data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof S Davies' _publ_contact_author_email STEVE.DAVIES@CHEM.OX.AC.UK _publ_section_title ; Ammonium directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-amino-cyclohexane-1,2-diol ; loop_ _publ_author_name 'Steve Davies' 'Caroline Aciro' 'Paul M Roberts' 'Angela J. Russell' 'Andrew D. Smith' 'James Thomson' # Attachment 'CCDC681276.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 681276' _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_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 10.83920(10) _cell_length_b 28.0222(3) _cell_length_c 12.21180(10) _cell_angle_alpha 90 _cell_angle_beta 110.5571(5) _cell_angle_gamma 90 _cell_volume 3473.00(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z x+1/2,-y+1/2,z 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 8 # Given Formula = C20 H25 N1 O2 # Dc = 1.19 Fooo = 1344.00 Mu = 0.76 M = 622.85 # Found Formula = C20 H25 N1 O2 # Dc = 1.19 FOOO = 1344.00 Mu = 0.76 M = 622.85 _chemical_formula_sum 'C20 H25 N1 O2' _chemical_formula_moiety 'C20 H25 N1 O2' _chemical_compound_source ? _chemical_formula_weight 311.42 _cell_measurement_reflns_used 8039 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.076 # Sheldrick geometric approximatio 0.98 0.99 # 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 0.99 # 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 'Nonius KappaCCD' _diffrn_measurement_device_type 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, 1997-2001).' _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 15636 _reflns_number_total 7908 _diffrn_reflns_av_R_equivalents 0.044 # Number of reflections with Friedels Law is 7908 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 7982 _diffrn_reflns_theta_min 5.145 _diffrn_reflns_theta_max 27.540 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.990 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -14 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 36 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 2.78 _oxford_diffrn_Wilson_scale 13.10 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _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>3.0\s(I) _refine_ls_number_reflns 4662 _refine_ls_number_restraints 0 _refine_ls_number_parameters 415 _oxford_refine_ls_R_factor_ref 0.0403 _refine_ls_wR_factor_ref 0.0426 _refine_ls_goodness_of_fit_ref 1.1211 _refine_ls_shift/su_max 0.000525 # The values computed from all data _oxford_reflns_number_all 7908 _refine_ls_R_factor_all 0.0850 _refine_ls_wR_factor_all 0.0861 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5130 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_gt 0.0459 # 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 . _refine_ls_structure_factor_coef F _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: 0.262 0.921E-01 0.701E-01 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. 