# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '8643_web_deposit_cif_file_0_MalekNechab_1323785453.sm1114.cif' _audit_creation_date 11-12-07 _audit_creation_method CRYSTALS_ver_14.11 _oxford_structure_analysis_title 'sm1114 in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _publ_contact_author_name 'Malek Nechab' _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Nowhere, Nowhere, NO1 4T, UK. ; _publ_section_title # Title of paper - generally just the systematic or trivial name ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address _publ_author_footnote # Author 1 # Author 2 'S. Mondal' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'M. Nechab' ; ? # Address 2 ; ; ? # Footnote 2 ; 'D. Campolo' '' '' 'N. Vanthuyne' '' '' 'M. P. Bertrand' '' '' _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_contact_author_email malek.nechab@univ-provence.fr data_1 _database_code_depnum_ccdc_archive 'CCDC 858572' #TrackingRef '8643_web_deposit_cif_file_0_MalekNechab_1323785453.sm1114.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; No of Reflections processed = 2544 No of Friedel Pairs found = 1023 No of Friedel Pairs used = 1023 No of Unpaired Reflections = 4 No of Centric Reflections = 494 Flack parameter obtained from original refinement Hooft parameter obtained with Flack x set to zero Reflections only used if /Fo+ - Fo-/ < 99999.00 * /Fc+ - Fc-/ Friedif = 29.79 Acta A63, (2007), 257-265 Flack & Shmueli (2007) recommend a value >200 for general structures and >80 for enantiopure crystals Flack Parameter & su 0.0291 0.1838 Hooft Parameter & su 0.0543 0.0950 Ton G & su 0.8914 0.1900 No of reflections for which delta(Fo) has same sign as delta(Fc) Same sign Opposite sign 552 471 For an enantiopure material, there are 2 choices, P2 P2(correct) 1.0000 i.e. 0.100000E+01 If 50:50 twinning is possible, there are 3 choices, P3 P3(correct) 1.0000 i.e. 0.999980E+00 P3(rac-twin) 0.0000 i.e. 0.195247E-04 P3(inverse) 0.0000 i.e. 0.353620E-21 G 0.8914 G S.U. 0.1900 FLEQ 0.0543 FLEQ S.U. 0.0950 i.e. 0.949904E-01 ; #--------------------------------------------------------------- _cell_length_a 5.89431(12) _cell_length_b 8.01643(17) _cell_length_c 30.0923(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1421.90(5) _cell_measurement_reflns_used 6983 _cell_measurement_theta_min 5.5139 _cell_measurement_theta_max 67.3357 _cell_oxdiff_length_a 5.8936(3) _cell_oxdiff_length_b 8.0176(4) _cell_oxdiff_length_c 30.0915(12) _cell_oxdiff_angle_alpha 90.018(3) _cell_oxdiff_angle_beta 90.009(3) _cell_oxdiff_angle_gamma 90.015(4) _cell_oxdiff_volume 1421.90(10) _cell_oxdiff_measurement_reflns_used 6984 _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,z+1/2 x+1/2,-y+1/2,-z -x,y+1/2,-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' 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' 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' _cell_formula_units_Z 4 _chemical_formula_sum 'C18 H17 N O3' _chemical_formula_moiety 'C18 H17 N O3' _chemical_compound_source ? _chemical_formula_weight 295.33 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.200 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_max 0.300 _exptl_absorpt_correction_T_min 0.70399 