(17) . ? C7 H7B 0.961(17) . ? C7 H7C 0.935(18) . ? 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 C4 O1 C5 115.46(8) . . ? C6 O3 C7 115.13(8) . . ? C3 N1 H1A 111.0(10) . . ? C3 N1 H1B 110.3(10) . . ? C3 N1 H1C 109.8(11) . . ? H1A N1 H1B 108.2(14) . . ? H1A N1 H1C 107.3(15) . . ? H1B N1 H1C 110.2(14) . . ? F1 C1 C2 108.76(8) . . ? F1 C1 C4 105.56(7) . . ? F1 C1 C6 106.41(7) . . ? C2 C1 C4 113.51(8) . . ? C2 C1 C6 109.20(7) . . ? C4 C1 C6 113.02(8) . . ? C1 C2 H2A 108.7(8) . . ? C1 C2 H2B 108.3(8) . . ? C3 C2 C1 111.46(8) . . ? C3 C2 H2A 111.2(8) . . ? C3 C2 H2B 109.4(8) . . ? H2A C2 H2B 107.6(11) . . ? N1 C3 C2 109.45(9) . . ? N1 C3 H3A 108.6(9) . . ? N1 C3 H3B 109.0(9) . . ? C2 C3 H3A 111.0(9) . . ? C2 C3 H3B 110.8(8) . . ? H3A C3 H3B 107.9(12) . . ? O1 C4 C1 111.51(8) . . ? O2 C4 O1 125.46(9) . . ? O2 C4 C1 123.01(9) . . ? O1 C5 H5A 106.4(10) . . ? O1 C5 H5B 109.1(11) . . ? O1 C5 H5C 110.5(12) . . ? H5A C5 H5B 113.6(14) . . ? H5A C5 H5C 107.7(16) . . ? H5B C5 H5C 109.5(17) . . ? O3 C6 C1 110.73(8) . . ? O4 C6 O3 126.45(9) . . ? O4 C6 C1 122.74(9) . . ? O3 C7 H7A 109.9(10) . . ? O3 C7 H7B 105.5(10) . . ? O3 C7 H7C 109.8(10) . . ? H7A C7 H7B 108.0(14) . . ? H7A C7 H7C 110.6(14) . . ? H7B C7 H7C 112.8(14) . . ? 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 0.907(17) 2.421(17) 3.1605(9) 138.9(13) 4_576 N1 H1A O4 0.907(17) 2.506(16) 3.1602(13) 129.3(13) 1_556 N1 H1B Cl1 0.899(16) 2.278(16) 3.1682(10) 170.8(13) 2_645 N1 H1C Cl1 0.850(18) 2.324(18) 3.1499(10) 164.0(15) . 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 C1 C2 C3 -60.80(10) . . . . ? F1 C1 C4 O1 164.51(8) . . . . ? F1 C1 C4 O2 -13.61(13) . . . . ? F1 C1 C6 O3 176.27(7) . . . . ? F1 C1 C6 O4 -6.73(12) . . . . ? C1 C2 C3 N1 173.26(8) . . . . ? C2 C1 C4 O1 45.49(11) . . . . ? C2 C1 C4 O2 -132.63(10) . . . . ? C2 C1 C6 O3 -66.50(10) . . . . ? C2 C1 C6 O4 110.50(10) . . . . ? C4 C1 C2 C3 56.37(11) . . . . ? C4 C1 C6 O3 60.87(10) . . . . ? C4 C1 C6 O4 -122.13(10) . . . . ? C5 O1 C4 O2 -2.31(16) . . . . ? C5 O1 C4 C1 179.63(9) . . . . ? C6 C1 C2 C3 -176.53(8) . . . . ? C6 C1 C4 O1 -79.59(10) . . . . ? C6 C1 C4 O2 102.30(11) . . . . ? C7 O3 C6 O4 -0.41(14) . . . . ? C7 O3 C6 C1 176.45(9) . . . . ?