# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_15 _database_code_depnum_ccdc_archive 'CCDC 922276' #TrackingRef 'CrystallographicData.cif' _cell_length_a 6.9174(2) _cell_length_b 9.4363(3) _cell_length_c 14.0634(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 917.99(5) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C8 H15 N1 O3 # Dc = 1.25 Fooo = 376.00 Mu = 7.90 M = 173.21 # Found Formula = C8 H15 N1 O3 # Dc = 1.25 FOOO = 376.00 Mu = 7.90 M = 173.21 _chemical_formula_sum 'C8 H15 N1 O3' _chemical_formula_moiety 'C8 H15 N1 O3' _chemical_compound_source . _chemical_formula_weight 173.21 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.030 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.790 # Sheldrick geometric approximatio 0.90 0.98 _exptl_absorpt_correction_type none _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 2686 _reflns_number_total 1119 _diffrn_reflns_av_R_equivalents 0.024 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 1119 # Theoretical number of reflections is about 1916 _diffrn_reflns_theta_min 5.646 _diffrn_reflns_theta_max 75.977 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 72.938 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _oxford_diffrn_Wilson_B_factor 1.99 _oxford_diffrn_Wilson_scale 0.01 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.17 _refine_diff_density_max 0.20 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>0.0\s(I) _refine_ls_number_reflns 2676 _refine_ls_number_restraints 0 _refine_ls_number_parameters 110 _oxford_refine_ls_R_factor_ref 0.0382 _refine_ls_wR_factor_ref 0.0864 _refine_ls_goodness_of_fit_ref 1.0023 _refine_ls_shift/su_max 0.0003045 _refine_ls_shift/su_mean 0.0000434 # The values computed with all filters except I/sigma _oxford_reflns_number_all 2676 _refine_ls_R_factor_all 0.0382 _refine_ls_wR_factor_all 0.0864 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2443 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_gt 0.0830 _refine_ls_abs_structure_Flack 0.1(2) _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.13P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.75490(14) 0.59752(10) 0.46326(7) 0.0225 1.0000 Uani . . . . . . C2 C 0.85622(18) 0.47252(13) 0.49131(9) 0.0182 1.0000 Uani . . . . . . C3 C 0.73431(19) 0.38464(14) 0.55971(10) 0.0199 1.0000 Uani . . . . . . O4 O 0.55689(13) 0.34908(10) 0.51334(8) 0.0250 1.0000 Uani . . . . . . C5 C 0.6935(2) 0.46321(16) 0.65021(10) 0.0247 1.0000 Uani . . . . . . C6 C 0.8043(2) 0.45141(19) 0.72669(11) 0.0328 1.0000 Uani . . . . . . C7 C 0.9780(2) 0.3551(2) 0.73495(11) 0.0344 1.0000 Uani . . . . . . C8 C 1.1608(2) 0.40859(17) 0.68484(10) 0.0277 1.0000 Uani . . . . . . N9 N 1.15394(16) 0.40122(12) 0.57980(8) 