#------------------------------------------------------------------------------ #$Date: 2016-05-13 09:16:54 +0300 (Fri, 13 May 2016) $ #$Revision: 182930 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225231.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_7225231 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_absolute_configuration unk _chemical_formula_moiety 'C14 H17 N O3' _chemical_formula_sum 'C14 H17 N O3' _chemical_formula_weight 247.28 _space_group_crystal_system monoclinic _space_group_IT_number 7 _space_group_name_Hall 'P -2yc' _space_group_name_H-M_alt 'P 1 c 1' _symmetry_space_group_name_Hall 'P -2yc' _symmetry_space_group_name_H-M 'P 1 c 1' _atom_sites_solution_hydrogens geom _audit_creation_date 2016-01-15 _audit_creation_method ; Olex2 1.2 (compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103) ; _audit_update_record ; 2016-01-15 deposited with the CCDC. 2016-05-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.878(7) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.9545(5) _cell_length_b 10.6290(8) _cell_length_c 10.1521(6) _cell_measurement_reflns_used 1920 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.8270 _cell_measurement_theta_min 3.8350 _cell_volume 634.83(8) _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 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 16.2096 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; 1 omega -93.00 31.00 1.0000 5.6300 omega____ theta____ kappa____ phi______ frames - -22.4081 0.0000 -120.0000 124 2 omega -98.00 -68.00 1.0000 5.6300 omega____ theta____ kappa____ phi______ frames - -22.4081 -178.0000 0.0000 30 3 omega -81.00 -54.00 1.0000 5.6300 omega____ theta____ kappa____ phi______ frames - -22.4081 -178.0000 -180.0000 27 4 omega 8.00 65.00 1.0000 5.6300 omega____ theta____ kappa____ phi______ frames - 23.3456 -99.0000 -150.0000 57 5 omega -76.00 -26.00 1.0000 5.6300 omega____ theta____ kappa____ phi______ frames - -22.4081 119.0000 -135.0000 50 6 omega 4.00 77.00 1.0000 5.6300 omega____ theta____ kappa____ phi______ frames - 23.3456 57.0000 -150.0000 73 7 omega -2.00 93.00 1.0000 5.6300 omega____ theta____ kappa____ phi______ frames - 23.3456 0.0000 -150.0000 95 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0114048000 _diffrn_orient_matrix_UB_12 -0.0662222000 _diffrn_orient_matrix_UB_13 -0.0070568000 _diffrn_orient_matrix_UB_21 0.1000089000 _diffrn_orient_matrix_UB_22 -0.0020691000 _diffrn_orient_matrix_UB_23 -0.0298458000 _diffrn_orient_matrix_UB_31 0.0663442000 _diffrn_orient_matrix_UB_32 -0.0083271000 _diffrn_orient_matrix_UB_33 0.0636811000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_unetI/netI 0.0506 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5642 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.497 _diffrn_reflns_theta_min 2.792 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.81220 _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 colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.294 _exptl_crystal_description prism _exptl_crystal_F_000 264 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.318 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.052 _refine_ls_abs_structure_details ; Refined as a perfect inversion twin. ; _refine_ls_abs_structure_Flack 0.5 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 166 _refine_ls_number_reflns 2768 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.073 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0442 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0635P)^2^+0.0015P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1090 _refine_ls_wR_factor_ref 0.1147 _reflns_Friedel_coverage 0.992 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 2542 _reflns_number_total 2768 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ra10249b2.cif _cod_data_source_block dvd76c _cod_original_cell_volume 634.84(8) _cod_database_code 7225231 _chemical_oxdiff_formula 'C10 H13 N' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _reflns_odcompleteness_completeness 99.88 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 28.51 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C1(H1), C2(H2) 2.b Secondary CH2 refined with riding coordinates: C3(H3A,H3B), C5(H5A,H5B) 2.c Aromatic/amide H refined with riding coordinates: C9(H9), C10(H10), C12(H12), C13(H13) 2.d Idealised Me refined as rotating group: C6(H6A,H6B,H6C), C14(H14A,H14B,H14C) 2.e Idealised tetrahedral OH refined as rotating group: O3(H3) ; _shelx_shelxl_version_number 2014/7 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn O1 O -0.3879(4) 0.31058(19) 0.42534(19) 0.0207(4) Uani 1 1 d . O2 O 0.0889(4) 0.59221(19) 0.7726(2) 0.0235(5) Uani 1 1 d . O3 O 0.4365(4) 0.5396(2) 0.7313(2) 0.0249(5) Uani 1 1 d . H3 H 0.4783 0.5878 0.7933 0.037 Uiso 1 1 calc GR N1 N -0.0331(4) 0.2602(2) 0.5323(2) 0.0177(5) Uani 1 1 d . C1 C 0.1814(4) 0.3183(2) 0.5942(3) 0.0170(6) Uani 1 1 d . H1 H 0.2989 0.2988 0.5395 0.020 Uiso 1 1 calc R C2 C 0.1263(5) 0.4629(3) 0.5814(3) 0.0171(6) Uani 1 1 d . H2 H 0.2010 0.4963 0.5093 0.021 Uiso 1 1 calc R C3 C -0.1314(5) 0.4722(3) 0.5366(3) 0.0192(6) Uani 1 1 d . H3A H -0.2080 0.4973 0.6101 0.023 Uiso 1 1 calc R H3B H -0.1667 0.5325 0.4647 0.023 Uiso 1 1 calc R C4 C -0.2004(5) 0.3416(3) 0.4901(3) 0.0178(6) Uani 1 1 d . C5 C -0.0433(5) 0.1279(3) 0.4942(3) 0.0224(6) Uani 1 1 d . H5A H -0.2010 0.1030 0.4704 0.027 Uiso 1 1 calc R H5B H 0.0231 0.0774 0.5699 0.027 Uiso 1 1 calc R C6 C 0.0821(6) 0.1016(3) 0.3771(3) 0.0260(7) Uani 1 1 d . H6A H 0.0232 0.1551 0.3037 0.039 Uiso 1 1 calc GR H6B H 0.0607 0.0152 0.3508 0.039 Uiso 1 1 calc GR H6C H 0.2413 0.1180 0.4032 0.039 Uiso 1 1 calc GR C7 C 0.2102(5) 0.5381(3) 0.7060(3) 0.0177(6) Uani 1 1 d . C8 C 0.2578(5) 0.2680(3) 0.7339(3) 0.0173(6) Uani 1 1 d . C9 C 0.4738(5) 0.2152(3) 0.7659(3) 0.0199(6) Uani 1 1 d . H9 H 0.5680 0.2100 0.7011 0.024 Uiso 1 1 calc R C10 C 0.5502(5) 0.1704(3) 0.8939(3) 0.0230(6) Uani 1 1 d . H10 H 0.6945 0.1351 0.9130 0.028 Uiso 1 1 calc R C11 C 0.4145(5) 0.1773(3) 0.9936(3) 0.0217(6) Uani 1 1 d . C12 C 0.1976(5) 0.2298(3) 0.9611(3) 0.0205(6) Uani 1 1 d . H12 H 0.1036 0.2354 1.0260 0.025 Uiso 1 1 calc R C13 C 0.1204(5) 0.2741(3) 0.8327(3) 0.0193(6) Uani 1 1 d . H13 H -0.0248 0.3080 0.8130 0.023 Uiso 1 1 calc R C14 C 0.4972(6) 0.1278(3) 1.1317(3) 0.0307(7) Uani 1 1 d . H14A H 0.6492 