#------------------------------------------------------------------------------ #$Date: 2014-07-15 22:48:18 +0300 (Tue, 15 Jul 2014) $ #$Revision: 120443 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/17/7151726.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_7151726 loop_ _publ_author_name 'Franklin, Andrew I.' 'Bensa, David' 'Adams, Harry' 'Coldham, Iain' _publ_section_title ; Transannular dipolar cycloaddition as an approach towards the synthesis of the core ring system of the sarain alkaloids. ; _journal_issue 6 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 1901 _journal_page_last 1907 _journal_volume 9 _journal_year 2011 _chemical_absolute_configuration unk _chemical_formula_moiety 'C8 H13 N O3' _chemical_formula_sum 'C8 H13 N O3' _chemical_formula_weight 171.19 _chemical_name_systematic ; ? ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 103.144(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 6.0046(14) _cell_length_b 6.1040(14) _cell_length_c 12.099(3) _cell_measurement_reflns_used 2328 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 54.642 _cell_measurement_theta_min 6.917 _cell_volume 431.84(18) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 100 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker smart1000ccd' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4884 _diffrn_reflns_theta_full 27.53 _diffrn_reflns_theta_max 27.53 _diffrn_reflns_theta_min 1.73 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_T_max 0.9802 _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 184 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.228 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.036 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 1080 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.106 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0319 _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^)+(0.0567P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0832 _refine_ls_wR_factor_ref 0.0855 _reflns_number_gt 986 _reflns_number_total 1080 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file C0OB01019G.TXT _[local]_cod_data_source_block oic1m _[local]_cod_cif_authors_sg_H-M P2(1) _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius ; _cod_original_cell_volume 431.83(17) _cod_database_code 7151726 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, 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 N1 N 0.3831(3) 0.1901(3) 0.83126(15) 0.0297(4) Uani 1 1 d . . . H1A H 0.4850 0.2405 0.7957 0.036 Uiso 1 1 calc R . . O1 O 0.2123(2) -0.0450(2) 0.92196(11) 0.0275(3) Uani 1 1 d . . . O2 O 0.5503(2) -0.1415(3) 0.88630(12) 0.0359(4) Uani 1 1 d . . . O3 O -0.2818(2) 0.4955(3) 0.79891(11) 0.0298(3) Uani 1 1 d . . . H3A H -0.3378 0.6019 0.8273 0.045 Uiso 1 1 calc R . . C1 C 0.3986(3) -0.0061(3) 0.87963(15) 0.0239(4) Uani 1 1 d . . . C2 C 0.0667(3) 0.1471(3) 0.90683(15) 0.0235(4) Uani 1 1 d . . . H2A H 0.0542 0.2068 0.9813 0.028 Uiso 1 1 calc R . . H2B H -0.0885 0.1103 0.8624 0.028 Uiso 1 1 calc R . . C3 C 0.1818(3) 0.3152(3) 0.84225(14) 0.0209(4) Uani 1 1 d . . . H3B H 0.2313 0.4455 0.8918 0.025 Uiso 1 1 calc R . . C4 C 0.0445(3) 0.3920(3) 0.72599(15) 0.0211(4) Uani 1 1 d . . . H4A H 0.1572 0.4565 0.6857 0.025 Uiso 1 1 calc R . . C5 C -0.1205(3) 0.5743(3) 0.73768(15) 0.0223(4) Uani 1 1 d . . . H5A H -0.0348 0.6998 0.7785 0.027 Uiso 1 1 calc R . . H5B H -0.2020 0.6251 0.6615 0.027 Uiso 1 1 calc R . . C6 C -0.0765(3) 0.2040(3) 0.65056(16) 0.0260(4) Uani 1 1 d . . . H6A H 0.0255 