0.0201 1.0000 Uani . . . . . . C10 C 1.05330(19) 0.51940(13) 0.53118(10) 0.0184 1.0000 Uani . . . . . . C11 C 1.1787(2) 0.57342(14) 0.44978(10) 0.0228 1.0000 Uani . . . . . . O12 O 1.35434(14) 0.63557(10) 0.48289(8) 0.0278 1.0000 Uani . . . . . . H21 H 0.8818 0.4166 0.4347 0.0211 1.0000 Uiso R . . . . . H31 H 0.8061 0.2977 0.5758 0.0218 1.0000 Uiso R . . . . . H51 H 0.5857 0.5225 0.6506 0.0278 1.0000 Uiso R . . . . . H61 H 0.7769 0.5085 0.7798 0.0415 1.0000 Uiso R . . . . . H71 H 1.0105 0.3470 0.8029 0.0412 1.0000 Uiso R . . . . . H72 H 0.9409 0.2599 0.7100 0.0405 1.0000 Uiso R . . . . . H82 H 1.1867 0.5063 0.7028 0.0344 1.0000 Uiso R . . . . . H81 H 1.2715 0.3532 0.7048 0.0320 1.0000 Uiso R . . . . . H101 H 1.0331 0.5969 0.5757 0.0201 1.0000 Uiso R . . . . . H111 H 1.1038 0.6412 0.4105 0.0274 1.0000 Uiso R . . . . . H112 H 1.2122 0.4933 0.4085 0.0281 1.0000 Uiso R . . . . . H121 H 1.3292 0.7192 0.4977 0.0417 1.0000 Uiso R . . . . . H11 H 0.6373 0.5891 0.4679 0.0341 1.0000 Uiso R . . . . . H41 H 0.5823 0.2790 0.4761 0.0377 1.0000 Uiso R . . . . . H91 H 1.2786 0.4032 0.5612 0.0248 1.0000 Uiso 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 0.0142(4) 0.0196(4) 0.0336(5) 0.0020(4) -0.0023(4) 0.0008(4) C2 0.0138(6) 0.0169(5) 0.0240(6) -0.0017(5) -0.0006(5) 0.0006(5) C3 0.0123(6) 0.0172(6) 0.0302(6) -0.0004(5) -0.0002(5) -0.0007(5) O4 0.0123(4) 0.0198(4) 0.0430(6) -0.0063(4) -0.0012(4) -0.0011(4) C5 0.0178(6) 0.0260(6) 0.0303(7) -0.0014(6) 0.0073(5) -0.0017(6) C6 0.0270(7) 0.0441(9) 0.0275(7) 0.0000(6) 0.0084(6) 0.0004(7) C7 0.0305(8) 0.0469(9) 0.0258(7) 0.0073(6) 0.0012(6) 0.0016(8) C8 0.0210(6) 0.0344(7) 0.0277(7) 0.0005(6) -0.0050(6) 0.0011(7) N9 0.0132(5) 0.0204(5) 0.0268(5) -0.0001(4) 0.0004(4) 0.0004(5) C10 0.0125(5) 0.0168(5) 0.0259(6) -0.0032(5) 0.0006(5) -0.0010(5) C11 0.0167(6) 0.0217(6) 0.0299(7) 0.0013(5) 0.0015(5) -0.0013(5) O12 0.0143(4) 0.0184(4) 0.0508(6) -0.0005(4) 0.0045(5) -0.0015(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 8.9(3) 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 O1 . C2 . 1.4277(15) yes O1 . H11 . 0.820 no C2 . C3 . 1.5245(18) yes C2 . C10 . 1.5391(17) yes C2 . H21 . 0.972 no C3 . O4 . 1.4297(16) yes C3 . C5 . 1.4997(18) yes C3 . H31 . 0.986 no O4 . H41 . 0.862 no C5 . C6 . 1.325(2) yes C5 . H51 . 0.933 no C6 . C7 . 1.511(2) yes C6 . H61 . 0.940 no C7 . C8 . 1.533(2) yes C7 . H71 . 0.984 no C7 . H72 . 0.998 no C8 . N9 . 1.4797(17) yes C8 . H82 . 0.973 no C8 . H81 . 0.969 no N9 . C10 . 1.4819(17) yes N9 . H91 . 0.901 no C10 . C11 . 1.5241(18) yes C10 . H101 . 0.972 no C11 . O12 . 1.4271(16) yes C11 . H111 . 0.991 no C11 . H112 . 0.981 no O12 . H121 . 0.835 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 C2 . O1 . H11 . 