0.0962 1.1359 0.046 Uiso 1 1 calc GR H14B H 0.3991 0.0611 1.1518 0.046 Uiso 1 1 calc GR H14C H 0.4959 0.1945 1.1954 0.046 Uiso 1 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 O1 0.0121(10) 0.0297(10) 0.0185(9) 0.0017(8) -0.0030(7) -0.0011(8) O2 0.0191(11) 0.0303(11) 0.0208(9) -0.0041(8) 0.0020(9) 0.0018(9) O3 0.0145(10) 0.0339(12) 0.0251(10) -0.0079(8) -0.0011(8) -0.0019(9) N1 0.0109(11) 0.0225(11) 0.0189(11) 0.0009(9) -0.0001(9) -0.0011(9) C1 0.0100(13) 0.0232(14) 0.0171(12) -0.0022(10) 0.0001(10) -0.0005(11) C2 0.0105(13) 0.0233(13) 0.0167(11) 0.0008(10) -0.0006(10) -0.0004(11) C3 0.0123(14) 0.0250(14) 0.0194(13) -0.0017(10) -0.0002(11) 0.0017(10) C4 0.0114(13) 0.0296(15) 0.0128(11) 0.0023(10) 0.0036(10) 0.0006(11) C5 0.0172(14) 0.0244(14) 0.0234(13) 0.0004(10) -0.0032(11) -0.0019(11) C6 0.0256(17) 0.0242(13) 0.0269(14) -0.0046(11) -0.0001(13) 0.0032(12) C7 0.0150(14) 0.0210(13) 0.0159(12) 0.0017(10) -0.0011(10) -0.0015(11) C8 0.0129(14) 0.0192(13) 0.0188(13) -0.0004(10) -0.0004(11) -0.0009(10) C9 0.0126(14) 0.0251(14) 0.0220(13) 0.0003(11) 0.0030(11) 0.0011(11) C10 0.0136(14) 0.0298(15) 0.0240(15) 0.0031(12) -0.0023(11) 0.0015(12) C11 0.0220(16) 0.0192(13) 0.0219(13) -0.0006(10) -0.0031(12) -0.0027(11) C12 0.0211(14) 0.0238(14) 0.0169(12) -0.0010(10) 0.0041(11) -0.0016(12) C13 0.0142(14) 0.0206(14) 0.0229(12) -0.0008(10) 0.0019(11) 0.0000(11) C14 0.0331(19) 0.0342(17) 0.0221(14) 0.0033(12) -0.0046(13) 0.0048(15) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C7 O3 H3 109.5 C4 N1 C1 114.8(2) C4 N1 C5 122.7(2) C5 N1 C1 121.1(2) N1 C1 H1 108.5 N1 C1 C2 102.6(2) N1 C1 C8 111.5(2) C2 C1 H1 108.5 C8 C1 H1 108.5 C8 C1 C2 116.7(2) C1 C2 H2 107.6 C3 C2 C1 105.9(2) C3 C2 H2 107.6 C7 C2 C1 114.2(2) C7 C2 H2 107.6 C7 C2 C3 113.5(2) C2 C3 H3A 110.9 C2 C3 H3B 110.9 H3A C3 H3B 108.9 C4 C3 C2 104.2(2) C4 C3 H3A 110.9 C4 C3 H3B 110.9 O1 C4 N1 123.9(3) O1 C4 C3 126.0(3) N1 C4 C3 110.0(2) N1 C5 H5A 109.2 N1 C5 H5B 109.2 N1 C5 C6 112.2(2) H5A C5 H5B 107.9 C6 C5 H5A 109.2 C6 C5 H5B 109.2 C5 C6 H6A 109.5 C5 C6 H6B 109.5 C5 C6 H6C 109.5 H6A C6 H6B 109.5 H6A C6 H6C 109.5 H6B C6 H6C 109.5 O2 C7 O3 124.1(2) O2 C7 C2 124.7(3) O3 C7 C2 111.1(2) C9 C8 C1 119.5(2) C13 C8 C1 122.2(3) C13 C8 C9 118.4(2) C8 C9 H9 119.6 C10 C9 C8 120.8(3) C10 C9 H9 119.6 C9 C10 H10 119.4 C11 C10 C9 121.2(3) C11 C10 H10 119.4 C10 C11 C12 117.9(3) C10 C11 C14 121.0(3) C12 C11 C14 121.1(3) C11 C12 H12 119.5 C13 C12 C11 120.9(3) C13 C12 H12 119.5 C8 C13 C12 120.8(3) C8 C13 H13 119.6 C12 C13 H13 119.6 C11 C14 H14A 109.5 C11 C14 H14B 109.5 C11 C14 H14C 109.5 H14A C14 H14B 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C4 1.249(3) O2 C7 1.208(4) O3 H3 0.8200 O3 C7 1.332(3) N1 C1 1.470(3) N1 C4 1.339(4) N1 C5 1.457(4) C1 H1 0.9800 C1 C2 1.572(4) C1 C8 1.518(4) C2 H2 0.9800 C2 C3 1.535(4) C2 C7 1.515(4) C3 H3A 0.9700 C3 H3B 0.9700 C3 C4 1.503(4) C5 H5A 0.9700 C5 H5B 0.9700 C5 C6 1.524(4) C6 H6A 0.9600 C6 H6B 0.9600 C6 H6C 0.9600 C8 C9 1.395(4) C8 C13 1.390(4) C9 H9 0.9300 C9 C10 1.393(4) C10 H10 0.9300 C10 C11 1.391(4) C11 C12 1.399(4) C11 C14 1.507(4) C12 H12 0.9300 C12 C13 1.395(4) C13 H13 0.9300 C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600