0.0747 0.6600 0.031 Uiso 1 1 calc R . . H6B H -0.2168 0.1625 0.6755 0.031 Uiso 1 1 calc R . . C7 C -0.1392(3) 0.2677(3) 0.52739(15) 0.0303(4) Uani 1 1 d . . . H7A H -0.0177 0.2901 0.4902 0.036 Uiso 1 1 calc R . . C8 C -0.3489(4) 0.2948(4) 0.46706(17) 0.0426(6) Uani 1 1 d . . . H8C H -0.4751 0.2739 0.5012 0.051 Uiso 1 1 calc R . . H8A H -0.3743 0.3353 0.3894 0.051 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 N1 0.0216(7) 0.0328(10) 0.0377(9) 0.0099(7) 0.0128(7) 0.0050(7) O1 0.0258(6) 0.0209(8) 0.0368(7) 0.0042(6) 0.0093(6) 0.0032(6) O2 0.0316(7) 0.0301(8) 0.0450(8) -0.0058(7) 0.0065(6) 0.0104(7) O3 0.0307(7) 0.0231(7) 0.0406(8) -0.0020(6) 0.0184(6) 0.0023(6) C1 0.0225(8) 0.0251(9) 0.0223(8) -0.0055(8) 0.0015(7) 0.0008(8) C2 0.0235(8) 0.0221(9) 0.0259(9) 0.0043(7) 0.0079(7) 0.0020(7) C3 0.0178(8) 0.0207(9) 0.0244(8) 0.0013(7) 0.0049(6) -0.0007(7) C4 0.0223(8) 0.0179(9) 0.0240(8) 0.0007(7) 0.0070(7) -0.0018(7) C5 0.0244(9) 0.0182(9) 0.0235(8) 0.0008(7) 0.0033(7) 0.0002(7) C6 0.0314(10) 0.0208(10) 0.0268(9) -0.0026(7) 0.0085(8) -0.0005(8) C7 0.0395(11) 0.0269(10) 0.0250(9) -0.0035(8) 0.0087(8) -0.0016(9) C8 0.0464(13) 0.0449(15) 0.0322(11) -0.0062(11) -0.0002(10) -0.0043(12) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C3 114.10(16) . . ? C1 N1 H1A 123.0 . . ? C3 N1 H1A 123.0 . . ? C1 O1 C2 109.70(15) . . ? C5 O3 H3A 109.5 . . ? O2 C1 N1 128.17(18) . . ? O2 C1 O1 121.71(18) . . ? N1 C1 O1 110.11(16) . . ? O1 C2 C3 105.94(13) . . ? O1 C2 H2A 110.5 . . ? C3 C2 H2A 110.5 . . ? O1 C2 H2B 110.5 . . ? C3 C2 H2B 110.5 . . ? H2A C2 H2B 108.7 . . ? N1 C3 C4 111.09(14) . . ? N1 C3 C2 100.00(14) . . ? C4 C3 C2 117.26(14) . . ? N1 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? C5 C4 C3 111.41(14) . . ? C5 C4 C6 111.79(15) . . ? C3 C4 C6 113.46(16) . . ? C5 C4 H4A 106.6 . . ? C3 C4 H4A 106.6 . . ? C6 C4 H4A 106.6 . . ? O3 C5 C4 109.58(15) . . ? O3 C5 H5A 109.8 . . ? C4 C5 H5A 109.8 . . ? O3 C5 H5B 109.8 . . ? C4 C5 H5B 109.8 . . ? H5A C5 H5B 108.2 . . ? C7 C6 C4 111.88(16) . . ? C7 C6 H6A 109.2 . . ? C4 C6 H6A 109.2 . . ? C7 C6 H6B 109.2 . . ? C4 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C6 125.12(19) . . ? C8 C7 H7A 117.4 . . ? C6 C7 H7A 117.4 . . ? C7 C8 H8C 120.0 . . ? C7 C8 H8A 120.0 . . ? H8C C8 H8A 120.0 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.327(3) . ? N1 C3 1.461(2) . ? N1 H1A 0.8800 . ? O1 C1 1.353(2) . ? O1 C2 1.449(2) . ? O2 C1 1.219(2) . ? O3 C5 1.430(2) . ? O3 H3A 0.8400 . ? C2 C3 1.545(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.533(2) . ? C3 H3B 1.0000 . ? C4 C5 1.517(3) . ? C4 C6 1.541(3) . ? C4 H4A 1.0000 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.503(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.315(3) . ? C7 H7A 0.9500 . ? C8 H8C 0.9500 . ? C8 H8A 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 N1 H1A O3 0.88 2.09 2.835(2) 142.1 1_655 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 C1 O2 -177.77(18) . . . . ? C3 N1 C1 O1 3.6(2) . . . . ? C2 O1 C1 O2 177.36(17) . . . . ? C2 O1 C1 N1 -3.9(2) . . . . ? C1 O1 C2 C3 2.71(18) . . . . ? C1 N1 C3 C4 -126.21(18) . . . . ? C1 N1 C3 C2 -1.7(2) . . . . ? O1 C2 C3 N1 -0.64(17) . . . . ? O1 C2 C3 C4 119.48(16) . . . . ? N1 C3 C4 C5 -163.15(15) . . . . ? C2 C3 C4 C5 82.8(2) . . . . ? N1 C3 C4 C6 69.64(19) . . . . ? C2 C3 C4 C6 -44.5(2) . . . . ? C3 C4 C5 O3 -61.83(19) . . . . ? C6 C4 C5 O3 66.29(18) . . . . ? C5 C4 C6 C7 72.64(19) . . . . ? C3 C4 C6 C7 -160.34(15) . . . . ? C4 C6 C7 C8 -111.9(2) . . . . ? _journal_paper_doi 10.1039/C0OB01019G