data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Mark Moloney' 'Syed Raziullah Hussaini' _publ_contact_author_name 'Dr Mark Moloney' _publ_contact_author_address ; Chemistry University of Oxford Dyson Perrins Laboratory South Parks Rd Oxford UK OX1 3QY UNITED KINGDOM ; _publ_contact_author_email MARK.MOLONEY@CHEM.OX.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; 2,5-Disubstituted Pyrrolidines: Versatile Regioselective and Diastereoselective Synthesis by Enamine Reduction and Subsequent Alkylation ; data_cis-5b.cif _database_code_CSD 209273 #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _chemical_absolute_configuration syn #============================================================= _cell_length_a 11.5590(3) _cell_angle_alpha 90 _cell_length_b 11.8196(3) _cell_angle_beta 90 _cell_length_c 15.3885(4) _cell_angle_gamma 90 _cell_volume 2102.4 _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C21 H27 N1 O7 ' _chemical_formula_moiety ' C21 H27 N1 O7 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 405.45 _cell_measurement_reflns_used 11033 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 4 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.28 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_max 0.42 _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_meas ? _exptl_crystal_F_000 864. _exptl_absorpt_coefficient_mu 0.096 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.97 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 11033 _reflns_number_total 2696 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_gt 1900 _diffrn_reflns_theta_min 5.11 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min 0 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _refine_diff_density_min -0.14 _refine_diff_density_max 0.12 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 1900 _refine_ls_number_parameters 262 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0346 _refine_ls_goodness_of_fit_ref 1.0751 _refine_ls_shift/su_max 0.036722 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 0.485 0.213 0.256 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type N1 0.14186(14) 0.36267(14) 0.32769(11) 0.0276 1.0000 Uani C1 0.12010(16) 0.47063(17) 0.28248(14) 0.0287 1.0000 Uani C2 0.14836(19) 0.44570(19) 0.18669(14) 0.0340 1.0000 Uani C3 0.14514(17) 0.3166(2) 0.17920(14) 0.0324 1.0000 Uani C4 0.18678(17) 0.27603(17) 0.26879(14) 0.0292 1.0000 Uani C5 0.07958(17) 0.33775(18) 0.40064(13) 0.0298 1.0000 Uani O1 0.01089(13) 0.40600(14) 0.43189(11) 0.0395 1.0000 Uani C6 0.10231(17) 0.22715(18) 0.44435(14) 0.0298 1.0000 Uani C7 0.00879(18) 0.16108(19) 0.47162(14) 0.0339 1.0000 Uani C8 0.0278(2) 0.0615(2) 0.51741(15) 0.0388 1.0000 Uani C9 0.1404(2) 0.0291(2) 0.53728(15) 0.0419 1.0000 Uani C10 0.2337(2) 0.0940(2) 0.51118(15) 0.0416 1.0000 Uani C11 0.21472(18) 0.1927(2) 