#------------------------------------------------------------------------------ #$Date: 2016-05-13 09:16:54 +0300 (Fri, 13 May 2016) $ #$Revision: 182930 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225226.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_7225226 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 'C16 H21 N O4' _chemical_formula_sum 'C16 H21 N O4' _chemical_formula_weight 291.34 _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 100.374(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.4049(2) _cell_length_b 21.3010(6) _cell_length_c 10.8631(3) _cell_measurement_reflns_used 8007 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 31.8240 _cell_measurement_theta_min 3.3270 _cell_volume 1457.83(7) _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 0.9991 _diffrn_measured_fraction_theta_max 0.9991 _diffrn_measurement_details ; 1 omega -102.00 -42.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -25.4031 178.0000 -120.0000 60 2 omega 4.00 72.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.4968 38.0000 -90.0000 68 3 omega 28.00 69.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.4968 -108.0000 162.0000 41 4 omega -25.00 68.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.4968 -99.0000 -90.0000 93 5 omega -4.00 64.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.4968 77.0000 150.0000 68 6 omega -3.00 88.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.4968 77.0000 -90.0000 91 7 omega -4.00 97.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.4968 77.0000 30.0000 101 8 omega -16.00 99.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.4968 0.0000 -150.0000 115 9 omega -25.00 68.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.4968 -99.0000 90.0000 93 10 omega -44.00 70.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 26.4968 -19.0000 90.0000 114 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0514484000 _diffrn_orient_matrix_UB_12 -0.0276806000 _diffrn_orient_matrix_UB_13 -0.0152881000 _diffrn_orient_matrix_UB_21 -0.0416929000 _diffrn_orient_matrix_UB_22 -0.0167377000 _diffrn_orient_matrix_UB_23 0.0465776000 _diffrn_orient_matrix_UB_31 -0.0910838000 _diffrn_orient_matrix_UB_32 -0.0079437000 _diffrn_orient_matrix_UB_33 -0.0446937000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_unetI/netI 0.0240 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 23949 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.70 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.68126 _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 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.456 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.064 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 194 _refine_ls_number_reflns 3349 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0464 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0732P)^2^+0.7915P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1248 _refine_ls_wR_factor_ref 0.1302 _reflns_number_gt 2959 _reflns_number_total 3349 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c6ra10249b2.cif _cod_data_source_block dvd-34 _cod_original_cell_volume 1457.85(8) _cod_database_code 7225226 _chemical_oxdiff_formula 'O3 C12 H20' _reflns_odcompleteness_completeness 99.91 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.01 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 O3 O 0.28271(16) 0.28962(5) 0.46178(9) 0.0188(2) Uani 1 1 d . H3 H 0.2104 0.3076 0.4022 0.028 Uiso 1 1 calc R O1 O 1.02178(16) 0.14631(5) 0.80065(9) 0.0176(2) Uani 1 1 d . O2 O 0.53492(17) 0.29685(5) 0.34377(10) 0.0233(3) Uani 1 1 d . N1 N 0.73092(17) 0.14760(5) 0.64815(10) 0.0120(2) Uani 1 1 d . C1 C 0.5851(2) 0.17836(6) 0.54538(12) 0.0120(3) Uani 1 1 d . H1 H 0.4408 0.1712 0.5606 0.014 Uiso 1 1 calc R C10 C 0.5975(2) 0.14876(6) 0.41895(12) 0.0135(3) Uani 1 1 d . O4 O 0.59565(19) 0.06797(5) 0.06796(10) 0.0245(3) Uani 1 1 d . C2 C 0.6217(2) 0.25023(6) 0.54919(12) 0.0126(3) Uani 1 1 d . H2 H 0.5839 0.2663 0.6268 0.015 Uiso 1 1 calc R C9 C 0.4778(2) 0.28184(6) 0.43982(13) 0.0140(3) Uani 1 1 d . C5 C 0.9099(2) 0.17413(6) 0.71066(12) 0.0134(3) Uani 1 1 d . C4 C 0.9791(2) 0.23834(7) 0.67353(13) 0.0159(3) Uani 1 1 d . H4A H 1.1277 0.2361 0.6665 0.019 Uiso 1 1 calc R H4B H 0.9673 0.2676 0.7403 0.019 Uiso 1 1 calc R C11 C 0.7862(2) 0.12630(6) 0.38906(13) 0.0160(3) Uani 1 1 d . H11 H 0.9106 0.1293 0.4481 0.019 Uiso 1 1 calc R C12 C 0.7937(2) 0.09932(7) 0.27252(13) 0.0180(3) Uani 1 1 d . H12 H 0.9215 0.0846 0.2544 0.022 Uiso 1 1 calc R C3 C 0.8550(2) 0.26456(6) 0.55170(13) 0.0147(3) Uani 1 1 d . H3A H 0.8766 0.3095 0.5476 0.018 Uiso 1 1 calc R H3B H 0.9021 0.2451 0.4807 0.018 Uiso 1 1 calc R C6 C 0.6725(2) 0.08529(6) 0.69455(13) 0.0159(3) Uani 1 1 d . H6 H 0.7155 0.0858 0.7858 0.019 Uiso 1 1 calc R C15 C 0.4132(2) 0.14414(6) 0.32777(13) 0.0162(3) Uani 1 1 d . H15 H 0.2854 0.1590 0.3455 0.019 Uiso 1 1 calc R C13 C 0.6081(2) 0.09468(6) 0.18387(13) 0.0181(3) Uani 1 1 d . C14 C 0.4177(2) 0.11774(7) 0.21134(13) 0.0188(3) Uani 1 1 d . H14 H 0.2940 0.1154 0.1518 0.023 Uiso 1 1 calc R C8 C 0.7976(3) 0.03272(7) 0.64550(16) 0.0247(3) Uani 1 1 d . H8A H 0.7552 0.0295 0.5564 0.037 Uiso 1 1 calc R H8B H 0.7697 -0.0063 0.6837 0.037 Uiso 1 1 calc R H8C H 0.9466 0.0419 0.6656 0.037 Uiso 1 1 calc R C16 C 0.7807(3) 0.03617(8) 0.04254(15) 0.0271(3) Uani 1 1 d . H16A H 0.7459 0.0140 -0.0354 0.041 Uiso 1 1 calc R H16B H 0.8297 0.0069 0.1086 0.041 Uiso 1 1 calc R H16C H 0.8903 0.0663 0.0375 0.041 Uiso 1 1 calc R C7 C 0.4346(2) 0.07223(7) 0.66683(15) 0.0206(3) Uani 1 1 d . H7A H 0.3611 0.1048 0.7029 0.031 Uiso 1 1 calc R H7B H 0.4067 0.0325 0.7022 0.031 Uiso 1 1 calc R H7C H 0.3861 0.0712 0.5779 0.031 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 O3 0.0146(5) 0.0244(6) 0.0170(5) 0.0044(4) 0.0014(4) 0.0029(4) O1 0.0170(5) 0.0159(5) 0.0183(5) 0.0006(4) -0.0013(4) 0.0001(4) O2 0.0241(6) 0.0251(6) 0.0224(5) 0.0093(4) 0.0087(4) 0.0063(4) N1 0.0131(5) 0.0088(5) 0.0138(5) 0.0011(4) 0.0016(4) -0.0005(4) C1 0.0112(6) 0.0103(6) 0.0143(6) 0.0008(5) 0.0013(5) -0.0003(4) C10 0.0169(6) 0.0080(6) 0.0152(6) 0.0005(5) 0.0019(5) -0.0015(5) O4 0.0336(6) 0.0234(6) 0.0155(5) -0.0053(4) 0.0019(4) -0.0009(5) C2 0.0142(6) 0.0091(6) 0.0147(6) 0.0000(4) 0.0028(5) 0.0001(4) C9 0.0155(6) 0.0090(6) 0.0172(6) -0.0005(5) 0.0025(5) -0.0002(5) C5 0.0135(6) 0.0126(6) 0.0144(6) -0.0026(5) 0.0030(5) 0.0005(5) C4 0.0139(6) 0.0136(6) 0.0193(7) -0.0011(5) 0.0006(5) -0.0025(5) C11 0.0172(6) 0.0127(6) 0.0175(7) -0.0005(5) 0.0013(5) -0.0011(5) C12 0.0219(7) 0.0133(6) 0.0197(7) -0.0007(5) 0.0058(5) 0.0004(5) C3 0.0155(6) 0.0100(6) 0.0186(7) 0.0002(5) 0.0038(5) -0.0020(5) C6 0.0191(7) 0.0094(6) 0.0185(7) 0.0030(5) 0.0014(5) -0.0018(5) C15 0.0165(6) 0.0116(6) 0.0198(7) 0.0025(5) 0.0010(5) -0.0012(5) C13 0.0289(8) 0.0100(6) 0.0154(7) 0.0007(5) 0.0039(6) -0.0033(5) C14 0.0230(7) 0.0138(7) 0.0171(7) 0.0026(5) -0.0030(5) -0.0041(5) C8 0.0272(8) 0.0108(6) 0.0362(9) 0.0028(6) 0.0063(6) 0.0022(6) C16 0.0373(9) 0.0240(8) 0.0213(7) -0.0056(6) 0.0090(6) 0.0010(7) C7 0.0208(7) 0.0138(7) 0.0270(8) 0.0036(5) 0.0041(6) -0.0045(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' O O 0.0106 0.0060 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 N1 C6 119.23(10) C5 N1 C1 124.12(11) C5 N1 C6 116.47(11) N1 C1 C10 111.69(10) N1 C1 C2 110.32(10) C10 C1 C2 113.61(11) C11 C10 C1 122.68(12) C11 C10 C15 117.87(12) C15 C10 C1 119.45(12) C13 O4 C16 117.34(12) C9 C2 C1 110.43(10) C3 C2 C1 110.02(10) C3 C2 C9 112.33(11) O3 C9 C2 111.90(11) O2 C9 O3 124.36(13) O2 C9 C2 123.72(12) O1 C5 N1 120.69(12) O1 C5 C4 118.79(12) N1 C5 C4 120.52(12) C5 C4 C3 115.52(11) C10 C11 C12 121.65(13) C13 C12 C11 119.44(13) C2 C3 C4 107.44(11) N1 C6 C8 110.80(12) N1 C6 C7 113.48(11) C7 C6 C8 111.45(12) C14 C15 C10 121.28(13) O4 C13 C12 124.50(14) O4 C13 C14 115.70(13) C12 C13 C14 119.80(13) C15 C14 C13 119.94(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O3 C9 1.3238(17) O1 C5 1.2522(17) O2 C9 1.2094(17) N1 C1 1.4738(16) N1 C5 1.3470(17) N1 C6 1.4912(16) C1 C10 1.5263(18) C1 C2 1.5481(18) C10 C11 1.3918(19) C10 C15 1.4010(19) O4 C13 1.3709(17) O4 C16 1.434(2) C2 C9 1.5232(18) C2 C3 1.5205(18) C5 C4 1.5146(19) C4 C3 1.5219(19) C11 C12 1.3989(19) C12 C13 1.392(2) C6 C8 1.528(2) C6 C7 1.5246(19) C15 C14 1.389(2) C13 C14 1.396(2)