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.764 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini' _diffrn_detector_area_resol_mean 16.0143 _diffrn_measurement_device Area _diffrn_radiation_wavelength 1.54180 #montpellier_reflns_maxres is minimum d (highest resolution) #where <= 2.0 #(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999) _montpellier_reflns_maxres 0.83 _montpellier_reflns_completeness_maxres 99.68 _montpellier_reflns_redundancy_maxres 8.39 #montpellier_diffrn_reflns_class_completeness_shell is completeness in shell #montpellier_diffrn_class_reflns_cumul_completeness is cumulative #completeness to resolution of shell #Note: completeness percentage takes into account the fact whether #group is centrosymmetric or not loop_ _montpellier_diffrn_reflns_class_number _montpellier_diffrn_reflns_class_d_res_high _montpellier_diffrn_reflns_class_d_res_low _montpellier_diffrn_reflns_class_redundancy _montpellier_diffrn_reflns_class_av_I/uI _diffrn_reflns_class_av_R_eq _montpellier_diffrn_reflns_class_completeness_shell _montpellier_diffrn_reflns_class_cumul_completeness 0 100.0 1.91 6.4 40.29 0.050 98.1 98.09 1 1.91 1.49 6.0 25.03 0.059 100.0 99.04 2 1.49 1.29 9.9 37.48 0.059 99.4 99.14 3 1.29 1.16 10.8 47.45 0.038 100.0 99.35 4 1.16 1.07 9.8 42.16 0.053 100.0 99.48 5 1.07 1.00 9.9 36.00 0.069 100.0 99.57 6 1.00 0.95 8.9 30.10 0.076 100.0 99.63 7 0.95 0.91 8.6 27.81 0.066 100.0 99.68 8 0.90 0.87 7.8 23.87 0.063 100.0 99.71 9 0.87 0.83 5.8 25.57 0.061 99.4 99.68 #End reflection statistics _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _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_orient_matrix_UB_11 0.2404766000 _diffrn_orient_matrix_UB_12 -0.0745119000 _diffrn_orient_matrix_UB_13 0.0028175000 _diffrn_orient_matrix_UB_21 0.0189325000 _diffrn_orient_matrix_UB_22 0.0058309000 _diffrn_orient_matrix_UB_23 -0.0510387000 _diffrn_orient_matrix_UB_31 0.1006769000 _diffrn_orient_matrix_UB_32 0.1770138000 _diffrn_orient_matrix_UB_33 0.0028856000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -103.00 -36.00 1.0000 1.6500 omega____ theta____ kappa____ phi______ frames - -33.7678 -179.0000 -150.0000 67 #__ type_ start__ end____ width___ exp.time_ 2 omega -80.00 -43.00 1.0000 1.6500 omega____ theta____ kappa____ phi______ frames - -33.7678 -179.0000 -60.0000 37 #__ type_ start__ end____ width___ exp.time_ 3 omega -102.00 -32.00 1.0000 1.6500 omega____ theta____ kappa____ phi______ frames - -33.7678 179.0000 120.0000 70 #__ type_ start__ end____ width___ exp.time_ 4 omega 11.00 37.00 1.0000 1.6500 omega____ theta____ kappa____ phi______ frames - 33.7678 77.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 5 omega 60.00 96.00 1.0000 1.6500 omega____ theta____ kappa____ phi______ frames - 33.7678 77.0000 -120.0000 36 #__ type_ start__ end____ width___ exp.time_ 6 omega 32.00 88.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -25.0000 -90.0000 56 #__ type_ start__ end____ width___ exp.time_ 7 omega 34.00 60.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -38.0000 90.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega 74.00 99.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 38.0000 -30.0000 25 #__ type_ start__ end____ width___ exp.time_ 9 omega 57.00 109.