0.46445(14) 0.0347 1.0000 Uani C12 0.19746(17) 0.56577(18) 0.31839(14) 0.0288 1.0000 Uani C13 0.18306(18) 0.58465(18) 0.41558(14) 0.0309 1.0000 Uani O2 0.24647(15) 0.54593(15) 0.46994(11) 0.0445 1.0000 Uani O3 0.09150(13) 0.65077(13) 0.43284(9) 0.0335 1.0000 Uani C14 0.0623(2) 0.6626(2) 0.52421(15) 0.0448 1.0000 Uani C15 -0.0579(2) 0.7050(3) 0.52976(16) 0.0579 1.0000 Uani C16 0.17233(17) 0.67496(18) 0.27002(14) 0.0291 1.0000 Uani O4 0.08543(14) 0.69458(14) 0.2297(1) 0.0394 1.0000 Uani O5 0.26051(12) 0.74710(12) 0.2792(1) 0.0356 1.0000 Uani C17 0.2446(3) 0.8597(2) 0.24193(18) 0.0529 1.0000 Uani C18 0.1871(3) 0.9350(2) 0.3071(3) 0.0657 1.0000 Uani C19 0.31870(17) 0.27034(19) 0.27033(14) 0.0311 1.0000 Uani O6 0.38199(13) 0.34815(15) 0.28497(13) 0.0465 1.0000 Uani O7 0.35283(13) 0.16635(14) 0.24851(11) 0.0428 1.0000 Uani C20 0.47692(19) 0.1433(2) 0.25078(17) 0.0462 1.0000 Uani C21 0.5147(3) 0.1166(4) 0.3402(2) 0.0707 1.0000 Uani H11 0.0388 0.4975 0.2906 0.0344 1.0000 Uiso H21 0.2268 0.4752 0.1714 0.0408 1.0000 Uiso H22 0.0893 0.4808 0.1476 0.0408 1.0000 Uiso H31 0.1982 0.2897 0.1322 0.0389 1.0000 Uiso H32 0.0648 0.2894 0.1671 0.0389 1.0000 Uiso H41 0.1597 0.1985 0.2849 0.0350 1.0000 Uiso H71 -0.0720 0.1856 0.4581 0.0406 1.0000 Uiso H81 -0.0391 0.0135 0.5359 0.0465 1.0000 Uiso H91 0.1541 -0.0421 0.5709 0.0503 1.0000 Uiso H101 0.3143 0.0700 0.5259 0.0499 1.0000 Uiso H111 0.2820 0.2395 0.4451 0.0417 1.0000 Uiso H121 0.2794 0.5416 0.3090 0.0345 1.0000 Uiso H141 0.1162 0.7174 0.5526 0.0538 1.0000 Uiso H142 0.0683 0.5875 0.5538 0.0538 1.0000 Uiso H151 -0.0802 0.7139 0.5922 0.0694 1.0000 Uiso H152 -0.0634 0.7799 0.4998 0.0694 1.0000 Uiso H153 -0.1113 0.6499 0.5011 0.0694 1.0000 Uiso H171 0.3217 0.8920 0.2260 0.0634 1.0000 Uiso H172 0.1952 0.8541 0.1888 0.0634 1.0000 Uiso H181 0.1762 1.0120 0.2815 0.0788 1.0000 Uiso H182 0.2365 0.9406 0.3602 0.0788 1.0000 Uiso H183 0.1100 0.9026 0.3230 0.0788 1.0000 Uiso H201 0.5198 0.2114 0.2296 0.0554 1.0000 Uiso H202 0.4943 0.0775 0.2121 0.0554 1.0000 Uiso H211 0.5998 0.1011 0.3404 0.0848 1.0000 Uiso H212 0.4978 0.1824 0.3791 0.0848 1.0000 Uiso H213 0.4723 0.0484 0.3616 0.0848 1.0000 Uiso 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 0.0250(8) 0.0269(8) 0.0309(8) -0.0034(7) 0.0034(7) -0.0031(7) C1 0.0242(9) 0.028(1) 0.034(1) 0.0004(9) -0.0004(8) 0.0003(8) C2 0.0362(11) 0.0348(11) 0.031(1) 0.0000(9) -0.0017(9) -0.0028(9) C3 0.027(1) 0.0378(11) 0.033(1) -0.007(1) 0.0023(9) -0.0023(9) C4 0.0256(9) 0.026(1) 0.0358(11) -0.0030(9) 0.0047(9) -0.0017(8) C5 0.0259(9) 0.0305(11) 0.033(1) -0.0044(9) 0.0032(9) -0.0049(9) O1 0.0361(8) 0.0361(8) 0.0462(8) -0.0036(7) 0.0132(7) 0.0018(7) C6 0.0279(9) 0.033(1) 0.0281(9) -0.0059(9) 0.0031(9) -0.0040(8) C7 0.028(1) 0.0391(12) 0.0349(11) -0.003(1) 0.0049(9) -0.0060(9) C8 0.0414(12) 0.0399(12) 0.0350(11) 0.000(1) 0.006(1) -0.011(1) C9 0.0493(13) 