#------------------------------------------------------------------------------ #$Date: 2016-05-13 09:16:54 +0300 (Fri, 13 May 2016) $ #$Revision: 182930 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225225.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7225225 loop_ _publ_author_name 'Dar'in, Dmitry' 'Bakulina, Olga' 'Nikolskaya, Sofia' 'Gluzdikov, Ivan' 'Krasavin, Mikhail' _publ_section_title ; The rare cis-configured trisubstituted lactam products obtained by the Castagnoli-Cushman reaction in N,N-dimethylformamide ; _journal_name_full 'RSC Adv.' _journal_paper_doi 10.1039/C6RA10249B _journal_year 2016 _chemical_formula_moiety 'C14 H16 F N O3' _chemical_formula_sum 'C14 H16 F N O3' _chemical_formula_weight 265.28 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2015-12-14 _audit_creation_method ; Olex2 1.2-ac2 (compiled 2012.03.27 svn.r2268, GUI svn.r4156) ; _audit_update_record ; 2015-12-14 deposited with the CCDC. 2016-05-11 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 92.142(11) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.9465(16) _cell_length_b 15.9223(18) _cell_length_c 8.4185(7) _cell_measurement_reflns_used 1539 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.3750 _cell_measurement_theta_min 3.5210 _cell_volume 1332.3(3) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 16.2096 _diffrn_measured_fraction_theta_full 0.9783 _diffrn_measured_fraction_theta_max 0.9783 _diffrn_measurement_details ; 1 omega 2.00 95.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ frames - 23.4968 38.0000 -150.0000 93 2 omega 20.00 64.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ frames - 23.4968 -99.0000 30.0000 44 3 omega 39.00 68.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ frames - 23.4968 178.0000 60.0000 29 4 omega -47.00 28.00 1.0000 23.0000 omega____ theta____ kappa____ phi______ frames - 23.4968 -77.0000 -90.0000 75 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0520354000 _diffrn_orient_matrix_UB_12 -0.0037319000 _diffrn_orient_matrix_UB_13 -0.0547970000 _diffrn_orient_matrix_UB_21 0.0479973000 _diffrn_orient_matrix_UB_22 -0.0048914000 _diffrn_orient_matrix_UB_23 0.0637695000 _diffrn_orient_matrix_UB_31 -0.0096950000 _diffrn_orient_matrix_UB_32 -0.0441748000 _diffrn_orient_matrix_UB_33 -0.0022631000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_unetI/netI 0.0411 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 6163 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 3.28 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.81886 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.304 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 3007 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0418 _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^)+(0.0429P)^2^+0.3867P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0947 _refine_ls_wR_factor_ref 0.1077 _reflns_number_gt 2327 _reflns_number_total 3007 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c6ra10249b2.cif _cod_data_source_block dvd-73 _cod_database_code 7225225 _chemical_oxdiff_formula 'O3 C12 H20' _reflns_odcompleteness_completeness 97.83 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 28.51 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' 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags F1 F 1.16613(9) 0.67426(7) 0.43887(11) 0.0327(3) Uani 1 1 d . O1 O 0.44291(11) 0.46031(6) 0.69834(12) 0.0223(3) Uani 1 1 d . N1 N 0.62725(12) 0.54644(7) 0.73128(14) 0.0172(3) Uani 1 1 d . O3 O 0.59174(12) 0.81851(7) 0.64063(14) 0.0281(3) Uani 1 1 d . H3 H 0.5702 0.8634 0.6802 0.042 Uiso 1 1 calc R C3 C 0.42995(15) 0.60911(9) 0.63231(18) 0.0194(3) Uani 1 1 d . H3A H 0.3646 0.6277 0.7075 0.023 Uiso 1 1 calc R H3B H 0.3843 0.6002 0.5298 0.023 Uiso 1 1 calc R C8 C 0.50499(15) 0.75938(9) 0.68036(17) 0.0189(3) Uani 1 1 d . C13 C 0.95063(16) 0.61314(10) 0.43341(18) 0.0241(3) Uani 1 1 d . H13 H 0.9695 0.5850 0.3400 0.029 Uiso 1 1 calc R O2 O 0.40949(12) 0.77279(7) 0.76129(15) 0.0323(3) Uani 1 1 d . C4 C 0.49841(15) 0.52982(9) 0.68953(16) 0.0177(3) Uani 1 1 d . C14 C 0.82656(15) 0.60432(10) 0.50158(18) 0.0211(3) Uani 1 1 d . H14 H 0.7610 0.5702 0.4533 0.025 Uiso 1 1 calc R C5 C 0.71938(15) 0.48368(9) 0.80075(17) 0.0202(3) Uani 1 1 d . H5A H 0.8043 0.4867 0.7480 0.024 Uiso 1 1 calc R H5B H 0.6820 0.4282 0.7817 0.024 Uiso 1 1 calc R C12 C 1.04530(15) 0.66462(10) 0.50763(18) 0.0231(3) Uani 1 1 d . C1 C 0.66487(14) 0.63571(9) 0.71781(16) 0.0169(3) Uani 1 1 d . H1 H 0.6689 0.6611 0.8239 0.020 Uiso 1 1 calc R C2 C 0.54252(14) 0.67349(9) 0.61911(16) 0.0170(3) Uani 1 1 d . H2 H 0.5664 0.6783 0.5076 0.020 Uiso 1 1 calc R C10 C 0.89843(15) 0.69700(10) 0.71423(18) 0.0219(3) Uani 1 1 d . H10 H 0.8812 0.7244 0.8089 0.026 Uiso 1 1 calc R C11 C 1.02291(16) 0.70713(10) 0.64593(19) 0.0250(4) Uani 1 1 d . H11 H 1.0887 0.7416 0.6926 0.030 Uiso 1 1 calc R C7 C 0.8394(2) 0.42782(12) 1.0467(2) 0.0377(4) Uani 1 1 d . H7A H 0.8557 0.4377 1.1582 0.056 Uiso 1 1 calc R H7B H 0.9231 0.4296 0.9935 0.056 Uiso 1 1 calc R H7C H 0.7986 0.3736 1.0315 0.056 Uiso 1 1 calc R C9 C 0.79963(14) 0.64641(9) 0.64249(17) 0.0180(3) Uani 1 1 d . C6 C 0.74527(19) 0.49546(11) 0.97798(19) 0.0317(4) Uani 1 1 d . H6A H 0.6605 0.4933 1.0312 0.038 Uiso 1 1 calc R H6B H 0.7849 0.5503 0.9975 0.038 Uiso 1 1 calc 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 F1 0.0183(5) 0.0474(6) 0.0328(5) 0.0100(5) 0.0053(4) 0.0013(4) O1 0.0269(6) 0.0175(6) 0.0227(5) -0.0005(4) 0.0020(4) -0.0025(4) N1 0.0212(6) 0.0144(6) 0.0161(6) 0.0001(5) 0.0013(5) 0.0010(5) O3 0.0358(7) 0.0148(5) 0.0348(7) -0.0039(5) 0.0138(5) -0.0020(5) C3 0.0201(7) 0.0171(7) 0.0210(7) -0.0008(6) -0.0004(6) 0.0007(6) C8 0.0234(8) 0.0173(7) 0.0158(6) 0.0011(6) -0.0002(6) 0.0013(6) C13 0.0249(8) 0.0274(9) 0.0203(7) 0.0013(6) 0.0044(6) 0.0050(6) O2 0.0324(7) 0.0238(6) 0.0419(7) -0.0077(5) 0.0177(5) -0.0003(5) C4 0.0238(8) 0.0175(7) 0.0120(6) -0.0017(5) 0.0039(5) 0.0000(6) C14 0.0217(8) 0.0213(8) 0.0204(7) -0.0012(6) 0.0013(6) -0.0006(6) C5 0.0232(8) 0.0174(7) 0.0200(7) 0.0023(6) 0.0012(6) 0.0028(6) C12 0.0153(7) 0.0293(9) 0.0250(8) 0.0110(7) 0.0027(6) 0.0031(6) C1 0.0216(7) 0.0156(7) 0.0136(7) -0.0015(5) 0.0019(5) 0.0009(6) C2 0.0202(7) 0.0165(7) 0.0143(6) 0.0000(6) 0.0015(5) 0.0014(6) C10 0.0257(8) 0.0216(8) 0.0185(7) 0.0001(6) -0.0008(6) -0.0006(6) C11 0.0218(8) 0.0280(9) 0.0248(8) 0.0055(7) -0.0038(6) -0.0053(6) C7 0.0444(11) 0.0393(11) 0.0287(9) 0.0088(8) -0.0055(8) 0.0100(9) C9 0.0206(7) 0.0162(7) 0.0171(7) 0.0037(6) -0.0006(6) 0.0019(6) C6 0.0439(11) 0.0320(10) 0.0191(8) 0.0023(7) -0.0012(7) 0.0126(8) 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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C4 N1 C5 123.19(12) C4 N1 C1 114.35(12) C5 N1 C1 122.14(12) C8 O3 H3 109.5 H3A C3 H3B 108.8 C4 C3 H3A 110.7 C4 C3 H3B 110.7 C4 C3 C2 105.22(12) C2 C3 H3A 110.7 C2 C3 H3B 110.7 O3 C8 C2 112.58(12) O2 C8 O3 123.26(14) O2 C8 C2 124.11(14) C14 C13 H13 120.8 C12 C13 H13 120.8 C12 C13 C14 118.37(14) O1 C4 N1 125.66(14) O1 C4 C3 124.79(14) N1 C4 C3 109.54(12) C13 C14 H14 119.9 C13 C14 C9 120.29(14) C9 C14 H14 119.9 N1 C5 H5A 109.0 N1 C5 H5B 109.0 N1 C5 C6 112.94(12) H5A C5 H5B 107.8 C6 C5 H5A 109.0 C6 C5 H5B 109.0 F1 C12 C13 118.19(14) F1 C12 C11 118.61(14) C11 C12 C13 123.20(14) N1 C1 H1 109.2 N1 C1 C2 102.49(11) N1 C1 C9 111.83(11) C2 C1 H1 109.2 C9 C1 H1 109.2 C9 C1 C2 114.63(11) C3 C2 C1 105.13(11) C3 C2 H2 109.1 C8 C2 C3 113.05(12) C8 C2 C1 111.26(11) C8 C2 H2 109.1 C1 C2 H2 109.1 C11 C10 H10 119.6 C9 C10 H10 119.6 C9 C10 C11 120.79(14) C12 C11 C10 117.89(14) C12 C11 H11 121.1 C10 C11 H11 121.1 H7A C7 H7B 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 C6 C7 H7A 109.5 C6 C7 H7B 109.5 C6 C7 H7C 109.5 C14 C9 C1 120.17(13) C10 C9 C14 119.45(14) C10 C9 C1 120.37(13) C5 C6 C7 111.39(14) C5 C6 H6A 109.4 C5 C6 H6B 109.4 C7 C6 H6A 109.4 C7 C6 H6B 109.4 H6A C6 H6B 108.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C12 1.3621(17) O1 C4 1.2402(18) N1 C4 1.3425(19) N1 C5 1.4630(18) N1 C1 1.4752(18) O3 H3 0.8200 O3 C8 1.3283(18) C3 H3A 0.9700 C3 H3B 0.9700 C3 C4 1.505(2) C3 C2 1.525(2) C8 O2 1.2085(18) C8 C2 1.513(2) C13 H13 0.9300 C13 C14 1.387(2) C13 C12 1.380(2) C14 H14 0.9300 C14 C9 1.397(2) C5 H5A 0.9700 C5 H5B 0.9700 C5 C6 1.516(2) C12 C11 1.372(2) C1 H1 0.9800 C1 C2 1.5677(19) C1 C9 1.514(2) C2 H2 0.9800 C10 H10 0.9300 C10 C11 1.394(2) C10 C9 1.391(2) C11 H11 0.9300 C7 H7A 0.9600 C7 H7B 0.9600 C7 H7C 0.9600 C7 C6 1.527(2) C6 H6A 0.9700 C6 H6B 0.9700