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 179.0000 -60.0000 52 #__ type_ start__ end____ width___ exp.time_ 10 omega 32.00 90.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -25.0000 150.0000 58 #__ type_ start__ end____ width___ exp.time_ 11 omega 113.00 142.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 179.0000 -60.0000 29 #__ type_ start__ end____ width___ exp.time_ 12 omega 102.00 127.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 112.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 13 omega 142.00 169.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 112.0000 0.0000 27 #__ type_ start__ end____ width___ exp.time_ 14 omega 71.00 170.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 77.0000 -120.0000 99 #__ type_ start__ end____ width___ exp.time_ 15 omega 31.00 65.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -38.0000 120.0000 34 #__ type_ start__ end____ width___ exp.time_ 16 omega 113.00 162.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 51.0000 -60.0000 49 #__ type_ start__ end____ width___ exp.time_ 17 omega 76.00 112.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -112.0000 -120.0000 36 #__ type_ start__ end____ width___ exp.time_ 18 omega 48.00 74.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -38.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 19 omega 116.00 171.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 38.0000 -30.0000 55 #__ type_ start__ end____ width___ exp.time_ 20 omega -110.00 -32.00 1.0000 1.6500 omega____ theta____ kappa____ phi______ frames - -33.7678 179.0000 0.0000 78 #__ type_ start__ end____ width___ exp.time_ 21 omega 13.00 103.00 1.0000 1.6500 omega____ theta____ kappa____ phi______ frames - 33.7678 57.0000 -150.0000 90 #__ type_ start__ end____ width___ exp.time_ 22 omega 13.00 103.00 1.0000 1.6500 omega____ theta____ kappa____ phi______ frames - 33.7678 57.0000 0.0000 90 #__ type_ start__ end____ width___ exp.time_ 23 omega 13.00 103.00 1.0000 1.6500 omega____ theta____ kappa____ phi______ frames - 33.7678 57.0000 120.0000 90 #__ type_ start__ end____ width___ exp.time_ 24 omega 70.00 140.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 77.0000 -150.0000 70 #__ type_ start__ end____ width___ exp.time_ 25 omega 28.00 138.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -92.0000 -60.0000 110 #__ type_ start__ end____ width___ exp.time_ 26 omega 70.00 170.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 77.0000 -180.0000 100 #__ type_ start__ end____ width___ exp.time_ 27 omega 77.00 167.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 64.0000 -30.0000 90 #__ type_ start__ end____ width___ exp.time_ 28 omega 74.00 172.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 38.0000 90.0000 98 #__ type_ start__ end____ width___ exp.time_ 29 omega 30.00 130.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -77.0000 60.0000 100 #__ type_ start__ end____ width___ exp.time_ 30 omega 70.00 170.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 77.0000 120.0000 100 #__ type_ start__ end____ width___ exp.time_ 31 omega 78.00 170.