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. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O 0.72217(12) 0.68750(4) 0.30551(9) 0.0366 1.0000 Uani . . . . . . . C2 C 0.64708(17) 0.72025(6) 0.21636(14) 0.0304 1.0000 Uani . . . . . . . C3 C 0.63476(16) 0.70108(6) 0.09597(13) 0.0289 1.0000 Uani . . . . . . . N4 N 0.58889(13) 0.65089(5) 0.08452(11) 0.0297 1.0000 Uani . . . . . . . C5 C 0.44643(16) 0.64576(6) 0.06172(15) 0.0336 1.0000 Uani . . . . . . . C6 C 0.41300(16) 0.59538(6) 0.08571(15) 0.0326 1.0000 Uani . . . . . . . C7 C 0.47490(19) 0.57455(7) 0.19392(16) 0.0401 1.0000 Uani . . . . . . . C8 C 0.4455(2) 0.52836(7) 0.21721(17) 0.0455 1.0000 Uani . . . . . . . C9 C 0.3528(2) 0.50232(7) 0.13189(17) 0.0444 1.0000 Uani . . . . . . . C10 C 0.2890(2) 0.52236(7) 0.02377(17) 0.0470 1.0000 Uani . . . . . . . C11 C 0.31908(18) 0.56869(7) 0.00100(16) 0.0425 1.0000 Uani . . . . . . . C12 C 0.62846(16) 0.62414(6) -0.00103(14) 0.0334 1.0000 Uani . . . . . . . C13 C 0.77132(16) 0.60893(6) 0.04495(14) 0.0310 1.0000 Uani . . . . . . . C14 C 0.84721(17) 0.60990(6) -0.02593(15) 0.0352 1.0000 Uani . . . . . . . C15 C 0.97425(18) 0.59188(6) 0.01361(16) 0.0398 1.0000 Uani . . . . . . . C16 C 1.02844(18) 0.57313(7) 0.12446(17) 0.0427 1.0000 Uani . . . . . . . C17 C 0.95445(19) 0.57249(7) 0.19680(16) 0.0441 1.0000 Uani . . . . . . . C18 C 0.82735(18) 0.59004(6) 0.15700(15) 0.0384 1.0000 Uani . . . . . . . C19 C 0.55134(17) 0.73576(6) 0.00202(14) 0.0341 1.0000 Uani . . . . . . . C20 C 0.61493(18) 0.78547(6) 0.02289(15) 0.0361 1.0000 Uani . . . . . . . C21 C 0.63344(18) 0.80374(6) 0.14563(15) 0.0370 1.0000 Uani . . . . . . . C22 C 0.71292(16) 0.76884(6) 0.23965(14) 0.0324 1.0000 Uani . . . . . . . O23 O 0.84293(11) 0.76739(4) 0.23583(10) 0.0366 1.0000 Uani . . . . . . . O24 O 0.52210(11) 0.78159(4) 0.42376(10) 0.0360 1.0000 Uani . . . . . . . C25 C 0.55358(16) 0.76523(6) 0.54159(13) 0.0297 1.0000 Uani . . . . . . . C26 C 0.64586(16) 0.80029(5) 0.62791(13) 0.0288 1.0000 Uani . . . . . . . N27 N 0.59155(13) 0.84922(5) 0.60570(11) 0.0300 1.0000 Uani . . . . . . . C28 C 0.48086(17) 0.85782(6) 0.64713(15) 0.0330 1.0000 Uani . . . . . . . C29 C 0.40964(16) 0.90384(6) 0.59963(14) 0.0312 