#------------------------------------------------------------------------------ #$Date: 2016-05-13 09:16:54 +0300 (Fri, 13 May 2016) $ #$Revision: 182930 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225229.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_7225229 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 'C17 H23 N O4' _chemical_formula_sum 'C17 H23 N O4' _chemical_formula_weight 305.36 _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 iterative _atom_sites_solution_secondary difmap _audit_creation_date 2015-12-16 _audit_creation_method ; Olex2 1.2-ac2 (compiled 2012.03.27 svn.r2268, GUI svn.r4156) ; _audit_update_record ; 2015-12-16 deposited with the CCDC. 2016-05-11 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 105.054(12) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.5824(9) _cell_length_b 21.392(2) _cell_length_c 11.5002(13) _cell_measurement_reflns_used 2342 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.0860 _cell_measurement_theta_min 3.3120 _cell_volume 1563.8(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 'J. Appl. Cryst. (2007) 40, 786-790' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 16.2096 _diffrn_measured_fraction_theta_full 0.9670 _diffrn_measured_fraction_theta_max 0.9670 _diffrn_measurement_details ; 1 omega -1.00 48.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -20.4081 57.0000 -90.0000 49 2 omega -40.00 42.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -20.4081 57.0000 0.0000 82 3 omega -14.00 21.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -20.4081 -99.0000 -90.0000 35 4 omega -25.00 61.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 21.5018 -99.0000 -120.0000 86 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0153861000 _diffrn_orient_matrix_UB_12 -0.0038454000 _diffrn_orient_matrix_UB_13 -0.0584449000 _diffrn_orient_matrix_UB_21 -0.0328131000 _diffrn_orient_matrix_UB_22 -0.0315899000 _diffrn_orient_matrix_UB_23 -0.0004008000 _diffrn_orient_matrix_UB_31 -0.1055646000 _diffrn_orient_matrix_UB_32 0.0091471000 _diffrn_orient_matrix_UB_33 -0.0259481000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_unetI/netI 0.0535 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 7643 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 3.20 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.64899 _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 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.750 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.075 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 204 _refine_ls_number_reflns 3480 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.102 _refine_ls_R_factor_all 0.0915 _refine_ls_R_factor_gt 0.0767 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+2.2421P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1865 _refine_ls_wR_factor_ref 0.1980 _reflns_number_gt 2843 _reflns_number_total 3480 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c6ra10249b2.cif _cod_data_source_block dvd35 _cod_database_code 7225229 _chemical_oxdiff_formula 'O3 C20 H18' _reflns_odcompleteness_completeness 96.70 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 27.50 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 O4 O 0.4456(3) 0.20134(9) 0.35200(17) 0.0222(4) Uani 1 1 d . H4 H 0.3382 0.1868 0.3072 0.033 Uiso 1 1 calc R O1 O 1.1109(3) 0.35289(8) 0.72248(17) 0.0211(4) Uani 1 1 d . O2 O 0.5585(3) 0.41866(9) 0.06272(17) 0.0246(5) Uani 1 1 d . O3 O 0.2176(3) 0.24517(10) 0.44219(18) 0.0271(5) Uani 1 1 d . N1 N 0.7618(3) 0.35554(10) 0.62783(19) 0.0167(5) Uani 1 1 d . C14 C 0.5526(4) 0.39792(12) 0.1743(2) 0.0193(5) Uani 1 1 d . C12 C 0.7606(4) 0.36566(12) 0.3705(2) 0.0195(5) Uani 1 1 d . H12 H 0.8917 0.3584 0.4233 0.023 Uiso 1 1 calc R C15 C 0.3694(4) 0.38744(12) 0.2110(2) 0.0206(6) Uani 1 1 d . H15 H 0.2383 0.3945 0.1582 0.025 Uiso 1 1 calc R C5 C 0.9497(4) 0.32542(12) 0.6627(2) 0.0174(5) Uani 1 1 d . C7 C 0.7407(4) 0.42193(12) 0.6713(2) 0.0195(5) Uani 1 1 d . C11 C 0.5785(4) 0.35473(11) 0.4088(2) 0.0169(5) Uani 1 1 d . C13 C 0.7488(4) 0.38727(13) 0.2549(2) 0.0211(6) Uani 1 1 d . H13 H 0.8714 0.3947 0.2312 0.025 Uiso 1 1 calc R C6 C 0.3962(4) 0.23389(12) 0.4387(2) 0.0188(5) Uani 1 1 d . C1 C 0.5846(4) 0.32883(12) 0.5337(2) 0.0171(5) Uani 1 1 d . H1 H 0.4545 0.3423 0.5526 0.021 Uiso 1 1 calc R C2 C 0.5864(4) 0.25653(12) 0.5364(2) 0.0172(5) Uani 1 1 d . H2 H 0.5647 0.2437 0.6141 0.021 Uiso 1 1 calc R C3 C 0.7986(4) 0.23113(12) 0.5303(2) 0.0185(5) Uani 1 1 d . H3A H 0.8293 0.2441 0.4559 0.022 Uiso 1 1 calc R H3B H 0.7977 0.1858 0.5329 0.022 Uiso 1 1 calc R C16 C 0.3846(4) 0.36624(12) 0.3277(2) 0.0196(5) Uani 1 1 d . H16 H 0.2621 0.3596 0.3519 0.023 Uiso 1 1 calc R C10 C 0.5106(4) 0.44397(12) 0.6310(3) 0.0220(6) Uani 1 1 d . H10A H 0.4637 0.4432 0.5447 0.033 Uiso 1 1 calc R H10B H 0.5005 0.4858 0.6591 0.033 Uiso 1 1 calc R H10C H 0.4241 0.4167 0.6640 0.033 Uiso 1 1 calc R C4 C 0.9644(4) 0.25673(12) 0.6378(2) 0.0188(5) Uani 1 1 d . H4A H 0.9554 0.2337 0.7089 0.023 Uiso 1 1 calc R H4B H 1.1020 0.2485 0.6251 0.023 Uiso 1 1 calc R C9 C 0.8786(4) 0.46697(13) 0.6213(3) 0.0233(6) Uani 1 1 d . H9A H 1.0229 0.4540 0.6477 0.035 Uiso 1 1 calc R H9B H 0.8646 0.5085 0.6499 0.035 Uiso 1 1 calc R H9C H 0.8346 0.4666 0.5349 0.035 Uiso 1 1 calc R C17 C 0.3597(5) 0.42992(14) -0.0215(2) 0.0253(6) Uani 1 1 d . H17A H 0.3818 0.4418 -0.0977 0.038 Uiso 1 1 calc R H17B H 0.2876 0.4629 0.0080 0.038 Uiso 1 1 calc R H17C H 0.2762 0.3925 -0.0312 0.038 Uiso 1 1 calc R C8 C 0.8023(5) 0.42190(14) 0.8101(2) 0.0255(6) Uani 1 1 d . H8A H 0.7158 0.3926 0.8385 0.038 Uiso 1 1 calc R H8B H 0.7820 0.4630 0.8388 0.038 Uiso 1 1 calc R H8C H 0.9474 0.4101 0.8394 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 O4 0.0161(10) 0.0290(10) 0.0189(10) -0.0054(7) -0.0002(8) -0.0019(7) O1 0.0166(10) 0.0261(9) 0.0172(9) 0.0010(7) -0.0016(7) -0.0010(7) O2 0.0222(11) 0.0385(11) 0.0118(9) 0.0041(8) 0.0020(8) 0.0015(8) O3 0.0129(10) 0.0477(12) 0.0203(10) -0.0079(8) 0.0039(8) -0.0055(8) N1 0.0121(11) 0.0237(11) 0.0126(10) -0.0011(8) 0.0003(8) -0.0015(8) C14 0.0225(14) 0.0243(12) 0.0099(12) -0.0001(9) 0.0019(10) -0.0001(10) C12 0.0125(13) 0.0299(13) 0.0136(12) -0.0003(9) -0.0013(10) 0.0001(10) C15 0.0163(13) 0.0260(13) 0.0171(13) -0.0001(10) -0.0001(10) 0.0017(10) C5 0.0138(13) 0.0275(13) 0.0093(11) 0.0025(9) -0.0001(9) -0.0002(10) C7 0.0178(13) 0.0229(12) 0.0164(12) -0.0005(9) 0.0015(10) 0.0000(10) C11 0.0138(13) 0.0225(12) 0.0126(12) -0.0018(9) 0.0002(10) -0.0006(9) C13 0.0148(13) 0.0317(14) 0.0166(13) -0.0005(10) 0.0040(10) -0.0019(10) C6 0.0190(14) 0.0245(12) 0.0127(12) 0.0006(9) 0.0037(10) -0.0050(10) C1 0.0116(12) 0.0270(13) 0.0117(12) -0.0006(9) 0.0012(9) -0.0009(9) C2 0.0131(13) 0.0271(13) 0.0100(11) -0.0010(9) 0.0003(9) -0.0014(10) C3 0.0162(13) 0.0240(12) 0.0141(12) -0.0012(9) 0.0018(10) -0.0003(10) C16 0.0120(13) 0.0281(13) 0.0179(13) -0.0006(10) 0.0027(10) -0.0002(10) C10 0.0164(13) 0.0253(13) 0.0231(14) -0.0020(10) 0.0028(11) 0.0004(10) C4 0.0124(13) 0.0268(13) 0.0155(12) 0.0007(9) 0.0005(10) 0.0009(9) C9 0.0183(14) 0.0250(13) 0.0259(15) 0.0012(10) 0.0045(11) -0.0012(10) C17 0.0250(15) 0.0346(15) 0.0129(12) 0.0007(10) -0.0011(11) 0.0052(11) C8 0.0250(15) 0.0321(14) 0.0164(13) -0.0034(10) 0.0000(11) 0.0028(11) 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 C14 O2 C17 116.5(2) C5 N1 C7 119.9(2) C5 N1 C1 121.0(2) C1 N1 C7 118.5(2) O2 C14 C15 125.0(2) O2 C14 C13 115.4(2) C15 C14 C13 119.6(2) C13 C12 C11 121.1(2) C16 C15 C14 119.5(2) O1 C5 N1 121.1(2) O1 C5 C4 118.4(2) N1 C5 C4 120.4(2) N1 C7 C10 110.7(2) N1 C7 C9 110.4(2) N1 C7 C8 108.5(2) C10 C7 C8 106.6(2) C9 C7 C10 109.1(2) C9 C7 C8 111.5(2) C12 C11 C1 122.7(2) C16 C11 C12 118.1(2) C16 C11 C1 119.2(2) C12 C13 C14 120.1(2) O4 C6 C2 114.0(2) O3 C6 O4 124.0(2) O3 C6 C2 122.0(2) N1 C1 C11 111.7(2) N1 C1 C2 111.7(2) C11 C1 C2 112.3(2) C6 C2 C1 107.6(2) C3 C2 C6 116.1(2) C3 C2 C1 111.1(2) C2 C3 C4 108.0(2) C11 C16 C15 121.7(2) C5 C4 C3 115.9(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O4 C6 1.324(3) O1 C5 1.251(3) O2 C14 1.368(3) O2 C17 1.432(3) O3 C6 1.211(3) N1 C5 1.359(3) N1 C7 1.524(3) N1 C1 1.484(3) C14 C15 1.395(4) C14 C13 1.399(4) C12 C11 1.400(4) C12 C13 1.390(4) C15 C16 1.395(4) C5 C4 1.505(4) C7 C10 1.538(4) C7 C9 1.535(4) C7 C8 1.541(4) C11 C1 1.531(3) C11 C16 1.393(4) C6 C2 1.528(3) C1 C2 1.547(3) C2 C3 1.517(4) C3 C4 1.522(3)