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 51.0000 30.0000 92 ; _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 150 _diffrn_reflns_number 12903 _reflns_number_total 2544 _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_av_sigmaI/netI 0.0917 # Number of reflections without Friedels Law is 2544 # Number of reflections with Friedels Law is 1521 # Theoretical number of reflections is about 1280 _diffrn_reflns_theta_min 5.711 _diffrn_reflns_theta_max 67.446 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 67.446 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 35 _oxford_diffrn_Wilson_B_factor 2.43 _oxford_diffrn_Wilson_scale 0.02 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.23 _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 2544 _refine_ls_number_restraints 0 _refine_ls_number_parameters 200 _oxford_refine_ls_R_factor_ref 0.0324 _refine_ls_wR_factor_ref 0.0809 _refine_ls_goodness_of_fit_ref 0.9910 _refine_ls_shift/su_max 0.0005291 _refine_ls_shift/su_mean 0.0000685 # The values computed from all data _oxford_reflns_number_all 2544 _refine_ls_R_factor_all 0.0324 _refine_ls_wR_factor_all 0.0809 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2488 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_gt 0.0803 _refine_ls_abs_structure_Flack 0.03(18) _refine_ls_abs_structure_details 'Flack (1983), 1023 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 none # none, 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^) + ( 0.06P)^2^ + 0.15P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2006). Gemini User Manual. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 0.57079(19) 0.27156(13) 0.32460(4) 0.0313 1.0000 Uani . . . . . . C2 C 0.7415(2) 0.37802(18) 0.33214(4) 0.0231 1.0000 Uani . . . . . . O3 O 0.92951(18) 0.33826(14) 0.34267(4) 0.0342 1.0000 Uani . . . . . . C4 C 0.6569(2) 0.55793(16) 0.32567(4) 0.0226 1.0000 Uani . . . . . . N5 N 0.8362(2) 0.67638(14) 0.33672(4) 0.0234 1.0000 Uani . . . . . . C6 C 0.9428(2) 0.74216(18) 0.30106(5) 0.0248 1.0000 Uani . . . . . . O7 O 1.09948(17) 0.84278(13) 0.30326(4) 0.0306 1.0000 Uani . . . . . . C8 C 0.8356(3) 0.6718(2) 0.25965(5) 0.0304 1.0000 Uani . . . . . . C9 C 0.6135(3) 0.59413(19) 0.27585(5) 0.0273 1.0000 Uani . . . . . . H91 H 0.4900 0.6742 0.2742 0.0327 1.0000 Uiso R . . . . . H92 H 0.5765 0.4950 0.2599 0.0340 1.0000 Uiso R . . . . . H81 H 0.8190 0.7550 0.2375 0.0365 1.0000 Uiso R . . . . . H82 H 0.9336 0.5889 0.2475 0.0361 1.0000 Uiso R . . . . . C10 C 0.8912(2) 0.72408(18) 0.38228(4) 0.0236 1.0000 Uani . . . . . . C11 C 0.7442(2) 0.63786(16) 0.41634(4) 0.0206 1.0000 Uani . . . . . . C12 C 0.5285(2) 0.57182(16) 0.40400(4) 0.0204 1.0000 Uani . . . . . . C13 C 0.4539(2) 0.58934(18) 0.35618(4) 0.0220 1.0000 Uani . . . . . . H131 H 0.4009 0.7026 0.3503 0.0253 1.0000 Uiso R . . . . . H132 H 0.3314 0.5151 0.3493 0.0258 1.0000 Uiso R . . . . . C14 C 0.3986(2) 0.49093(16) 0.43509(4) 0.0220 1.0000 Uani . . . . . . C15 C 0.4733(2) 0.47440(17) 0.47975(5) 0.0223 1.0000 Uani . . . . . . C16 C 0.6870(2) 0.54283(17) 0.49217(5) 0.0227 1.0000 Uani . . . . . . C17 C 0.8187(2) 0.62420(17) 0.45939(5) 0.0224 1.0000 Uani . . . . . . H171 H 0.9592 0.6675 0.4675 0.0258 1.0000 Uiso R . . . . . C18 C 0.7647(3) 0.52196(19) 0.53674(5) 0.0272 1.0000 