1.0000 Uani . . . . . . . C30 C 0.37918(17) 0.93604(6) 0.67304(16) 0.0369 1.0000 Uani . . . . . . . C31 C 0.31191(18) 0.97794(6) 0.62985(17) 0.0414 1.0000 Uani . . . . . . . C32 C 0.27448(19) 0.98866(7) 0.51293(17) 0.0432 1.0000 Uani . . . . . . . C33 C 0.3054(2) 0.95733(7) 0.43934(17) 0.0495 1.0000 Uani . . . . . . . C34 C 0.3715(2) 0.91522(7) 0.48178(16) 0.0433 1.0000 Uani . . . . . . . C35 C 0.69379(17) 0.88542(6) 0.65560(15) 0.0345 1.0000 Uani . . . . . . . C36 C 0.79501(16) 0.88951(6) 0.59689(14) 0.0312 1.0000 Uani . . . . . . . C37 C 0.76585(18) 0.87979(6) 0.47912(15) 0.0383 1.0000 Uani . . . . . . . C38 C 0.8592(2) 0.88799(7) 0.42714(17) 0.0439 1.0000 Uani . . . . . . . C39 C 0.98152(19) 0.90624(6) 0.49230(18) 0.0426 1.0000 Uani . . . . . . . C40 C 1.01087(18) 0.91575(6) 0.60915(17) 0.0404 1.0000 Uani . . . . . . . C41 C 0.91835(17) 0.90720(6) 0.66135(16) 0.0351 1.0000 Uani . . . . . . . C42 C 0.67763(18) 0.78129(6) 0.75246(14) 0.0355 1.0000 Uani . . . . . . . C43 C 0.73971(18) 0.73169(6) 0.76520(15) 0.0380 1.0000 Uani . . . . . . . C44 C 0.64997(18) 0.69730(6) 0.67588(15) 0.0387 1.0000 Uani . . . . . . . C45 C 0.61656(16) 0.71608(6) 0.55202(15) 0.0334 1.0000 Uani . . . . . . . O46 O 0.73573(11) 0.71856(4) 0.52705(10) 0.0374 1.0000 Uani . . . . . . . H21 H 0.5550 0.7233 0.2197 0.0384 1.0000 Uiso R . . . . . . H31 H 0.7276 0.7008 0.0935 0.0366 1.0000 Uiso R . . . . . . H51 H 0.4267 0.6674 0.1189 0.0421 1.0000 Uiso R . . . . . . H52 H 0.3930 0.6549 -0.0229 0.0419 1.0000 Uiso R . . . . . . H71 H 0.5390 0.5935 0.2537 0.0506 1.0000 Uiso R . . . . . . H81 H 0.4910 0.5143 0.2949 0.0589 1.0000 Uiso R . . . . . . H91 H 0.3328 0.4696 0.1466 0.0570 1.0000 Uiso R . . . . . . H101 H 0.2249 0.5041 -0.0371 0.0579 1.0000 Uiso R . . . . . . H111 H 0.2732 0.5831 -0.0753 0.0514 1.0000 Uiso R . . . . . . H122 H 0.6097 0.6437 -0.0746 0.0442 1.0000 Uiso R . . . . . . H121 H 0.5734 0.5940 -0.0207 0.0445 1.0000 Uiso R . . . . . . H141 H 0.8111 0.6234 -0.1041 0.0445 1.0000 Uiso R . . . . . . H151 H 1.0250 0.5930 -0.0375 0.0505 1.0000 Uiso R . . . . . . H161 H 1.1182 0.5602 0.1515 0.0541 1.0000 Uiso R . . . . . . H171 H 0.9934 0.5593 0.2760 0.0549 1.0000 Uiso R . . . . . . H181 H 0.7743 0.5896 0.2075 0.0492 1.0000 Uiso R . . . . . . H192 H 0.4615 0.7373 0.0072 0.0424 1.0000 Uiso R . . . . . . H191 H 0.5410 0.7233 -0.0786 0.0418 1.0000 Uiso R . . . . . . H202 H 0.5585 0.8086 -0.0363 0.0447 1.0000 Uiso R . . . . . . H201 H 0.7052 0.7836 0.0153 0.0436 1.0000 Uiso R . . . . . . H211 H 0.6782 0.8358 0.1570 0.0464 1.0000 Uiso R . . . . . . H212 H 