112.7 no O1 . C2 . C3 . 110.62(10) yes O1 . C2 . C10 . 107.34(10) yes C3 . C2 . C10 . 114.61(11) yes O1 . C2 . H21 . 108.1 no C3 . C2 . H21 . 108.8 no C10 . C2 . H21 . 107.1 no C2 . C3 . O4 . 108.34(11) yes C2 . C3 . C5 . 111.76(11) yes O4 . C3 . C5 . 109.97(11) yes C2 . C3 . H31 . 108.6 no O4 . C3 . H31 . 110.0 no C5 . C3 . H31 . 108.1 no C3 . O4 . H41 . 106.4 no C3 . C5 . C6 . 122.58(14) yes C3 . C5 . H51 . 116.9 no C6 . C5 . H51 . 120.5 no C5 . C6 . C7 . 124.93(15) yes C5 . C6 . H61 . 118.7 no C7 . C6 . H61 . 116.4 no C6 . C7 . C8 . 114.98(14) yes C6 . C7 . H71 . 107.6 no C8 . C7 . H71 . 106.4 no C6 . C7 . H72 . 108.1 no C8 . C7 . H72 . 110.3 no H71 . C7 . H72 . 109.3 no C7 . C8 . N9 . 114.64(12) yes C7 . C8 . H82 . 110.2 no N9 . C8 . H82 . 108.0 no C7 . C8 . H81 . 110.0 no N9 . C8 . H81 . 106.8 no H82 . C8 . H81 . 106.9 no C8 . N9 . C10 . 116.13(11) yes C8 . N9 . H91 . 105.0 no C10 . N9 . H91 . 107.4 no C2 . C10 . N9 . 111.59(10) yes C2 . C10 . C11 . 109.07(11) yes N9 . C10 . C11 . 109.32(11) yes C2 . C10 . H101 . 108.9 no N9 . C10 . H101 . 109.7 no C11 . C10 . H101 . 108.3 no C10 . C11 . O12 . 112.15(11) yes C10 . C11 . H111 . 109.7 no O12 . C11 . H111 . 111.2 no C10 . C11 . H112 . 108.8 no O12 . C11 . H112 . 108.0 no H111 . C11 . H112 . 106.9 no C11 . O12 . H121 . 107.0 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C3 . H31 . O4 2_556 133.01(4) 0.986 2.549 3.301(2) yes O12 . H121 . O1 2_566 175.33(4) 0.835 1.886 2.719(2) yes O1 . H11 . O12 1_455 161.81(4) 0.820 2.017 2.808(2) yes O4 . H41 . N9 2_456 166.42(4) 0.862 1.938 2.783(2) yes N9 . H91 . O4 1_655 164.54(4) 0.901 2.103 2.981(2) yes data_29 _database_code_depnum_ccdc_archive 'CCDC 922277' #TrackingRef 'CrystallographicData.cif' _cell_length_a 9.05230(10) _cell_length_b 11.9795(2) _cell_length_c 22.5183(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2441.93(7) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C25 H36 N1 O6 # Dc = 1.21 Fooo = 968.00 Mu = 0.86 M = 446.56 # Found Formula = C25 H37 N1 O6 # Dc = 1.22 FOOO = 968.00 Mu = 0.86 M = 447.57 _chemical_formula_sum 'C25 H37 N1 O6' _chemical_formula_moiety 'C25 H37 N1 O6' _chemical_compound_source . _chemical_formula_weight 447.57 _cell_measurement_reflns_used 3020 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.230 _exptl_crystal_size_mid 0.290 _exptl_crystal_size_max 0.340 _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.086 # Sheldrick geometric approximatio 0.98 0.98 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.98 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 5399 _reflns_number_total 3145 _diffrn_reflns_av_R_equivalents 0.020 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 3145 # Theoretical number of reflections is about 4123 _diffrn_reflns_theta_min 5.145 _diffrn_reflns_theta_max 27.475 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.651 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _reflns_limit_h_min 0 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 29 _oxford_diffrn_Wilson_B_factor 2.53 _oxford_diffrn_Wilson_scale 2.29 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.15 _refine_diff_density_max 0.13 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 2332 _refine_ls_number_restraints 0 _refine_ls_number_parameters 289 _oxford_refine_ls_R_factor_ref 0.0322 _refine_ls_wR_factor_ref 0.0678 _refine_ls_goodness_of_fit_ref 0.9306 _refine_ls_shift/su_max 0.0004097 _refine_ls_shift/su_mean 0.0000387 # The values computed from all data _oxford_reflns_number_all 2332 _refine_ls_R_factor_all 0.0322 _refine_ls_wR_factor_all 0.0678 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2144 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_gt 0.0635 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 22.4 36.0 21.9 9.71 2.55 ; # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.57188(15) 0.46607(10) 0.65146(5) 0.0254 1.0000 Uani . . . . . . C2 C 0.6170(2) 0.57094(15) 0.67674(8) 0.0232 1.0000 Uani . . . . . . C3 C 0.5001(2) 0.65569(16) 0.65536(8) 0.0266 1.0000 Uani . . . . . . O4 O 0.38349(15) 0.58476(11) 0.63363(6) 0.0302 1.0000 Uani . . . . . . C5 C 0.4521(2) 0.48734(16) 0.61138(8) 0.0258 1.0000 Uani . . . . . . C6 C 0.3433(2) 0.39212(18) 0.61519(9) 0.0334 1.0000 Uani . . . . . . C7 C 0.5096(2) 0.50559(18) 0.54856(8) 0.0328 1.0000 Uani . . . . . . C8 C 0.4380(2) 0.72873(18) 0.70308(9) 0.0364 1.0000 Uani . . . . . . C9 C 0.5040(3) 0.81574(19) 0.72742(9) 0.0384 1.0000 Uani . . . . . . C10 C 0.6536(2) 0.86185(17) 0.71234(9) 0.0351 1.0000 Uani . . . . . . C11 C 0.7794(2) 0.77542(17) 0.71431(8) 0.0295 1.0000 Uani . . . . . . N12 N 0.80096(18) 0.71814(13) 0.65679(7) 0.0235 1.0000 Uani . . . . . . C13 C 0.7757(2) 0.59712(14) 0.65695(8) 0.0213 1.0000 Uani . . . . . . C14 C 0.8905(2) 0.52703(16) 0.69147(8) 0.0252 1.0000 Uani . . . . . . O15 O 0.87992(18) 0.54243(12) 0.75393(6) 0.0371 1.0000 Uani . . . . . . C16 C 0.8767(2) 0.40227(16) 0.67870(8) 0.0254 1.0000 Uani . . . . . . O17 O 0.89264(16) 0.38024(10) 0.62154(6) 0.0286 1.0000 Uani . . . . . . C18 C 0.8800(3) 0.26396(16) 0.59853(9) 0.0331 1.0000 Uani . . . . . . C19 C 1.0086(3) 0.19585(18) 0.62158(12) 0.0454 1.0000 Uani . . . . . . C20 C 0.7324(3) 0.2146(2) 0.61483(13) 0.0498 1.0000 Uani . . . . . . C21 C 0.8921(4) 0.2824(2) 0.53220(10) 0.0585 1.0000 Uani . . . . . . O22 O 0.85776(17) 0.33569(11) 0.71831(6) 0.0346 1.0000 Uani . . . . . . C23 C 0.9349(2) 0.75486(15) 0.62463(9) 0.0269 1.0000 Uani . . . . . . C24 C 0.9502(2) 0.69374(15) 0.56594(8) 0.0244 1.0000 Uani . . . . . . C25 C 1.0698(2) 0.62362(16) 0.55545(8) 0.0282 1.0000 Uani . . . . . . C26 C 1.0794(2) 0.56199(17) 0.50339(8) 0.0303 1.0000 Uani . . . . . . C27 C 0.9692(2) 0.56926(17) 0.46079(8) 0.0296 1.0000 Uani . . . . . . O28 O 0.98667(17) 0.50085(14) 0.41232(6) 0.0423 1.0000 Uani . . . . . . C29 C 0.8634(3) 0.4854(2) 0.37420(10) 0.0465 1.0000 Uani . . . . . . C30 C 0.8525(2) 0.64210(17) 0.46920(8) 0.0300 1.0000 Uani . . . . . . C31 C 0.8440(2) 0.70335(16) 0.52167(8) 0.0282 1.0000 Uani . . . . . . C32 C 0.9306(3) 0.88154(16) 0.61423(10) 0.0350 1.0000 Uani . . . . . . H21 H 0.6114 0.5648 0.7205 0.0262 1.0000 Uiso R . . . . . H31 H 0.5427 0.7028 0.6236 0.0308 1.0000 Uiso R . . . . . H62 H 0.2617 0.4085 0.5884 0.0481 1.0000 Uiso R . . . . . H63 H 0.3938 0.3241 0.6029 0.0483 1.0000 Uiso R . . . . . H61 H 0.3075 0.3870 0.6555 0.0491 1.0000 Uiso R . . . . . H73 H 0.4241 0.5191 0.5231 0.0483 1.0000 Uiso R . . . . . H71 H 0.5615 0.4399 0.5358 0.0479 1.0000 Uiso R . . . . . H72 H 0.5739 0.5700 0.5479 0.0478 1.0000 Uiso R . . . . . H81 H 0.3449 0.7071 0.7172 0.0433 1.0000 Uiso R . . . . . H91 H 0.4518 0.8529 0.7587 0.0462 1.0000 Uiso R . . . . . H102 H 0.6496 0.8936 0.6706 0.0408 1.0000 Uiso R . . . . . H101 H 0.6775 0.9218 0.7404 0.0407 1.0000 Uiso R . . . . . H112 H 0.7534 0.7181 0.7446 0.0336 1.0000 Uiso R . . . . . H111 H 0.8734 0.8129 0.7246 0.0354 1.0000 Uiso R . . . . . H131 H 0.7837 0.5725 0.6154 0.0236 1.0000 Uiso R . . . . . H141 H 0.9909 0.5524 0.6785 0.0297 1.0000 Uiso R . . . . . H191 H 1.0070 0.1255 0.6009 0.0659 1.0000 Uiso R . . . . . H192 H 1.0987 0.2343 0.6122 0.0665 1.0000 Uiso R . . . . . H193 H 0.9989 0.1842 0.6640 0.0660 1.0000 Uiso R . . . . . H203 H 0.7193 0.1419 0.5945 0.0720 1.0000 Uiso R . . . . . H202 H 0.6531 0.2666 0.6041 0.0732 1.0000 Uiso R . . . . . H201 H 0.7302 0.2009 0.6573 0.0724 1.0000 Uiso R . . . . . H211 H 0.8837 0.2100 0.5126 0.0854 1.0000 Uiso R . . . . . H212 H 0.8168 0.3323 0.5190 0.0862 1.0000 Uiso R . . . . . H213 H 0.9888 0.3151 0.5240 0.0860 1.0000 Uiso R . . . . . H231 H 1.0244 0.7386 0.6483 0.0306 1.0000 Uiso R . . . . . H251 H 1.1443 0.6160 0.5846 0.0340 1.0000 Uiso R . . . . . H261 H 1.1604 0.5137 0.4968 0.0367 1.0000 Uiso R . . . . . H293 H 0.8891 0.4288 0.3441 0.0703 1.0000 Uiso R . . . . . H292 H 0.8351 0.5574 0.3535 0.0694 1.0000 Uiso R . . . . . H291 H 0.7773 0.4581 0.3985 0.0698 1.0000 Uiso R . . . . . H301 H 0.7791 0.6487 0.4404 0.0351 1.0000 Uiso R . . . . . H311 H 0.7643 0.7521 0.5274 0.0337 1.0000 Uiso R . . . . . H321 H 1.0191 0.9013 0.5916 0.0511 1.0000 Uiso R . . . . . H322 H 0.8423 0.9007 0.5919 0.0511 1.0000 Uiso R . . . . . H323 H 0.9299 0.9213 0.6531 0.0500 1.0000 Uiso R . . . . . H151 H 0.8674 0.4784 0.7688 0.0555 1.0000 Uiso 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 0.0264(7) 0.0226(6) 0.0271(6) 0.0023(5) -0.0064(6) -0.0033(6) C2 0.0256(9) 0.0259(9) 0.0180(8) -0.0024(7) -0.0015(8) -0.0005(8) C3 0.0246(9) 0.0282(10) 0.0270(9) -0.0040(8) -0.0019(8) 0.0010(8) O4 0.0215(6) 0.0332(7) 0.0358(7) -0.0038(6) -0.0039(6) 0.0008(6) C5 0.0217(9) 0.0309(10) 0.0246(9) 0.0008(8) -0.0044(8) 0.0000(9) C6 0.0304(11) 0.0379(12) 0.0319(11) -0.0003(9) -0.0052(9) -0.0071(9) C7 0.0333(11) 0.0384(11) 0.0267(10) -0.0015(8) -0.0038(9) -0.0051(10) C8 0.0293(10) 0.0398(11) 0.0400(11) -0.0067(10) 0.0025(10) 0.0058(10) C9 0.0413(12) 0.0376(12) 0.0365(11) -0.0095(10) 0.0038(10) 0.0109(11) C10 0.0466(12) 0.0273(10) 0.0315(10) -0.0084(9) -0.0005(10) 0.0052(10) C11 0.0358(11) 0.0275(10) 0.0251(9) -0.0043(9) -0.0048(9) -0.0009(9) N12 0.0267(8) 0.0188(7) 0.0251(8) -0.0032(7) -0.0013(7) -0.0009(7) C13 0.0243(9) 0.0189(9) 0.0207(8) -0.0026(7) -0.0030(8) -0.0014(8) C14 0.0256(10) 0.0263(9) 0.0238(9) -0.0015(8) -0.0043(8) -0.0001(9) O15 0.0509(9) 0.0357(8) 0.0247(7) -0.0009(6) -0.0119(7) 0.0046(7) C16 0.0211(9) 0.0247(10) 0.0304(10) 0.0037(8) -0.0024(8) 0.0008(8) O17 0.0353(7) 0.0201(6) 0.0305(7) -0.0011(5) 0.0010(6) 0.0017(6) C18 0.0369(11) 0.0206(9) 0.0418(11) -0.0076(8) -0.0017(10) 0.002(1) C19 0.0384(12) 0.0239(11) 0.0739(16) -0.0065(11) -0.0030(13) 0.0054(10) C20 0.0373(12) 0.0361(12) 0.0761(18) -0.0155(13) -0.0037(13) -0.0080(11) C21 0.091(2) 0.0393(13) 0.0454(13) -0.0154(11) 0.0022(15) 0.0069(15) O22 0.0378(8) 0.0306(7) 0.0354(8) 0.0095(6) -0.0001(7) -0.0005(6) C23 0.0230(9) 0.0246(9) 0.0331(10) 0.0019(8) -0.0048(9) -0.0037(8) C24 0.0228(9) 0.0213(9) 0.0292(9) 0.0057(8) 0.0002(8) -0.0039(8) C25 0.0205(9) 0.0317(10) 0.0323(10) 0.0069(8) -0.0005(8) -0.0020(9) C26 0.0212(10) 0.0343(10) 0.0352(10) 0.0049(9) 0.0048(8) 0.0025(9) C27 0.0284(10) 0.0331(10) 0.0274(9) 0.0032(8) 0.0051(8) -0.0036(9) O28 0.0389(9) 0.0549(10) 0.0331(7) -0.0101(7) 0.0041(7) 0.0044(8) C29 0.0473(13) 0.0551(14) 0.0370(11) -0.0114(11) -0.0022(11) -0.0084(12) C30 0.0278(10) 0.0365(10) 0.0258(9) 0.0060(9) -0.0025(8) 0.0004(9) C31 0.0238(9) 0.0283(10) 0.0327(10) 0.0045(8) -0.0008(8) 0.0034(8) C32 0.0369(11) 0.0260(10) 0.0420(11) -0.0001(9) 0.0005(10) -0.0070(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.6618(15) 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 O1 . C2 . 1.439(2) yes O1 . C5 . 1.434(2) yes C2 . C3 . 1.544(3) yes C2 . C13 . 1.536(3) yes C2 . H21 . 0.990 no C3 . O4 . 1.441(2) yes C3 . C8 . 1.496(3) yes C3 . H31 . 0.989 no O4 . C5 . 1.414(2) yes C5 . C6 . 1.509(3) yes C5 . C7 . 1.523(3) yes C6 . H62 . 0.973 no C6 . H63 . 0.975 no C6 . H61 . 0.965 no C7 . H73 . 0.977 no C7 . H71 . 0.960 no C7 . H72 . 0.966 no C8 . C9 . 1.321(3) yes C8 . H81 . 0.937 no C9 . C10 . 1.502(3) yes C9 . H91 . 0.959 no C10 . C11 . 1.540(3) yes C10 . H102 . 1.014 no C10 . H101 . 0.981 no C11 . N12 . 1.479(2) yes C11 . H112 . 0.996 no C11 . H111 . 0.989 no N12 . C13 . 1.468(2) yes N12 . C23 . 1.480(2) yes C13 . C14 . 1.546(3) yes C13 . H131 . 0.984 no C14 . O15 . 1.422(2) yes C14 . C16 . 1.527(3) yes C14 . H141 . 1.002 no O15 . H151 . 0.845 no C16 . O17 . 1.322(2) yes C16 . O22 . 1.209(2) yes O17 . C18 . 1.491(2) yes C18 . C19 . 1.514(3) yes C18 . C20 . 1.506(3) yes C18 . C21 . 1.514(3) yes C19 . H191 . 0.964 no C19 . H192 . 0.961 no C19 . H193 . 0.969 no C20 . H203 . 0.991 no C20 . H202 . 0.980 no C20 . H201 . 0.970 no C21 . H211 . 0.975 no C21 . H212 . 0.954 no C21 . H213 . 0.978 no C23 . C24 . 1.517(3) yes C23 . C32 . 1.536(3) yes C23 . H231 . 0.989 no C24 . C25 . 1.391(3) yes C24 . C31 . 1.390(3) yes C25 . C26 . 1.388(3) yes C25 . H251 . 0.946 no C26 . C27 . 1.387(3) yes C26 . H261 . 0.946 no C27 . O28 . 1.374(2) yes C27 . C30 . 1.383(3) yes O28 . C29 . 1.420(3) yes C29 . H293 . 0.987 no C29 . H292 . 1.012 no C29 . H291 . 1.006 no C30 . C31 . 1.393(3) yes C30 . H301 . 0.932 no C31 . H311 . 0.937 no C32 . H321 . 0.979 no C32 . H322 . 0.971 no C32 . H323 . 0.996 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 C2 . O1 . C5 . 107.99(13) yes O1 . C2 . C3 . 104.84(14) yes O1 . C2 . C13 . 109.22(14) yes C3 . C2 . C13 . 114.59(15) yes O1 . C2 . H21 . 108.4 no C3 . C2 . H21 . 108.9 no C13 . C2 . H21 . 110.6 no C2 . C3 . O4 . 102.73(14) yes C2 . C3 . C8 . 114.75(16) yes O4 . C3 . C8 . 108.26(16) yes C2 . C3 . H31 . 109.4 no O4 . C3 . H31 . 112.1 no C8 . C3 . H31 . 109.4 no C3 . O4 . C5 . 106.59(14) yes O1 . C5 . O4 . 104.82(14) yes O1 . C5 . C6 . 108.87(15) yes O4 . C5 . C6 . 108.50(16) yes O1 . C5 . C7 . 110.56(15) yes O4 . C5 . C7 . 111.16(16) yes C6 . C5 . C7 . 112.61(16) yes C5 . C6 . H62 . 107.9 no C5 . C6 . H63 . 108.0 no H62 . C6 . H63 . 110.4 no C5 . C6 . H61 . 108.7 no H62 . C6 . H61 . 109.9 no H63 . C6 . H61 . 111.8 no C5 . C7 . H73 . 107.3 no C5 . C7 . H71 . 109.1 no H73 . C7 . H71 . 110.4 no C5 . C7 . H72 . 109.6 no H73 . C7 . H72 . 109.6 no H71 . C7 . H72 . 110.8 no C3 . C8 . C9 . 126.1(2) yes C3 . C8 . H81 . 114.9 no C9 . C8 . H81 . 118.9 no C8 . C9 . C10 . 127.2(2) yes C8 . C9 . H91 . 116.7 no C10 . C9 . H91 . 116.1 no C9 . C10 . C11 . 114.41(17) yes C9 . C10 . H102 . 108.3 no C11 . C10 . H102 . 107.8 no C9 . C10 . H101 . 108.8 no C11 . C10 . H101 . 108.1 no H102 . C10 . H101 . 109.3 no C10 . C11 . N12 . 112.60(15) yes C10 . C11 . H112 . 108.0 no N12 . C11 . H112 . 108.1 no C10 . C11 . H111 . 109.8 no N12 . C11 . H111 . 107.6 no H112 . C11 . H111 . 110.8 no C11 . N12 . C13 . 115.82(15) yes C11 . N12 . C23 . 113.50(15) yes C13 . N12 . C23 . 115.01(15) yes C2 . C13 . N12 . 110.38(15) yes C2 . C13 . C14 . 111.83(14) yes N12 . C13 . C14 . 115.65(15) yes C2 . C13 . H131 . 106.5 no N12 . C13 . H131 . 106.4 no C14 . C13 . H131 . 105.4 no C13 . C14 . O15 . 112.44(16) yes C13 . C14 . C16 . 112.45(15) yes O15 . C14 . C16 . 107.92(15) yes C13 . C14 . H141 . 107.4 no O15 . C14 . H141 . 108.1 no C16 . C14 . H141 . 108.4 no C14 . O15 . H151 . 106.5 no C14 . C16 . O17 . 111.69(15) yes C14 . C16 . O22 . 121.24(16) yes O17 . C16 . O22 . 127.04(17) yes C16 . O17 . C18 . 121.11(15) yes O17 . C18 . C19 . 108.98(16) yes O17 . C18 . C20 . 110.50(17) yes C19 . C18 . C20 . 112.78(18) yes O17 . C18 . C21 . 101.62(17) yes C19 . C18 . C21 . 111.2(2) yes C20 . C18 . C21 . 111.2(2) yes C18 . C19 . H191 . 107.1 no C18 . C19 . H192 . 108.6 no H191 . C19 . H192 . 109.0 no C18 . C19 . H193 . 110.2 no H191 . C19 . H193 . 110.4 no H192 . C19 . H193 . 111.4 no C18 . C20 . H203 . 109.8 no C18 . C20 . H202 . 109.9 no H203 . C20 . H202 . 110.9 no C18 . C20 . H201 . 109.0 no H203 . C20 . H201 . 107.6 no H202 . C20 . H201 . 109.6 no C18 . C21 . H211 . 108.1 no C18 . C21 . H212 . 110.3 no H211 . C21 . H212 . 111.2 no C18 . C21 . H213 . 108.1 no H211 . C21 . H213 . 109.9 no H212 . C21 . H213 . 109.2 no N12 . C23 . C24 . 110.95(15) yes N12 . C23 . C32 . 110.31(17) yes C24 . C23 . C32 . 110.26(16) yes N12 . C23 . H231 . 110.4 no C24 . C23 . H231 . 107.4 no C32 . C23 . H231 . 107.4 no C23 . C24 . C25 . 120.69(17) yes C23 . C24 . C31 . 121.45(17) yes C25 . C24 . C31 . 117.84(18) yes C24 . C25 . C26 . 120.88(18) yes C24 . C25 . H251 . 119.7 no C26 . C25 . H251 . 119.4 no C25 . C26 . C27 . 120.40(18) yes C25 . C26 . H261 . 120.3 no C27 . C26 . H261 . 119.3 no C26 . C27 . O28 . 115.40(18) yes C26 . C27 . C30 . 119.63(18) yes O28 . C27 . C30 . 124.97(18) yes C27 . O28 . C29 . 117.86(17) yes O28 . C29 . H293 . 108.7 no O28 . C29 . H292 . 111.4 no H293 . C29 . H292 . 109.1 no O28 . C29 . H291 . 108.8 no H293 . C29 . H291 . 109.4 no H292 . C29 . H291 . 109.3 no C27 . C30 . C31 . 119.38(18) yes C27 . C30 . H301 . 120.1 no C31 . C30 . H301 . 120.5 no C30 . C31 . C24 . 121.77(18) yes C30 . C31 . H311 . 119.2 no C24 . C31 . H311 . 119.0 no C23 . C32 . H321 . 107.3 no C23 . C32 . H322 . 109.5 no H321 . C32 . H322 . 110.3 no C23 . C32 . H323 . 109.8 no H321 . C32 . H323 . 110.3 no H322 . C32 . H323 . 109.7 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C9 . H91 . O1 3_656 155.49(6) 0.959 2.444 3.340(3) yes C11 . H112 . O15 . 123.43(6) 0.996 2.405 3.068(3) yes C25 . H251 . O4 1_655 162.62(5) 0.946 2.459 3.373(3) yes O15 . H151 . O22 . 122.81(5) 0.845 2.055 2.611(3) yes