Uani . . . . . . C19 C 0.6376(3) 0.43359(19) 0.56676(5) 0.0307 1.0000 Uani . . . . . . C20 C 0.4263(3) 0.3649(2) 0.55423(5) 0.0302 1.0000 Uani . . . . . . C21 C 0.3445(3) 0.38600(18) 0.51203(5) 0.0262 1.0000 Uani . . . . . . H211 H 0.2068 0.3432 0.5038 0.0317 1.0000 Uiso R . . . . . H201 H 0.3409 0.3007 0.5756 0.0345 1.0000 Uiso R . . . . . H191 H 0.6893 0.4186 0.5952 0.0361 1.0000 Uiso R . . . . . H181 H 0.9067 0.5683 0.5447 0.0312 1.0000 Uiso R . . . . . H141 H 0.2582 0.4444 0.4264 0.0255 1.0000 Uiso R . . . . . H101 H 0.8700 0.8463 0.3849 0.0279 1.0000 Uiso R . . . . . H102 H 1.0477 0.6955 0.3882 0.0276 1.0000 Uiso R . . . . . C22 C 0.6186(3) 0.09723(19) 0.33158(5) 0.0360 1.0000 Uani . . . . . . H221 H 0.4890 0.0345 0.3213 0.0542 1.0000 Uiso R . . . . . H222 H 0.6315 0.0775 0.3632 0.0532 1.0000 Uiso R . . . . . H223 H 0.7541 0.0645 0.3165 0.0544 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 0.0351(6) 0.0203(5) 0.0385(6) -0.0008(4) -0.0060(5) -0.0012(4) C2 0.0255(7) 0.0263(7) 0.0174(6) -0.0021(5) 0.0022(5) 0.0011(5) O3 0.0298(6) 0.0298(6) 0.0431(6) -0.0009(5) -0.0050(5) 0.0062(5) C4 0.0224(6) 0.0231(7) 0.0223(6) -0.0006(5) -0.0014(5) -0.0008(5) N5 0.0244(6) 0.0215(5) 0.0243(6) -0.0005(4) 0.0016(5) -0.0009(5) C6 0.0248(7) 0.0214(6) 0.0282(7) 0.0045(5) 0.0053(5) 0.0080(6) O7 0.0268(5) 0.0292(5) 0.0358(5) 0.0088(4) 0.0043(4) -0.0009(4) C8 0.0359(8) 0.0304(7) 0.0249(7) 0.0032(6) 0.0065(6) 0.0021(7) C9 0.0330(8) 0.0272(7) 0.0217(6) 0.0020(5) -0.0009(6) 0.0002(6) C10 0.0219(6) 0.0241(7) 0.0248(7) -0.0006(5) -0.0012(5) -0.0021(5) C11 0.0193(6) 0.0184(6) 0.0241(6) -0.0035(5) 0.0022(5) 0.0022(5) C12 0.0195(6) 0.0191(6) 0.0227(6) -0.0019(5) 0.0000(5) 0.0034(5) C13 0.0204(6) 0.0224(6) 0.0231(6) -0.0006(5) -0.0008(5) 0.0021(5) C14 0.0182(6) 0.0218(6) 0.0259(6) -0.0037(5) 0.0011(5) 0.0013(5) C15 0.0221(6) 0.0207(6) 0.0241(6) -0.0027(5) 0.0027(5) 0.0049(5) C16 0.0239(7) 0.0217(6) 0.0224(6) -0.0049(5) 0.0016(5) 0.0072(6) C17 0.0206(6) 0.0219(7) 0.0248(7) -0.0064(5) -0.0005(5) 0.0009(5) C18 0.0285(7) 0.0306(7) 0.0225(7) -0.0073(6) -0.0016(5) 0.0064(6) C19 0.0388(8) 0.0344(8) 0.0191(6) -0.0034(6) 0.0009(6) 0.0109(7) C20 0.0364(8) 0.0304(8) 0.0237(7) -0.0001(5) 0.0088(6) 0.0057(7) C21 0.0259(7) 0.0254(7) 0.0273(7) -0.0022(5) 0.0054(6) 0.0025(6) C22 0.0528(10) 0.0206(7) 0.0346(8) -0.0006(6) -0.0069(7) 0.0002(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 9.9(4) 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 . 1.3388(19) yes O1 . C22 . 1.4410(19) yes C2 . O3 . 1.1958(19) yes C2 . C4 . 1.5384(19) yes C4 . N5 . 1.4590(18) yes C4 . C9 . 1.5484(18) yes C4 . C13 . 1.5293(19) yes N5 . C6 . 1.3507(19) yes N5 . C10 . 1.4597(18) yes C6 . O7 . 1.2278(18) yes C6 . C8 . 1.507(2) yes C8 . C9 . 1.529(2) yes C8 . H81 . 0.949 no C8 . H82 . 0.953 no C9 . H91 . 0.972 no C9 . H92 . 0.954 no C10 . C11 . 1.5097(18) yes C10 . H101 . 0.991 no C10 . H102 . 0.967 no C11 . C12 . 1.4264(19) yes C11 . C17 . 1.3723(19) yes C12 . C13 . 1.5112(18) yes C12 . C14 . 1.372(2) yes C13 . H131 . 0.976 no C13 . H132 . 0.958 no C14 . C15 . 1.4206(19) yes C14 . H141 . 0.944 no C15 . C16 . 1.424(2) yes C15 . C21 . 1.422(2) yes C16 . C17 . 1.415(2) yes C16 . C18 . 1.427(2) yes C17 . H171 . 0.931 no C18 . C19 . 