0.0410(12) 0.0354(11) 0.006(1) -0.003(1) -0.0030(11) C10 0.0338(11) 0.0540(15) 0.0369(11) 0.0034(11) -0.006(1) 0.0008(11) C11 0.030(1) 0.0421(12) 0.0323(11) -0.001(1) -0.0020(8) -0.0049(9) C12 0.0235(9) 0.028(1) 0.035(1) -0.0019(9) -0.0004(8) 0.0007(8) C13 0.0282(9) 0.028(1) 0.0367(11) -0.0010(9) -0.0042(9) -0.0021(9) O2 0.0394(9) 0.053(1) 0.0412(8) 0.0031(8) -0.0115(7) 0.0066(8) O3 0.0397(8) 0.0329(8) 0.0281(7) -0.0004(7) -0.0011(6) 0.0051(7) C14 0.0546(14) 0.0531(15) 0.027(1) -0.0029(11) -0.002(1) 0.0060(12) C15 0.0517(15) 0.087(2) 0.0348(12) -0.0104(14) 0.0050(11) 0.0092(15) C16 0.030(1) 0.029(1) 0.028(1) -0.0020(9) 0.0028(8) 0.0009(8) O4 0.0422(8) 0.0361(8) 0.0398(8) 0.0017(7) -0.0095(7) 0.0025(7) O5 0.0326(7) 0.0306(8) 0.0436(8) 0.0034(7) 0.0020(7) -0.0046(7) C17 0.0622(16) 0.0375(13) 0.0589(16) 0.0197(12) -0.0058(14) -0.0123(13) C18 0.0552(16) 0.0313(13) 0.111(3) -0.0058(16) -0.0156(18) 0.0010(13) C19 0.0272(9) 0.0356(11) 0.031(1) 0.001(1) 0.0033(9) 0.0008(9) O6 0.0295(8) 0.0414(9) 0.0686(11) -0.0039(9) -0.0035(8) -0.0042(7) O7 0.0296(7) 0.0422(9) 0.057(1) -0.0107(8) 0.0061(7) 0.0059(7) C20 0.0309(11) 0.0553(15) 0.0524(14) -0.0043(13) 0.0073(11) 0.0128(11) C21 0.0501(15) 0.102(3) 0.0595(17) 0.0236(18) 0.0110(14) 0.0334(18) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.475(3) yes N1 . C4 . 1.463(3) yes N1 . C5 . 1.366(3) yes C1 . C2 . 1.538(3) yes C1 . C12 . 1.539(3) yes C1 . H11 . 1.0001 no C2 . C3 . 1.530(3) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C4 . 1.537(3) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . C19 . 1.527(3) yes C4 . H41 . 1.000 no C5 . O1 . 1.230(3) yes C5 . C6 . 1.493(3) yes C6 . C7 . 1.398(3) yes C6 . C11 . 1.396(3) yes C7 . C8 . 1.389(3) yes C7 . H71 . 1.000 no C8 . C9 . 1.391(4) yes C8 . H81 . 1.000 no C9 . C10 . 1.383(3) yes C9 . H91 . 1.000 no C10 . C11 . 1.388(3) yes C10 . H101 . 1.000 no C11 . H111 . 1.000 no C12 . C13 . 1.521(3) yes C12 . C16 . 1.518(3) yes C12 . H121 . 1.000 no C13 . O2 . 1.203(3) yes C13 . O3 . 1.342(3) yes O3 . C14 . 1.453(3) yes C14 . C15 . 1.479(4) yes C14 . H141 . 1.000 no C14 . H142 . 1.000 no C15 . H151 . 1.000 no C15 . H152 . 1.000 no C15 . H153 . 1.000 no C16 . O4 . 1.203(3) yes C16 . O5 . 1.336(2) yes O5 . C17 . 1.460(3) yes C17 . C18 . 1.496(5) yes C17 . H171 . 1.000 no C17 . H172 . 1.000 no C18 . H181 . 1.000 no C18 . H182 . 1.000 no C18 . H183 . 1.000 no C19 . O6 . 1.196(3) yes C19 . O7 . 1.334(3) yes O7 . C20 . 1.460(3) yes C20 . C21 . 1.478(4) yes C20 . H201 . 1.000 no C20 . H202 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C4 . 111.96(16) yes C1 . N1 . C5 . 118.97(17) yes C4 . N1 . C5 . 123.06(17) yes N1 . C1 . C2 . 104.48(16) yes N1 . C1 . C12 . 111.32(16) yes C2 . C1 . C12 . 111.13(17) yes N1 . C1 . H11 . 112.13 no C2 . C1 . H11 . 112.32 no C12 . C1 . H11 . 105.61 no C1 . C2 . C3 . 104.95(17) yes C1 . C2 . H21 . 110.59 no C3 . C2 . H21 . 110.6 no C1 . C2 . H22 . 110.59 no C3 . C2 . H22 . 110.60 no H21 . C2 . H22 . 109.5 no C2 . C3 . C4 . 103.65(17) yes C2 . C3 . H31 . 110.9 no C4 . C3 . H31 . 110.91 no C2 . C3 . H32 . 110.9 no C4 . C3 . H32 . 110.91 no H31 . C3 . H32 . 109.5 no N1 . C4 . C3 . 103.07(16) yes N1 . C4 . C19 . 112.08(17) yes C3 . C4 . C19 . 109.91(17) yes N1 . C4 . H41 . 112.15 no C3 . C4 . H41 . 114.23 no C19 . C4 . H41 . 105.58 no N1 . C5 . O1 . 121.35(19) yes N1 . C5 . C6 . 117.79(18) yes O1 . C5 . C6 . 120.78(18) yes C5 . C6 . C7 . 119.22(18) yes C5 . C6 . C11 . 121.23(18) yes C7 . C6 . C11 . 119.4(2) yes C6 . C7 . C8 . 120.2(2) yes C6 . C7 . H71 . 119.9 no C8 . C7 . H71 . 119.9 no C7 . C8 . C9 . 119.5(2) yes C7 . C8 . H81 . 120.2 no C9 . C8 . H81 . 120.2 no C8 . C9 . C10 . 120.9(2) yes C8 . C9 . H91 . 119.6 no C10 . C9 . H91 . 119.6 no C9 . C10 . C11 . 119.6(2) yes C9 . C10 . H101 . 120.2 no C11 . C10 . H101 . 120.2 no C6 . C11 . C10 . 120.4(2) yes C6 . C11 . H111 . 119.8 no C10 . C11 . H111 . 119.8 no C1 . C12 . C13 . 113.36(17) yes C1 . C12 . C16 . 109.51(16) yes C13 . C12 . C16 . 109.66(17) yes C1 . C12 . H121 . 106.84 no C13 . C12 . H121 . 106.68 no C16 . C12 . H121 . 110.74 no C12 . C13 . O2 . 124.1(2) yes C12 . C13 . O3 . 111.49(17) yes O2 . C13 . O3 . 124.4(2) yes C13 . O3 . C14 . 115.52(17) yes O3 . C14 . C15 . 107.9(2) yes O3 . C14 . H141 . 109.9 no C15 . C14 . H141 . 109.9 no O3 . C14 . H142 . 109.9 no C15 . C14 . H142 . 109.9 no H141 . C14 . H142 . 109.5 no C14 . C15 . H151 . 109.5 no C14 . C15 . H152 . 109.5 no H151 . C15 . H152 . 109.5 no C14 . C15 . H153 . 109.5 no H151 . C15 . H153 . 109.5 no H152 . C15 . H153 . 109.5 no C12 . C16 . O4 . 125.21(19) yes C12 . C16 . O5 . 110.18(17) yes O4 . C16 . O5 . 124.61(19) yes C16 . O5 . C17 . 116.37(18) yes O5 . C17 . C18 . 109.6(2) yes O5 . C17 . H171 . 109.5 no C18 . C17 . H171 . 109.5 no O5 . C17 . H172 . 109.4 no C18 . C17 . H172 . 109.4 no H171 . C17 . H172 . 109.5 no C17 . C18 . H181 . 109.5 no C17 . C18 . H182 . 109.5 no H181 . C18 . H182 . 109.5 no C17 . C18 . H183 . 109.5 no H181 . C18 . H183 . 109.5 no H182 . C18 . H183 . 109.5 no C4 . C19 . O6 . 125.4(2) yes C4 . C19 . O7 . 109.40(18) yes O6 . C19 . O7 . 125.09(19) yes C19 . O7 . C20 . 117.16(19) yes O7 . C20 . C21 . 110.6(2) yes O7 . C20 . H201 . 109.2 no C21 . C20 . H201 . 109.2 no O7 . C20 . H202 . 109.2 no C21 . C20 . H202 . 109.2 no H201 . C20 . H202 . 109.5 no C20 . C21 . H211 . 109.5 no C20 . C21 . H212 . 109.5 no H211 . C21 . H212 . 109.5 no C20 . C21 . H213 . 109.5 no H211 . C21 . H213 . 109.5 no H212 . C21 . H213 . 109.5 no data_cpd-7b.cif _database_code_CSD 209274 #========================================================================== # Diffractometer details #========================================================================== _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #========================================================================== # General computing #========================================================================== _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _chemical_absolute_configuration syn #============================================================= _cell_length_a 5.8063(2) _cell_angle_alpha 90 _cell_length_b 16.1078(2) _cell_angle_beta 90 _cell_length_c 22.7170(4) _cell_angle_gamma 90 _cell_volume 2124.6 _symmetry_cell_setting 'Orthorhombic ' _symmetry_space_group_name_H-M 'P 21 21 21 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C22 H29 N1 O7 ' _chemical_formula_moiety ' C22 H29 N1 O7 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 419.47 _cell_measurement_reflns_used 15693 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 4 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.36 _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 896.301 _exptl_absorpt_coefficient_mu 0.098 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.97 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 15693 _reflns_number_total 2808 # 2835 unique reflections including systematic absences _diffrn_reflns_av_R_equivalents 0.052 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_gt 2232 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 27.51 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _reflns_limit_h_min 0 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 29 _refine_diff_density_min -0.31 _refine_diff_density_max 0.18 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 2232 _refine_ls_number_parameters 271 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.0492 _refine_ls_goodness_of_fit_ref 1.0012 _refine_ls_shift/su_max 0.010876 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 0.872 0.421 0.511 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type N1 0.3480(3) 0.55355(11) 0.41840(8) 0.0206 1.0000 Uani C1 0.2875(4) 0.64182(13) 0.40969(9) 0.0207 1.0000 Uani C2 0.4037(5) 0.68505(14) 0.4620(1) 0.0270 1.0000 Uani C3 0.6096(5) 0.62985(15) 0.47795(11) 0.0324 1.0000 Uani C4 0.5313(4) 0.54094(14) 0.46223(9) 0.0237 1.0000 Uani C5 0.1929(4) 0.49403(14) 0.40343(9) 0.0218 1.0000 Uani O1 0.0041(3) 0.5106(1) 0.38182(7) 0.0270 1.0000 Uani C6 0.2623(4) 0.40507(14) 0.41210(9) 0.0232 1.0000 Uani C7 0.4689(5) 0.37513(15) 0.39026(11) 0.0304 1.0000 Uani C8 0.5177(5) 0.28992(17) 0.39423(13) 0.0381 1.0000 Uani C9 0.3627(6) 0.23702(16) 0.42017(12) 0.0377 1.0000 Uani C10 0.1572(5) 0.26670(16) 0.44270(12) 0.0347 1.0000 Uani C11 0.1053(5) 0.35092(15) 0.43824(11) 0.0282 1.0000 Uani C12 0.3695(4) 0.67391(14) 0.3483(1) 0.0227 1.0000 Uani C13 0.6333(6) 0.6831(2) 0.34479(14) 0.0428 1.0000 Uani C14 0.2600(5) 0.75892(14) 0.3373(1) 0.0257 1.0000 Uani O2 0.1304(4) 0.79397(11) 0.37021(8) 0.0335 1.0000 Uani O3 0.3312(4) 0.78938(11) 0.28578(8) 0.0344 1.0000 Uani C15 0.2230(6) 0.86622(16) 0.26570(12) 0.0403 1.0000 Uani C16 -0.0006(7) 0.84761(17) 0.23401(13) 0.0489 1.0000 Uani C17 0.2874(4) 0.61336(14) 0.3007(1) 0.0247 1.0000 Uani O4 0.3988(4) 0.55505(12) 0.28399(8) 0.0375 1.0000 Uani O5 0.0780(3) 0.63292(11) 0.28194(8) 0.0319 1.0000 Uani C18 -0.0348(6) 0.57493(16) 0.24199(13) 0.0387 1.0000 Uani C19 -0.1363(8) 0.6220(2) 0.19185(14) 0.0587 1.0000 Uani C20 0.4464(5) 0.49862(15) 0.5182(1) 0.0276 1.0000 Uani O6 0.5703(4) 0.45598(14) 0.54844(9) 0.0435 1.0000 Uani O7 0.2290(3) 0.51754(11) 0.53062(7) 0.0298 1.0000 Uani C21 0.1375(5) 0.48923(18) 0.58717(11) 0.0367 1.0000 Uani C22 0.1639(7) 0.5561(2) 0.63146(13) 0.0506 1.0000 Uani H11 0.1180 0.6528 0.4090 0.0248 1.0000 Uiso H21 0.4570 0.7418 0.4506 0.0324 1.0000 Uiso H22 0.2948 0.6893 0.4959 0.0324 1.0000 Uiso H31 0.6456 0.6342 0.5209 0.0389 1.0000 Uiso H32 0.7484 0.6458 0.4545 0.0389 1.0000 Uiso H41 0.6549 0.5043 0.4459 0.0284 1.0000 Uiso H71 0.5824 0.4139 0.3718 0.0365 1.0000 Uiso H81 0.6657 0.2677 0.3781 0.0458 1.0000 Uiso H91 0.3987 0.1764 0.4228 0.0453 1.0000 Uiso H101 0.0464 0.2279 0.4621 0.0417 1.0000 Uiso H111 -0.0444 0.3725 0.4537 0.0339 1.0000 Uiso H131 0.6772 0.7038 0.3048 0.0514 1.0000 Uiso H132 0.6864 0.7236 0.3753 0.0514 1.0000 Uiso H133 0.7073 0.6280 0.3520 0.0514 1.0000 Uiso H151 0.1906 0.9025 0.3004 0.0483 1.0000 Uiso H152 0.3299 0.8956 0.2382 0.0483 1.0000 Uiso H161 -0.0724 0.9008 0.2206 0.0587 1.0000 Uiso H162 -0.1082 0.8183 0.2614 0.0587 1.0000 Uiso H163 0.0312 0.8115 0.1992 0.0587 1.0000 Uiso H181 -0.1595 0.5446 0.2635 0.0464 1.0000 Uiso H182 0.0806 0.5342 0.2268 0.0464 1.0000 Uiso H191 -0.2139 0.5825 0.1643 0.0704 1.0000 Uiso H192 -0.2515 0.6628 0.2071 0.0704 1.0000 Uiso H193 -0.0114 0.6523 0.1705 0.0704 1.0000 Uiso H211 0.2241 0.4389 0.6004 0.0441 1.0000 Uiso H212 -0.0293 0.4751 0.5827 0.0441 1.0000 Uiso H221 0.1014 0.5368 0.6701 0.0607 1.0000 Uiso H222 0.3307 0.5702 0.6359 0.0607 1.0000 Uiso H223 0.0773 0.6064 0.6182 0.0607 1.0000 Uiso 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 0.0213(9) 0.0179(8) 0.0226(8) -0.0002(7) -0.0009(7) 0.0017(8) C1 0.020(1) 0.0175(9) 0.024(1) 0.0014(8) 0.0016(9) 0.0005(9) C2 0.0325(12) 0.021(1) 0.0275(11) -0.0031(8) -0.001(1) -0.001(1) C3 0.0334(13) 0.0273(11) 0.0365(12) 0.001(1) -0.0117(11) -0.0068(11) C4 0.020(1) 0.024(1) 0.027(1) -0.0002(8) -0.0029(9) 0.0018(9) C5 0.021(1) 0.024(1) 0.0204(9) 0.0001(8) 0.0031(8) 0.0001(9) O1 0.0229(8) 0.0258(8) 0.0323(8) 0.0024(6) -0.0035(7) -0.0012(7) C6 0.0267(11) 0.022(1) 0.021(1) -0.0017(8) -0.0045(9) -0.001(1) C7 0.0309(13) 0.0266(11) 0.0337(11) -0.0032(9) 0.0004(11) 0.0006(11) C8 0.0363(14) 0.0315(13) 0.0466(14) -0.0102(11) -0.0025(13) 0.0089(12) C9 0.0523(18) 0.0216(11) 0.0393(13) -0.002(1) -0.0102(13) 0.0068(13) C10 0.0451(16) 0.0242(11) 0.0349(12) 0.004(1) -0.0035(12) -0.0043(12) C11 0.0287(12) 0.0257(11) 0.0303(11) 0.0008(9) -0.001(1) -0.003(1) C12 0.0240(11) 0.021(1) 0.023(1) 0.0007(9) 0.0009(9) 0.001(1) C13 0.0402(16) 0.0444(16) 0.0438(16) 0.0043(13) 0.0036(13) 0.0019(14) C14 0.0284(12) 0.020(1) 0.028(1) 0.0021(9) -0.006(1) -0.004(1) O2 0.0408(11) 0.0260(8) 0.0336(8) -0.0004(7) -0.0010(8) 0.0085(8) O3 0.0466(12) 0.0272(8) 0.0294(8) 0.0085(7) 0.0005(8) 0.0004(9) C15 0.0604(19) 0.0228(11) 0.0376(13) 0.0110(11) -0.0100(14) -0.0037(13) C16 0.072(2) 0.0313(13) 0.0440(15) 0.0057(11) -0.0232(17) 0.0031(16) C17 0.0289(12) 0.023(1) 0.023(1) 0.0026(8) 0.001(1) 0.002(1) O4 0.0421(11) 0.0341(9) 0.0363(9) -0.0097(8) 0.0013(9) 0.0054(9) O5 0.034(1) 0.0242(8) 0.0373(9) -0.0042(7) -0.0104(8) -0.0006(8) C18 0.0438(17) 0.0315(12) 0.0407(14) -0.0056(11) -0.0137(13) -0.0048(13) C19 0.089(3) 0.0478(16) 0.0394(15) -0.0030(13) -0.0273(19) -0.010(2) C20 0.0298(12) 0.0248(11) 0.0281(11) 0.0009(9) -0.0052(9) -0.002(1) O6 0.0387(11) 0.0482(11) 0.044(1) 0.0176(9) -0.0074(9) 0.005(1) O7 0.0308(9) 0.0334(9) 0.0252(8) 0.0039(7) 0.0023(7) 0.0015(8) C21 0.0413(15) 0.0407(14) 0.0283(12) 0.0071(11) 0.0034(11) -0.0072(13) C22 0.063(2) 0.0543(18) 0.0341(13) -0.0042(13) 0.0113(15) -0.0040(18) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.478(3) yes N1 . C4 . 1.472(3) yes N1 . C5 . 1.359(3) yes C1 . C2 . 1.533(3) yes C1 . C12 . 1.561(3) yes C1 . H11 . 1.000 no C2 . C3 . 1.533(4) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C4 . 1.544(3) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . C20 . 1.524(3) yes C4 . H41 . 1.000 no C5 . O1 . 1.230(3) yes C5 . C6 . 1.502(3) yes C6 . C7 . 1.385(4) yes C6 . C11 . 1.395(3) yes C7 . C8 . 1.404(4) yes C7 . H71 . 1.000 no C8 . C9 . 1.372(4) yes C8 . H81 . 1.000 no C9 . C10 . 1.384(5) yes C9 . H91 . 1.000 no C10 . C11 . 1.393(4) yes C10 . H101 . 1.000 no C11 . H111 . 1.000 no C12 . C13 . 1.541(4) yes C12 . C14 . 1.530(3) yes C12 . C17 . 1.533(3) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no C14 . O2 . 1.202(3) yes C14 . O3 . 1.334(3) yes O3 . C15 . 1.461(3) yes C15 . C16 . 1.515(5) yes C15 . H151 . 1.000 no C15 . H152 . 1.000 no C16 . H161 . 1.000 no C16 . H162 . 1.000 no C16 . H163 . 1.000 no C17 . O4 . 1.202(3) yes C17 . O5 . 1.326(3) yes O5 . C18 . 1.458(3) yes C18 . C19 . 1.489(4) yes C18 . H181 . 1.000 no C18 . H182 . 1.000 no C19 . H191 . 1.000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no C20 . O6 . 1.209(3) yes C20 . O7 . 1.329(3) yes O7 . C21 . 1.463(3) yes C21 . C22 . 1.482(4) yes C21 . H211 . 1.000 no C21 . H212 . 1.000 no C22 . H221 . 1.000 no C22 . H222 . 1.000 no C22 . H223 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C4 . 113.28(17) yes C1 . N1 . C5 . 119.19(19) yes C4 . N1 . C5 . 123.47(18) yes N1 . C1 . C2 . 103.21(17) yes N1 . C1 . C12 . 111.45(18) yes C2 . C1 . C12 . 114.03(19) yes N1 . C1 . H11 . 113.98 no C2 . C1 . H11 . 111.39 no C12 . C1 . H11 . 103.15 no C1 . C2 . C3 . 105.24(18) yes C1 . C2 . H21 . 110.5 no C3 . C2 . H21 . 110.5 no C1 . C2 . H22 . 110.5 no C3 . C2 . H22 . 110.5 no H21 . C2 . H22 . 109.5 no C2 . C3 . C4 . 104.69(19) yes C2 . C3 . H31 . 110.7 no C4 . C3 . H31 . 110.7 no C2 . C3 . H32 . 110.7 no C4 . C3 . H32 . 110.7 no H31 . C3 . H32 . 109.5 no N1 . C4 . C3 . 103.97(18) yes N1 . C4 . C20 . 113.1(2) yes C3 . C4 . C20 . 108.49(19) yes N1 . C4 . H41 . 110.47 no C3 . C4 . H41 . 114.9 no C20 . C4 . H41 . 106.11 no N1 . C5 . O1 . 122.5(2) yes N1 . C5 . C6 . 117.5(2) yes O1 . C5 . C6 . 119.9(2) yes C5 . C6 . C7 . 121.2(2) yes C5 . C6 . C11 . 118.5(2) yes C7 . C6 . C11 . 120.1(2) yes C6 . C7 . C8 . 119.5(2) yes C6 . C7 . H71 . 120.3 no C8 . C7 . H71 . 120.3 no C7 . C8 . C9 . 120.1(3) yes C7 . C8 . H81 . 119.9 no C9 . C8 . H81 . 119.9 no C8 . C9 . C10 . 120.6(2) yes C8 . C9 . H91 . 119.7 no C10 . C9 . H91 . 119.7 no C9 . C10 . C11 . 119.7(3) yes C9 . C10 . H101 . 120.1 no C11 . C10 . H101 . 120.1 no C6 . C11 . C10 . 119.9(3) yes C6 . C11 . H111 . 120.1 no C10 . C11 . H111 . 120.1 no C1 . C12 . C13 . 112.4(2) yes C1 . C12 . C14 . 108.42(18) yes C13 . C12 . C14 . 108.5(2) yes C1 . C12 . C17 . 108.98(19) yes C13 . C12 . C17 . 109.5(2) yes C14 . C12 . C17 . 108.91(18) yes C12 . C13 . H131 . 109.5 no C12 . C13 . H132 . 109.5 no H131 . C13 . H132 . 109.5 no C12 . C13 . H133 . 109.5 no H131 . C13 . H133 . 109.5 no H132 . C13 . H133 . 109.5 no C12 . C14 . O2 . 125.3(2) yes C12 . C14 . O3 . 110.1(2) yes O2 . C14 . O3 . 124.5(2) yes C14 . O3 . C15 . 116.9(2) yes O3 . C15 . C16 . 110.4(2) yes O3 . C15 . H151 . 109.2 no C16 . C15 . H151 . 109.2 no O3 . C15 . H152 . 109.2 no C16 . C15 . H152 . 109.2 no H151 . C15 . H152 . 109.5 no C15 . C16 . H161 . 109.5 no C15 . C16 . H162 . 109.5 no H161 . C16 . H162 . 109.5 no C15 . C16 . H163 . 109.5 no H161 . C16 . H163 . 109.5 no H162 . C16 . H163 . 109.5 no C12 . C17 . O4 . 123.5(2) yes C12 . C17 . O5 . 111.1(2) yes O4 . C17 . O5 . 125.3(2) yes C17 . O5 . C18 . 117.4(2) yes O5 . C18 . C19 . 109.1(2) yes O5 . C18 . H181 . 109.6 no C19 . C18 . H181 . 109.6 no O5 . C18 . H182 . 109.6 no C19 . C18 . H182 . 109.6 no H181 . C18 . H182 . 109.5 no C18 . C19 . H191 . 109.5 no C18 . C19 . H192 . 109.5 no H191 . C19 . H192 . 109.5 no C18 . C19 . H193 . 109.5 no H191 . C19 . H193 . 109.5 no H192 . C19 . H193 . 109.5 no C4 . C20 . O6 . 122.4(2) yes C4 . C20 . O7 . 112.5(2) yes O6 . C20 . O7 . 125.0(2) yes C20 . O7 . C21 . 117.4(2) yes O7 . C21 . C22 . 109.4(2) yes O7 . C21 . H211 . 109.5 no C22 . C21 . H211 . 109.5 no O7 . C21 . H212 . 109.5 no C22 . C21 . H212 . 109.5 no H211 . C21 . H212 . 109.5 no C21 . C22 . H221 . 109.5 no C21 . C22 . H222 . 109.5 no H221 . C22 . H222 . 109.5 no C21 . C22 . H223 . 109.5 no H221 . C22 . H223 . 109.5 no H222 . C22 . H223 . 109.5 no