0.5437 0.8074 0.1516 0.0466 1.0000 Uiso R . . . . . . H221 H 0.7167 0.7800 0.3204 0.0417 1.0000 Uiso R . . . . . . H251 H 0.4685 0.7625 0.5585 0.0352 1.0000 Uiso R . . . . . . H261 H 0.7309 0.8005 0.6092 0.0347 1.0000 Uiso R . . . . . . H282 H 0.5140 0.8594 0.7352 0.0438 1.0000 Uiso R . . . . . . H281 H 0.4190 0.8305 0.6211 0.0440 1.0000 Uiso R . . . . . . H301 H 0.4080 0.9284 0.7572 0.0485 1.0000 Uiso R . . . . . . H311 H 0.2919 0.9994 0.6831 0.0542 1.0000 Uiso R . . . . . . H321 H 0.2265 1.0180 0.4822 0.0545 1.0000 Uiso R . . . . . . H331 H 0.2792 0.9648 0.3569 0.0627 1.0000 Uiso R . . . . . . H341 H 0.3910 0.8932 0.4286 0.0535 1.0000 Uiso R . . . . . . H351 H 0.6463 0.9165 0.6458 0.0461 1.0000 Uiso R . . . . . . H352 H 0.7405 0.8796 0.7417 0.0454 1.0000 Uiso R . . . . . . H371 H 0.6799 0.8672 0.4337 0.0498 1.0000 Uiso R . . . . . . H381 H 0.8375 0.8812 0.3441 0.0576 1.0000 Uiso R . . . . . . H391 H 1.0452 0.9123 0.4548 0.0560 1.0000 Uiso R . . . . . . H401 H 1.0968 0.9288 0.6551 0.0520 1.0000 Uiso R . . . . . . H411 H 0.9409 0.9138 0.7450 0.0457 1.0000 Uiso R . . . . . . H421 H 0.7380 0.8043 0.8085 0.0443 1.0000 Uiso R . . . . . . H422 H 0.5937 0.7793 0.7702 0.0453 1.0000 Uiso R . . . . . . H431 H 0.8257 0.7338 0.7516 0.0458 1.0000 Uiso R . . . . . . H432 H 0.7552 0.7193 0.8452 0.0461 1.0000 Uiso R . . . . . . H442 H 0.5656 0.6937 0.6911 0.0467 1.0000 Uiso R . . . . . . H441 H 0.6949 0.6654 0.6831 0.0461 1.0000 Uiso R . . . . . . H451 H 0.5531 0.6934 0.4954 0.0409 1.0000 Uiso R . . . . . . H231 H 0.8918 0.7493 0.2956 0.0592 1.0000 Uiso R . . . . . . H461 H 0.7197 0.7090 0.4545 0.0591 1.0000 Uiso R . . . . . . H241 H 0.4957 0.8113 0.4223 0.0553 1.0000 Uiso R . . . . . . H11 H 0.7048 0.6595 0.2717 0.0581 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 0.0455(7) 0.0348(6) 0.0281(6) 0.0029(5) 0.0112(5) 0.0001(5) C2 0.0325(8) 0.0323(9) 0.0282(8) 0.0021(7) 0.0129(7) 0.0017(7) C3 0.0288(8) 0.0314(8) 0.0273(8) 0.0013(6) 0.0108(6) 0.0002(6) N4 0.0303(7) 0.0311(7) 0.0299(7) -0.0017(6) 0.0135(6) 0.0007(6) C5 0.0291(8) 0.0363(9) 0.0351(9) 0.0022(7) 0.0109(7) 0.0015(7) C6 0.0321(9) 0.0342(9) 0.0348(9) -0.0008(7) 0.0158(7) 0.0004(7) C7 0.0450(10) 0.0389(10) 0.0351(9) -0.0023(8) 0.0123(8) -0.0068(8) C8 0.0542(12) 0.0404(10) 0.0403(10) 0.0034(8) 0.0146(9) -0.0055(9) C9 0.0527(12) 0.0342(10) 0.0519(11) -0.0025(8) 0.0254(10) -0.0055(9) C10 0.0487(11) 0.0455(11) 0.0454(11) -0.0097(9) 0.0148(9) -0.0127(9) C11 0.0416(10) 0.0463(11) 0.0372(10) -0.0001(8) 0.0110(8) -0.0047(9) C12 0.0367(9) 0.0359(9) 0.0279(8) -0.0023(7) 0.0118(7) 0.0015(7) C13 0.0347(9) 0.0265(8) 0.0326(8) -0.0031(7) 0.0128(7) 0.0004(7) C14 0.0402(10) 0.0350(9) 0.0316(8) -0.0012(7) 0.0139(7) -0.0006(7) C15 0.0389(10) 0.0415(10) 0.0431(10) -0.0057(8) 0.0196(8) -0.0004(8) C16 0.0359(10) 0.0432(11) 0.0472(11) -0.0053(8) 0.0122(8) 0.0051(8) C17 0.0489(11) 0.0451(11) 0.0358(10) 0.0032(8) 0.0116(8) 0.0132(9) C18 0.0436(10) 0.0406(10) 0.0334(9) 0.0008(8) 0.0166(8) 0.0077(8) C19 0.0361(9) 0.0369(9) 0.0282(8) 0.0025(7) 0.0099(7) 0.0015(7) C20 0.0381(9) 0.0330(9) 0.0336(9) 0.0064(7) 0.0082(7) 0.0031(7) C21 0.0390(10) 0.0309(9) 0.0391(9) 0.0014(7) 0.0112(8) 0.0023(7) C22 0.0340(9) 0.0357(9) 0.0298(8) -0.0001(7) 0.0140(7) 0.0017(7) O23 0.0305(6) 0.0431(7) 0.0354(6) 0.0063(5) 0.0103(5) -0.0008(5) O24 0.0374(6) 0.0359(7) 0.0300(6) -0.0016(5) 0.0060(5) 0.0032(5) C25 0.0270(8) 0.0329(9) 0.0274(8) 0.0005(7) 0.0074(7) 0.0000(7) C26 0.0287(8) 0.0285(8) 0.0287(8) 0.0003(6) 0.0094(7) -0.0003(6) N27 0.0310(7) 0.0284(7) 0.0325(7) -0.0021(6) 0.0136(6) -0.0030(6) C28 0.0340(9) 0.0338(9) 0.0349(9) 0.0003(7) 0.0167(7) -0.0017(7) C29 0.0292(8) 0.0302(9) 0.0352(9) -0.0023(7) 0.0127(7) -0.0048(7) C30 0.0390(10) 0.0388(10) 0.0364(9) -0.0043(7) 0.0177(8) -0.0040(8) C31 0.0426(10) 0.0359(10) 0.0521(11) -0.0079(8) 0.0247(9) -0.0009(8) C32 0.0444(11) 0.0330(10) 0.0513(11) 0.0006(8) 0.0156(9) 0.0035(8) C33 0.0629(13) 0.0458(11) 0.0370(10) 0.0006(8) 0.0140(9) 0.0085(10) C34 0.0543(12) 0.0394(10) 0.0358(9) -0.0045(8) 0.0154(8) 0.0064(9) C35 0.0361(9) 0.0335(9) 0.0363(9) -0.0062(7) 0.0158(7) -0.0061(7) C36 0.0329(9) 0.0245(8) 0.0374(9) 0.0006(7) 0.0141(7) -0.0008(7) C37 0.0387(10) 0.0391(10) 0.0381(9) -0.0059(8) 0.0146(8) -0.0097(8) C38 0.0524(11) 0.0449(11) 0.0404(10) -0.0054(8) 0.0238(9) -0.0083(9) C39 0.0418(11) 0.0371(10) 0.0578(12) 0.0009(8) 0.0288(9) -0.0027(8) C40 0.0321(9) 0.0380(10) 0.0504(11) -0.0008(8) 0.0139(8) -0.0032(8) C41 0.0338(9) 0.0327(9) 0.0369(9) 0.0022(7) 0.0098(7) 0.0000(7) C42 0.0416(10) 0.0351(9) 0.0292(8) 0.0000(7) 0.0114(7) 0.0003(8) C43 0.0412(10) 0.0390(10) 0.0312(9) 0.0051(7) 0.0092(7) 0.0015(8) C44 0.0408(10) 0.0325(9) 0.0424(10) 0.0057(8) 0.0141(8) 0.0024(8) C45 0.0312(9) 0.0293(9) 0.0369(9) -0.0035(7) 0.0084(7) -0.0027(7) O46 0.0322(6) 0.0451(7) 0.0344(6) -0.0057(5) 0.0112(5) 0.0047(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2869(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 . 1.4379(19) yes O1 . H11 . 0.876 no C2 . C3 . 1.526(2) yes C2 . C22 . 1.517(2) yes C2 . H21 . 1.017 no C3 . N4 . 1.482(2) yes C3 . C19 . 1.533(2) yes C3 . H31 . 1.017 no N4 . C5 . 1.477(2) yes N4 . C12 . 1.467(2) yes C5 . C6 . 1.511(2) yes C5 . H51 . 1.004 no C5 . H52 . 1.024 no C6 . C7 . 1.384(2) yes C6 . C11 . 1.388(2) yes C7 . C8 . 1.386(3) yes C7 . H71 . 0.970 no C8 . C9 . 1.376(3) yes C8 . H81 . 0.985 no C9 . C10 . 1.377(3) yes C9 . H91 . 0.972 no C10 . C11 . 1.390(3) yes C10 . H101 . 0.966 no C11 . H111 . 0.976 no C12 . C13 . 1.511(2) yes C12 . H122 . 1.010 no C12 . H121 . 1.013 no C13 . C14 . 1.388(2) yes C13 . C18 . 1.392(2) yes C14 . C15 . 1.385(2) yes C14 . H141 . 0.972 no C15 . C16 . 1.377(3) yes C15 . H151 . 0.967 no C16 . C17 . 1.386(3) yes C16 . H161 . 0.980 no C17 . C18 . 1.380(3) yes C17 . H171 . 0.981 no C18 . H181 . 0.980 no C19 . C20 . 1.535(2) yes C19 . H192 . 0.999 no C19 . H191 . 1.013 no C20 . C21 . 1.529(2) yes C20 . H202 . 1.003 no C20 . H201 . 1.016 no C21 . C22 . 1.524(2) yes C21 . H211 . 1.007 no C21 . H212 . 1.005 no C22 . O23 . 1.427(2) yes C22 . H221 . 1.021 no O23 . H231 . 0.893 no O24 . C25 . 1.4326(18) yes O24 . H241 . 0.877 no C25 . C26 . 1.529(2) yes C25 . C45 . 1.522(2) yes C25 . H251 . 1.016 no C26 . N27 . 1.479(2) yes C26 . C42 . 1.532(2) yes C26 . H261 . 1.025 no N27 . C28 . 1.476(2) yes N27 . C35 . 1.468(2) yes C28 . C29 . 1.510(2) yes C28 . H282 . 1.008 no C28 . H281 . 0.993 no C29 . C30 . 1.391(2) yes C29 . C34 . 1.388(2) yes C30 . C31 . 1.385(3) yes C30 . H301 . 0.987 no C31 . C32 . 1.374(3) yes C31 . H311 . 0.965 no C32 . C33 . 1.379(3) yes C32 . H321 . 0.975 no C33 . C34 . 1.383(3) yes C33 . H331 . 0.968 no C34 . H341 . 0.971 no C35 . C36 . 1.511(2) yes C35 . H351 . 0.998 no C35 . H352 . 1.008 no C36 . C37 . 1.387(2) yes C36 . C41 . 1.383(2) yes C37 . C38 . 1.389(2) yes C37 . H371 . 0.969 no C38 . C39 . 1.383(3) yes C38 . H381 . 0.975 no C39 . C40 . 1.375(3) yes C39 . H391 . 0.969 no C40 . C41 . 1.385(2) yes C40 . H401 . 0.974 no C41 . H411 . 0.980 no C42 . C43 . 1.528(2) yes C42 . H421 . 0.999 no C42 . H422 . 1.008 no C43 . C44 . 1.523(2) yes C43 . H431 . 1.004 no C43 . H432 . 0.993 no C44 . C45 . 1.520(2) yes C44 . H442 . 1.000 no C44 . H441 . 1.008 no C45 . O46 . 1.429(2) yes C45 . H451 . 1.010 no O46 . H461 . 0.882 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 . 104.2 no O1 . C2 . C3 . 109.84(13) yes O1 . C2 . C22 . 109.09(13) yes C3 . C2 . C22 . 111.89(13) yes O1 . C2 . H21 . 109.0 no C3 . C2 . H21 . 108.3 no C22 . C2 . H21 . 108.7 no C2 . C3 . N4 . 109.75(12) yes C2 . C3 . C19 . 109.08(13) yes N4 . C3 . C19 . 116.16(13) yes C2 . C3 . H31 . 106.2 no N4 . C3 . H31 . 107.0 no C19 . C3 . H31 . 108.3 no C3 . N4 . C5 . 113.84(12) yes C3 . N4 . C12 . 112.32(12) yes C5 . N4 . C12 . 111.33(13) yes N4 . C5 . C6 . 111.13(13) yes N4 . C5 . H51 . 105.9 no C6 . C5 . H51 . 107.8 no N4 . C5 . H52 . 110.4 no C6 . C5 . H52 . 109.9 no H51 . C5 . H52 . 111.6 no C5 . C6 . C7 . 120.69(15) yes C5 . C6 . C11 . 121.46(16) yes C7 . C6 . C11 . 117.85(16) yes C6 . C7 . C8 . 121.38(17) yes C6 . C7 . H71 . 117.8 no C8 . C7 . H71 . 120.8 no C7 . C8 . C9 . 119.96(18) yes C7 . C8 . H81 . 119.8 no C9 . C8 . H81 . 120.3 no C8 . C9 . C10 . 119.82(18) yes C8 . C9 . H91 . 120.7 no C10 . C9 . H91 . 119.4 no C9 . C10 . C11 . 119.90(18) yes C9 . C10 . H101 . 120.4 no C11 . C10 . H101 . 119.7 no C10 . C11 . C6 . 121.09(17) yes C10 . C11 . H111 . 120.0 no C6 . C11 . H111 . 118.9 no N4 . C12 . C13 . 113.40(13) yes N4 . C12 . H122 . 109.8 no C13 . C12 . H122 . 110.1 no N4 . C12 . H121 . 107.5 no C13 . C12 . H121 . 107.1 no H122 . C12 . H121 . 108.9 no C12 . C13 . C14 . 121.13(15) yes C12 . C13 . C18 . 120.59(15) yes C14 . C13 . C18 . 118.09(16) yes C13 . C14 . C15 . 120.65(16) yes C13 . C14 . H141 . 119.9 no C15 . C14 . H141 . 119.5 no C14 . C15 . C16 . 120.72(16) yes C14 . C15 . H151 . 118.9 no C16 . C15 . H151 . 120.3 no C15 . C16 . C17 . 119.27(17) yes C15 . C16 . H161 . 120.2 no C17 . C16 . H161 . 120.5 no C16 . C17 . C18 . 120.01(17) yes C16 . C17 . H171 . 119.2 no C18 . C17 . H171 . 120.8 no C13 . C18 . C17 . 121.23(16) yes C13 . C18 . H181 . 118.3 no C17 . C18 . H181 . 120.5 no C3 . C19 . C20 . 109.79(14) yes C3 . C19 . H192 . 108.2 no C20 . C19 . H192 . 110.0 no C3 . C19 . H191 . 110.1 no C20 . C19 . H191 . 111.3 no H192 . C19 . H191 . 107.3 no C19 . C20 . C21 . 111.31(14) yes C19 . C20 . H202 . 110.0 no C21 . C20 . H202 . 109.1 no C19 . C20 . H201 . 109.2 no C21 . C20 . H201 . 107.9 no H202 . C20 . H201 . 109.3 no C20 . C21 . C22 . 111.62(14) yes C20 . C21 . H211 . 108.9 no C22 . C21 . H211 . 110.5 no C20 . C21 . H212 . 107.9 no C22 . C21 . H212 . 108.4 no H211 . C21 . H212 . 109.4 no C21 . C22 . C2 . 109.30(14) yes C21 . C22 . O23 . 107.29(13) yes C2 . C22 . O23 . 111.91(13) yes C21 . C22 . H221 . 110.6 no C2 . C22 . H221 . 108.2 no O23 . C22 . H221 . 109.5 no C22 . O23 . H231 . 107.3 no C25 . O24 . H241 . 106.5 no O24 . C25 . C26 . 110.75(13) yes O24 . C25 . C45 . 108.38(13) yes C26 . C25 . C45 . 110.98(13) yes O24 . C25 . H251 . 108.4 no C26 . C25 . H251 . 109.1 no C45 . C25 . H251 . 109.2 no C25 . C26 . N27 . 110.33(13) yes C25 . C26 . C42 . 109.01(13) yes N27 . C26 . C42 . 116.12(13) yes C25 . C26 . H261 . 105.8 no N27 . C26 . H261 . 106.6 no C42 . C26 . H261 . 108.5 no C26 . N27 . C28 . 114.04(12) yes C26 . N27 . C35 . 