1.371(2) yes C18 . H181 . 0.947 no C19 . C20 . 1.413(2) yes C19 . H191 . 0.916 no C20 . C21 . 1.369(2) yes C20 . H201 . 0.964 no C21 . H211 . 0.915 no C22 . H221 . 0.965 no C22 . H222 . 0.968 no C22 . H223 . 0.955 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 . C22 . 116.51(13) yes O1 . C2 . O3 . 124.86(14) yes O1 . C2 . C4 . 109.43(12) yes O3 . C2 . C4 . 125.71(13) yes C2 . C4 . N5 . 110.28(12) yes C2 . C4 . C9 . 110.59(11) yes N5 . C4 . C9 . 102.61(11) yes C2 . C4 . C13 . 109.39(11) yes N5 . C4 . C13 . 108.85(11) yes C9 . C4 . C13 . 114.90(12) yes C4 . N5 . C6 . 114.21(12) yes C4 . N5 . C10 . 123.03(11) yes C6 . N5 . C10 . 122.73(12) yes N5 . C6 . O7 . 124.29(14) yes N5 . C6 . C8 . 108.39(12) yes O7 . C6 . C8 . 127.31(13) yes C6 . C8 . C9 . 104.36(11) yes C6 . C8 . H81 . 111.2 no C9 . C8 . H81 . 115.0 no C6 . C8 . H82 . 108.8 no C9 . C8 . H82 . 110.9 no H81 . C8 . H82 . 106.5 no C4 . C9 . C8 . 104.09(12) yes C4 . C9 . H91 . 107.4 no C8 . C9 . H91 . 110.8 no C4 . C9 . H92 . 111.7 no C8 . C9 . H92 . 112.0 no H91 . C9 . H92 . 110.6 no N5 . C10 . C11 . 112.98(11) yes N5 . C10 . H101 . 107.7 no C11 . C10 . H101 . 109.1 no N5 . C10 . H102 . 108.9 no C11 . C10 . H102 . 108.2 no H101 . C10 . H102 . 109.9 no C10 . C11 . C12 . 120.31(12) yes C10 . C11 . C17 . 119.59(12) yes C12 . C11 . C17 . 120.10(12) yes C11 . C12 . C13 . 118.22(12) yes C11 . C12 . C14 . 119.70(12) yes C13 . C12 . C14 . 122.06(13) yes C4 . C13 . C12 . 109.18(11) yes C4 . C13 . H131 . 107.2 no C12 . C13 . H131 . 110.6 no C4 . C13 . H132 . 111.0 no C12 . C13 . H132 . 111.5 no H131 . C13 . H132 . 107.3 no C12 . C14 . C15 . 121.07(12) yes C12 . C14 . H141 . 119.2 no C15 . C14 . H141 . 119.7 no C14 . C15 . C16 . 119.14(12) yes C14 . C15 . C21 . 121.81(13) yes C16 . C15 . C21 . 119.01(13) yes C15 . C16 . C17 . 118.68(13) yes C15 . C16 . C18 . 119.04(13) yes C17 . C16 . C18 . 122.24(13) yes C16 . C17 . C11 . 121.29(13) yes C16 . C17 . H171 . 118.5 no C11 . C17 . H171 . 120.2 no C16 . C18 . C19 . 120.32(14) yes C16 . C18 . H181 . 118.3 no C19 . C18 . H181 . 121.3 no C18 . C19 . C20 . 120.48(14) yes C18 . C19 . H191 . 120.1 no C20 . C19 . H191 . 119.4 no C19 . C20 . C21 . 120.66(14) yes C19 . C20 . H201 . 119.4 no C21 . C20 . H201 . 119.9 no C15 . C21 . C20 . 120.47(14) yes C15 . C21 . H211 . 118.5 no C20 . C21 . H211 . 121.1 no O1 . C22 . H221 . 107.7 no O1 . C22 . H222 . 108.5 no H221 . C22 . H222 . 106.9 no O1 . C22 . H223 . 111.1 no H221 . C22 . H223 . 111.5 no H222 . C22 . H223 . 110.9 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 C8 . H82 . O7 4_745 137 0.95 2.50 3.269(2) yes C13 . H131 . O7 1_455 137 0.98 2.53 3.321(2) yes _iucr_refine_instruction_details_constraints ; # # Punched on 07/12/11 at 16:26:26 # #LIST 12 BLOCK SCALE X'S, U'S CONT ENANTIO RIDE C ( 8,X'S) H ( 81,X'S) H ( 82,X'S) RIDE C ( 9,X'S) H ( 91,X'S) H ( 92,X'S) RIDE C ( 10,X'S) H ( 101,X'S) H ( 102,X'S) RIDE C ( 13,X'S) H ( 131,X'S) H ( 132,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 20,X'S) H ( 201,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 221,X'S) H ( 222,X'S) H ( 223,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 07/12/11 at 16:26:26 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ;