# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_1 _database_code_depnum_ccdc_archive 'CCDC 780761' #TrackingRef 'kubl4.cif' _exptl_special_details ; ; _refine_special_details ; 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. ; # End of 'script/refcif.dat' #end of refcif _cell_length_a 8.0838(9) _cell_length_b 11.4841(10) _cell_length_c 16.815(2) _cell_angle_alpha 88.448(9) _cell_angle_beta 82.135(9) _cell_angle_gamma 81.667(9) _cell_volume 1529.9(3) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 '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' 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' 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' _cell_formula_units_Z 2 # Given Formula = C38 H6 Cl4 N1 O1.50 # Dc = 1.39 Fooo = 696.00 Mu = 4.21 M = 642.28 # Found Formula = C31 H39 Cl4 N1 O6 # Dc = 1.44 FOOO = 696.00 Mu = 4.32 M = 663.46 _chemical_formula_sum 'C31 H39 Cl4 N1 O6' _chemical_formula_moiety 'C30 H38 N O6, C H Cl3, Cl ' _chemical_compound_source ? _chemical_formula_weight 663.46 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 180 _exptl_crystal_description 'triangular platelet' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_max 0.500 _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.432 # Sheldrick geometric approximatio 0.84 0.96 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details ; Gaussian Integration (Busing and Levy, 1957) ; _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device 'Stoe IPDS' _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 'IPDS (Stoe & Cie, 1996)' _computing_cell_refinement 'IPDS (Stoe & Cie, 1996)' _computing_data_reduction 'XRED (Stoe & Cie 1996)' _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_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 180 _diffrn_reflns_number 20096 _reflns_number_total 10127 _diffrn_reflns_av_R_equivalents 0.058 # Number of reflections with Friedels Law is 10127 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 6003 _diffrn_reflns_theta_min 2.162 _diffrn_reflns_theta_max 32.131 _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 30.845 _diffrn_measured_fraction_theta_full 0.981 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -11 _reflns_limit_h_max 12 _reflns_limit_k_min -16 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _oxford_diffrn_Wilson_B_factor 2.51 _oxford_diffrn_Wilson_scale 0.80 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.63 _refine_diff_density_max 0.48 # 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>-10.0\s(I) _refine_ls_number_reflns 5798 _refine_ls_number_restraints 0 _refine_ls_number_parameters 379 _oxford_refine_ls_R_factor_ref 0.0575 _refine_ls_wR_factor_ref 0.0709 _refine_ls_goodness_of_fit_ref 1.2602 _refine_ls_shift/su_max 0.0006370 _refine_ls_shift/su_mean 7.3113880 # The values computed from all data _oxford_reflns_number_all 5798 _refine_ls_R_factor_all 0.0575 _refine_ls_wR_factor_all 0.0709 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5063 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_gt 0.0692 # 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 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, 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: 20.5 21.3 6.06 ; # 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cl1 Cl 0.78489(8) 0.89876(5) 0.56890(3) 0.0291 1.0000 Uani . . . . . . . Cl2 Cl 0.81123(10) 0.81850(7) 0.75317(4) 0.0526 1.0000 Uani . . . . . . . C3 C 0.8463(4) 0.7452(2) 0.84039(15) 0.0423 1.0000 Uani . . . . . . . Cl4 Cl 0.70242(12) 0.64925(7) 0.86638(4) 0.0578 1.0000 Uani . . . . . . . Cl5 Cl 0.84309(14) 0.84094(7) 0.91755(5) 0.0710 1.0000 Uani . . . . . . . H31 H 0.9608 0.7029 0.8312 0.0513 1.0000 Uiso R . . . . . . O7 O 1.3439(2) 0.43297(13) 0.42013(9) 0.0294 1.0000 Uani . . . . . . . C8 C 1.2256(3) 0.51629(18) 0.39933(13) 0.0211 1.0000 Uani . . . . . . . C9 C 1.1715(3) 0.52750(18) 0.32605(12) 0.0215 1.0000 Uani . . . . . . . C10 C 1.0543(3) 0.61939(18) 0.30835(12) 0.0185 1.0000 Uani . . . . . . . C11 C 0.9918(3) 0.70218(18) 0.36473(12) 0.0178 1.0000 Uani . . . . . . . C12 C 0.8750(3) 0.80811(17) 0.34784(11) 0.0173 1.0000 Uani . . . . . . . N13 N 0.7213(2) 0.82317(15) 0.40787(10) 0.0180 1.0000 Uani . . . . . . . C14 C 0.6389(3) 0.7161(2) 0.42323(13) 0.0251 1.0000 Uani . . . . . . . C15 C 0.5537(3) 0.6890(2) 0.35421(15) 0.0317 1.0000 Uani . . . . . . . C16 C 0.4298(3) 0.7893(2) 0.33464(15) 0.0333 1.0000 Uani . . . . . . . C17 C 0.5128(3) 0.8979(2) 0.31862(13) 0.0256 1.0000 Uani . . . . . . . C18 C 0.5977(3) 0.92445(18) 0.38891(12) 0.0211 1.0000 Uani . . . . . . . C19 C 0.6784(3) 1.03459(18) 0.38278(13) 0.0245 1.0000 Uani . . . . . . . C20 C 0.8415(3) 1.02565(19) 0.32976(12) 0.0233 1.0000 Uani . . . . . . . C21 C 0.9544(3) 0.91831(18) 0.34760(13) 0.0213 1.0000 Uani . . . . . . . H211 H 0.9876 0.9297 0.3996 0.0254 1.0000 Uiso R . . . . . . H212 H 1.0524 0.9080 0.3101 0.0267 1.0000 Uiso R . . . . . . O24 O 0.8150(2) 1.01907(13) 0.24684(8) 0.0264 1.0000 Uani . . . . . . . C25 C 0.7672(3) 1.1198(2) 0.21168(14) 0.0343 1.0000 Uani . . . . . . . O26 O 0.7565(3) 1.21306(15) 0.24137(11) 0.0502 1.0000 Uani . . . . . . . C27 C 0.7293(4) 1.1043(3) 0.13059(16) 0.0493 1.0000 Uani . . . . . . . C28 C 0.7277(5) 1.0062(3) 0.09833(17) 0.0591 1.0000 Uani . . . . . . . H281 H 0.6992 1.0056 0.0453 0.0712 1.0000 Uiso R . . . . . . H282 H 0.7556 0.9342 0.1267 0.0697 1.0000 Uiso R . . . . . . H271 H 0.7019 1.1725 0.1026 0.0593 1.0000 Uiso R . . . . . . H201 H 0.8947 1.0956 0.3354 0.0274 1.0000 Uiso R . . . . . . H192 H 0.7034 1.0499 0.4348 0.0280 1.0000 Uiso R . . . . . . H191 H 0.5996 1.0976 0.3664 0.0286 1.0000 Uiso R . . . . . . H181 H 0.5173 0.9321 0.4333 0.0234 1.0000 Uiso R . . . . . . H171 H 0.4310 0.9660 0.3106 0.0299 1.0000 Uiso R . . . . . . H172 H 0.5930 0.8865 0.2720 0.0297 1.0000 Uiso R . . . . . . H161 H 0.3448 0.8040 0.3801 0.0399 1.0000 Uiso R . . . . . . H162 H 0.3809 0.7713 0.2885 0.0405 1.0000 Uiso R . . . . . . H151 H 0.5000 0.6237 0.3708 0.0377 1.0000 Uiso R . . . . . . H152 H 0.6353 0.6669 0.3087 0.0373 1.0000 Uiso R . . . . . . H141 H 0.5574 0.7333 0.4695 0.0295 1.0000 Uiso R . . . . . . H142 H 0.7234 0.6509 0.4332 0.0301 1.0000 Uiso R . . . . . . H121 H 0.8405 0.7993 0.2976 0.0206 1.0000 Uiso R . . . . . . C45 C 1.0449(3) 0.68972(19) 0.43989(12) 0.0202 1.0000 Uani . . . . . . . C46 C 1.1563(3) 0.59785(19) 0.45773(12) 0.0202 1.0000 Uani . . . . . . . O47 O 1.2131(2) 0.57922(14) 0.52913(9) 0.0284 1.0000 Uani . . . . . . . C48 C 1.1430(3) 0.6614(2) 0.58873(13) 0.0330 1.0000 Uani . . . . . . . H481 H 1.1911 0.6355 0.6355 