111.75(13) yes C28 . N27 . C35 . 109.33(12) yes N27 . C28 . C29 . 112.03(13) yes N27 . C28 . H282 . 110.1 no C29 . C28 . H282 . 108.4 no N27 . C28 . H281 . 107.7 no C29 . C28 . H281 . 109.8 no H282 . C28 . H281 . 108.8 no C28 . C29 . C30 . 120.75(15) yes C28 . C29 . C34 . 121.34(15) yes C30 . C29 . C34 . 117.90(16) yes C29 . C30 . C31 . 121.12(17) yes C29 . C30 . H301 . 118.0 no C31 . C30 . H301 . 120.9 no C30 . C31 . C32 . 120.34(17) yes C30 . C31 . H311 . 118.9 no C32 . C31 . H311 . 120.7 no C31 . C32 . C33 . 119.17(18) yes C31 . C32 . H321 . 120.5 no C33 . C32 . H321 . 120.3 no C32 . C33 . C34 . 120.75(18) yes C32 . C33 . H331 . 119.4 no C34 . C33 . H331 . 119.9 no C29 . C34 . C33 . 120.71(17) yes C29 . C34 . H341 . 119.5 no C33 . C34 . H341 . 119.8 no N27 . C35 . C36 . 115.07(13) yes N27 . C35 . H351 . 105.8 no C36 . C35 . H351 . 107.8 no N27 . C35 . H352 . 110.6 no C36 . C35 . H352 . 109.0 no H351 . C35 . H352 . 108.4 no C35 . C36 . C37 . 122.55(15) yes C35 . C36 . C41 . 118.35(15) yes C37 . C36 . C41 . 118.90(15) yes C36 . C37 . C38 . 120.27(17) yes C36 . C37 . H371 . 119.2 no C38 . C37 . H371 . 120.5 no C37 . C38 . C39 . 120.21(17) yes C37 . C38 . H381 . 119.6 no C39 . C38 . H381 . 120.1 no C38 . C39 . C40 . 119.65(17) yes C38 . C39 . H391 . 119.5 no C40 . C39 . H391 . 120.9 no C39 . C40 . C41 . 120.21(17) yes C39 . C40 . H401 . 119.8 no C41 . C40 . H401 . 120.0 no C40 . C41 . C36 . 120.75(17) yes C40 . C41 . H411 . 119.4 no C36 . C41 . H411 . 119.8 no C26 . C42 . C43 . 110.76(14) yes C26 . C42 . H421 . 108.7 no C43 . C42 . H421 . 111.0 no C26 . C42 . H422 . 109.1 no C43 . C42 . H422 . 109.0 no H421 . C42 . H422 . 108.2 no C42 . C43 . C44 . 110.79(14) yes C42 . C43 . H431 . 109.4 no C44 . C43 . H431 . 108.4 no C42 . C43 . H432 . 109.5 no C44 . C43 . H432 . 109.2 no H431 . C43 . H432 . 109.6 no C43 . C44 . C45 . 111.26(14) yes C43 . C44 . H442 . 109.1 no C45 . C44 . H442 . 107.8 no C43 . C44 . H441 . 109.4 no C45 . C44 . H441 . 109.5 no H442 . C44 . H441 . 109.8 no C25 . C45 . C44 . 109.85(14) yes C25 . C45 . O46 . 110.52(13) yes C44 . C45 . O46 . 108.16(14) yes C25 . C45 . H451 . 109.5 no C44 . C45 . H451 . 109.3 no O46 . C45 . H451 . 109.5 no C45 . O46 . H461 . 109.0 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 C2 . H21 . O23 4_465 177 1.02 2.39 3.405(3) yes C25 . H251 . O46 4_465 154 1.02 2.47 3.417(3) yes C28 . H281 . O46 4_465 165 0.99 2.36 3.325(3) yes O23 . H231 . O24 4_565 169 0.89 1.91 2.791(3) yes O46 . H461 . O1 . 169 0.88 1.93 2.796(3) yes O1 . H11 . N4 . 122 0.88 2.20 2.772(3) yes