#------------------------------------------------------------------------------ #$Date: 2019-11-23 18:53:56 +0200 (Sat, 23 Nov 2019) $ #$Revision: 234529 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/63/4036309.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_4036309 loop_ _publ_author_name 'Chaiyaveij, Duangduan' 'Batsanov, Andrei S.' 'Fox, Mark A.' 'Marder, Todd B.' 'Whiting, Andrew' _publ_section_title ; An Experimental and Computational Approach to Understanding the Reactions of Acyl Nitroso Compounds in [4 + 2] Cycloadditions. ; _journal_issue 19 _journal_name_full 'The Journal of organic chemistry' _journal_page_first 9518 _journal_page_last 9534 _journal_paper_doi 10.1021/acs.joc.5b01470 _journal_volume 80 _journal_year 2015 _chemical_formula_moiety 'C13 H16 N2 O2' _chemical_formula_sum 'C13 H16 N2 O2' _chemical_formula_weight 232.28 _chemical_melting_point 374 _chemical_name_systematic ; 4,5-Dimethyl-N-phenyl-3,6-dihydro-2H-1,2-oxazine-2-carbox-amide ; _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2012-03-01 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 13.5078(8) _cell_length_b 9.1660(5) _cell_length_c 19.8312(13) _cell_measurement_reflns_used 9141 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.999 _cell_measurement_theta_min 2.548 _cell_volume 2455.4(3) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _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 ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_unetI/netI 0.0183 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 27298 _diffrn_reflns_theta_full 30.01 _diffrn_reflns_theta_max 30.01 _diffrn_reflns_theta_min 2.05 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_correction_T_min 0.6333 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2009/1 (Bruker) was used for absorption correction. R(int) was 0.0896 before and 0.0500 after correction. The Ratio of minimum to maximum transmission is 0.8489. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 992 _exptl_crystal_size_max 0.85 _exptl_crystal_size_mid 0.8 _exptl_crystal_size_min 0.4 _refine_diff_density_max 0.337 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.048 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 161 _refine_ls_number_reflns 3576 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0426 _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^)+(0.0707P)^2^+0.6475P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1151 _refine_ls_wR_factor_ref 0.1258 _reflns_number_gt 2937 _reflns_number_total 3576 _reflns_threshold_expression I>2\s(I) _cod_data_source_file jo5b01470_si_002.cif _cod_data_source_block 25 _cod_database_code 4036309 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 '-x, y+1/2, -z+1/2' 4 'x+1/2, -y+1/2, -z' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 'x, -y-1/2, z-1/2' 8 '-x-1/2, y-1/2, z' 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.64558(6) 0.40016(8) 0.44651(4) 0.02745(18) Uani 1 1 d . . . O2 O 0.66406(5) 0.04583(8) 0.38126(4) 0.02636(17) Uani 1 1 d . . . N1 N 0.63841(6) 0.24719(9) 0.44501(4) 0.02502(19) Uani 1 1 d . . . N2 N 0.74516(6) 0.25877(10) 0.35421(4) 0.02417(18) Uani 1 1 d . . . H2N H 0.7563(11) 0.3428(16) 0.3671(7) 0.029(3) Uiso 1 1 d . . . C1 C 0.68127(7) 0.17589(10) 0.39109(5) 0.02180(19) Uani 1 1 d . . . C2 C 0.56837(8) 0.46339(11) 0.40566(6) 0.0291(2) Uani 1 1 d . . . H2A H 0.5847 0.4483 0.3575 0.035 Uiso 1 1 calc R . . H2B H 0.5662 0.5699 0.4139 0.035 Uiso 1 1 calc R . . C3 C 0.46807(8) 0.40003(12) 0.41955(5) 0.0298(2) Uani 1 1 d . . . C4 C 0.45816(8) 0.27723(13) 0.45449(5) 0.0291(2) Uani 1 1 d . . . C5 C 0.54846(8) 0.19357(12) 0.47645(5) 0.0283(2) Uani 1 1 d . . . H5A H 0.5552 0.2008 0.5261 0.034 Uiso 1 1 calc R . . H5B H 0.5397 0.0893 0.4649 0.034 Uiso 1 1 calc R . . C6 C 0.36133(9) 0.20706(17) 0.47336(7) 0.0432(3) Uani 1 1 d . . . H6A H 0.3081 0.2795 0.4704 0.064(3) Uiso 1 1 d R . . H6B H 0.3654 0.1698 0.5196 0.064(3) Uiso 1 1 d R . . H6C H 0.3474 0.1263 0.4424 0.064(3) Uiso 1 1 d R . . C7 C 0.38412(10) 0.48448(18) 0.38882(7) 0.0456(3) Uani 1 1 d . . . H7A1 H 0.3772 0.4575 0.3412 0.049(4) Uiso 0.50 1 d PR A 1 H7A2 H 0.3978 0.5892 0.3923 0.049(4) Uiso 0.50 1 d PR A 1 H7A3 H 0.3226 0.4618 0.4128 0.049(4) Uiso 0.50 1 d PR A 1 H7B1 H 0.3488 0.5539 0.4178 0.049(4) Uiso 0.50 1 d PR A 2 H7B2 H 0.3987 0.5375 0.3471 0.049(4) Uiso 0.50 1 d PR A 2 H7B3 H 0.3321 0.4197 0.3718 0.049(4) Uiso 0.50 1 d PR A 2 C8 C 0.80691(7) 0.20319(11) 0.30262(5) 0.0234(2) Uani 1 1 d . . . C9 C 0.90038(8) 0.26659(11) 0.29495(6) 0.0285(2) Uani 1 1 d . . . H9 H 0.9199 0.3447 0.3235 0.034 Uiso 1 1 calc R . . C10 C 0.96468(8) 0.21548(12) 0.24564(6) 0.0336(2) Uani 1 1 d . . . H10 H 1.0280 0.2591 0.2405 0.040 Uiso 1 1 calc R . . C11 C 0.93701(9) 0.10137(13) 0.20392(6) 0.0348(3) Uani 1 1 d . . . H11 H 0.9814 0.0656 0.1707 0.042 Uiso 1 1 calc R . . C12 C 0.84377(9) 0.03985(13) 0.21113(6) 0.0339(2) Uani 1 1 d . . . H12 H 0.8246 -0.0384 0.1825 0.041 Uiso 1 1 calc R . . C13 C 0.77781(8) 0.09113(12) 0.25970(5) 0.0283(2) Uani 1 1 d . . . H13 H 0.7135 0.0499 0.2635 0.034 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 O1 0.0277(4) 0.0227(4) 0.0319(4) -0.0037(3) 0.0024(3) -0.0024(3) O2 0.0248(4) 0.0203(3) 0.0340(4) 0.0012(3) 0.0017(3) 0.0000(3) N1 0.0231(4) 0.0223(4) 0.0296(4) 0.0005(3) 0.0037(3) -0.0008(3) N2 0.0228(4) 0.0207(4) 0.0290(4) -0.0019(3) 0.0043(3) -0.0015(3) C1 0.0183(4) 0.0225(4) 0.0246(4) 0.0014(3) -0.0014(3) 0.0020(3) C2 0.0345(5) 0.0243(5) 0.0284(5) 0.0006(4) 0.0063(4) 0.0047(4) C3 0.0277(5) 0.0367(6) 0.0249(5) -0.0025(4) 0.0021(4) 0.0079(4) C4 0.0227(5) 0.0381(6) 0.0265(5) -0.0025(4) 0.0052(4) 0.0006(4) C5 0.0270(5) 0.0293(5) 0.0287(5) 0.0042(4) 0.0071(4) -0.0002(4) C6 0.0268(6) 0.0588(8) 0.0439(7) -0.0008(6) 0.0104(5) -0.0055(5) C7 0.0388(7) 0.0595(8) 0.0385(7) 0.0049(6) -0.0009(5) 0.0203(6) C8 0.0218(4) 0.0227(4) 0.0257(4) 0.0034(3) 0.0021(3) 0.0041(3) C9 0.0249(5) 0.0241(5) 0.0365(5) 0.0017(4) 0.0053(4) -0.0005(4) C10 0.0275(5) 0.0312(5) 0.0419(6) 0.0069(5) 0.0111(4) 0.0033(4) C11 0.0360(6) 0.0365(6) 0.0319(5) 0.0038(4) 0.0098(4) 0.0112(5) C12 0.0374(6) 0.0359(6) 0.0285(5) -0.0046(4) 0.0009(4) 0.0062(5) C13 0.0258(5) 0.0318(5) 0.0272(5) -0.0010(4) -0.0005(4) 0.0020(4) 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 N1 O1 C2 109.83(8) O1 N1 C5 112.73(8) C1 N1 O1 117.37(8) C1 N1 C5 121.57(9) C1 N2 H2N 118.1(10) C1 N2 C8 124.11(8) C8 N2 H2N 116.8(10) O2 C1 N1 120.15(9) O2 C1 N2 125.10(9) N2 C1 N1 114.67(8) O1 C2 H2A 108.9 O1 C2 H2B 108.9 O1 C2 C3 113.23(9) H2A C2 H2B 107.7 C3 C2 H2A 108.9 C3 C2 H2B 108.9 C2 C3 C7 114.07(10) C4 C3 C2 120.99(10) C4 C3 C7 124.90(11) C3 C4 C5 120.06(9) C3 C4 C6 125.40(11) C6 C4 C5 114.50(10) N1 C5 C4 112.43(9) N1 C5 H5A 109.1 N1 C5 H5B 109.1 C4 C5 H5A 109.1 C4 C5 H5B 109.1 H5A C5 H5B 107.8 C4 C6 H6A 109.4 C4 C6 H6B 109.4 C4 C6 H6C 109.5 H6A C6 H6B 109.5 H6A C6 H6C 109.5 H6B C6 H6C 109.5 C3 C7 H7A1 109.5 C3 C7 H7A2 109.5 C3 C7 H7A3 109.5 C3 C7 H7B1 117.6 C3 C7 H7B2 116.5 C3 C7 H7B3 111.6 H7A1 C7 H7A2 109.5 H7A1 C7 H7A3 109.5 H7A2 C7 H7A3 109.5 H7B1 C7 H7B2 105.7 H7B1 C7 H7B3 104.3 H7B2 C7 H7B3 98.9 C9 C8 N2 117.48(9) C13 C8 N2 122.80(9) C13 C8 C9 119.71(9) C8 C9 H9 120.0 C10 C9 C8 120.07(10) C10 C9 H9 120.0 C9 C10 H10 119.8 C11 C10 C9 120.42(11) C11 C10 H10 119.8 C10 C11 H11 120.3 C10 C11 C12 119.37(10) C12 C11 H11 120.3 C11 C12 H12 119.5 C11 C12 C13 120.96(11) C13 C12 H12 119.5 C8 C13 C12 119.43(10) C8 C13 H13 120.3 C12 C13 H13 120.3 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 N1 1.4057(11) O1 C2 1.4421(14) O2 C1 1.2301(12) N1 C1 1.3805(13) N1 C5 1.4515(13) N2 H2N 0.825(15) N2 C1 1.3626(13) N2 C8 1.4150(13) C2 H2A 0.9900 C2 H2B 0.9900 C2 C3 1.4997(16) C3 C4 1.3285(16) C3 C7 1.5022(16) C4 C5 1.5051(15) C4 C6 1.5048(16) C5 H5A 0.9900 C5 H5B 0.9900 C6 H6A 0.9801 C6 H6B 0.9803 C6 H6C 0.9797 C7 H7A1 0.9801 C7 H7A2 0.9800 C7 H7A3 0.9801 C7 H7B1 0.9800 C7 H7B2 0.9801 C7 H7B3 0.9800 C8 C9 1.3981(14) C8 C13 1.3907(14) C9 H9 0.9500 C9 C10 1.3892(15) C10 H10 0.9500 C10 C11 1.3851(18) C11 H11 0.9500 C11 C12 1.3873(18) C12 H12 0.9500 C12 C13 1.3937(15) C13 H13 0.9500 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 N2 H2N O2 0.825(15) 2.168(15) 2.9520(11) 158.8(13) 8_765