0.0492 1.0000 Uiso R . . . . . . H483 H 1.1703 0.7381 0.5725 0.0491 1.0000 Uiso R . . . . . . H482 H 1.0254 0.6658 0.5980 0.0494 1.0000 Uiso R . . . . . . H451 H 0.9987 0.7472 0.4781 0.0233 1.0000 Uiso R . . . . . . C53 C 1.0000(3) 0.62199(18) 0.22779(12) 0.0200 1.0000 Uani . . . . . . . C54 C 1.0541(3) 0.69805(19) 0.16959(12) 0.0230 1.0000 Uani . . . . . . . O55 O 1.1565(2) 0.77167(14) 0.19085(9) 0.0298 1.0000 Uani . . . . . . . C56 C 1.2034(4) 0.8589(2) 0.13745(15) 0.0384 1.0000 Uani . . . . . . . O57 O 1.3141(3) 0.81645(19) 0.07321(10) 0.0495 1.0000 Uani . . . . . . . C58 C 1.4667(4) 0.7597(4) 0.0946(2) 0.0733 1.0000 Uani . . . . . . . H581 H 1.5437 0.7373 0.0470 0.1098 1.0000 Uiso R . . . . . . H582 H 1.5098 0.8146 0.1253 0.1094 1.0000 Uiso R . . . . . . H583 H 1.4483 0.6889 0.1255 0.1099 1.0000 Uiso R . . . . . . H562 H 1.2544 0.9126 0.1667 0.0449 1.0000 Uiso R . . . . . . H561 H 1.1015 0.9017 0.1201 0.0461 1.0000 Uiso R . . . . . . C64 C 1.0064(3) 0.6956(2) 0.09446(13) 0.0300 1.0000 Uani . . . . . . . C65 C 0.9041(3) 0.6173(2) 0.07840(13) 0.0300 1.0000 Uani . . . . . . . C66 C 0.8485(3) 0.5400(2) 0.13442(13) 0.0253 1.0000 Uani . . . . . . . C67 C 0.8986(3) 0.54377(19) 0.20930(12) 0.0229 1.0000 Uani . . . . . . . H671 H 0.8624 0.4900 0.2474 0.0271 1.0000 Uiso R . . . . . . C69 C 0.7416(3) 0.4541(2) 0.11903(14) 0.0331 1.0000 Uani . . . . . . . C70 C 0.6907(4) 0.4373(2) 0.05114(16) 0.0421 1.0000 Uani . . . . . . . H702 H 0.7221 0.4815 0.0061 0.0504 1.0000 Uiso R . . . . . . H701 H 0.6211 0.3810 0.0457 0.0507 1.0000 Uiso R . . . . . . H691 H 0.7093 0.4065 0.1619 0.0394 1.0000 Uiso R . . . . . . H651 H 0.8709 0.6174 0.0275 0.0359 1.0000 Uiso R . . . . . . H641 H 1.0438 0.7467 0.0557 0.0367 1.0000 Uiso R . . . . . . H91 H 1.2178 0.4724 0.2868 0.0255 1.0000 Uiso R . . . . . . C77 C 1.4290(3) 0.3564(2) 0.36046(15) 0.0349 1.0000 Uani . . . . . . . H772 H 1.5155 0.3076 0.3839 0.0512 1.0000 Uiso R . . . . . . H771 H 1.4759 0.4008 0.3168 0.0510 1.0000 Uiso R . . . . . . H773 H 1.3526 0.3076 0.3439 0.0511 1.0000 Uiso R . . . . . . H131 H 0.7482 0.8391 0.4532 0.0285 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 Cl1 0.0306(3) 0.0352(3) 0.0212(3) -0.0076(2) -0.0048(2) -0.0008(3) Cl2 0.0651(5) 0.0651(5) 0.0339(4) 0.0127(3) -0.0132(3) -0.0270(4) C3 0.0519(18) 0.0411(16) 0.0342(14) 0.0034(12) -0.0050(13) -0.0095(14) Cl4 0.0827(6) 0.0536(5) 0.0402(4) 0.0005(3) 0.0028(4) -0.0310(4) Cl5 0.1283(9) 0.0553(5) 0.0396(4) 0.0011(3) -0.0248(5) -0.0350(5) O7 0.0339(10) 0.0234(8) 0.0289(8) -0.0004(7) -0.0108(7) 0.0087(7) C8 0.0216(12) 0.0158(10) 0.0260(11) 0.0033(8) -0.0061(9) -0.0007(9) C9 0.0255(12) 0.0183(11) 0.0200(10) -0.0026(8) -0.0017(9) -0.0013(9) C10 0.0204(11) 0.0183(11) 0.0175(10) 0.0001(8) -0.0038(8) -0.0040(9) C11 0.0176(11) 0.0181(11) 0.0183(10) -0.0007(8) -0.0034(8) -0.0031(9) C12 0.0183(11) 0.0184(10) 0.0147(10) -0.0009(8) -0.0026(8) -0.0007(9) N13 0.0185(9) 0.0202(9) 0.0153(8) -0.0007(7) -0.0028(7) -0.0022(8) C14 0.0228(12) 0.0236(12) 0.0294(12) 0.0047(9) -0.0025(9) -0.0072(10) C15 0.0270(13) 0.0309(13) 0.0411(14) -0.0043(11) -0.0062(11) -0.0149(11) C16 0.0224(13) 0.0436(15) 0.0364(14) -0.0027(11) -0.0096(11) -0.0076(11) C17 0.0215(12) 0.0312(13) 0.0239(11) -0.0011(9) -0.0070(9) 0.0008(10) C18 0.0183(11) 0.0218(11) 0.0215(11) -0.0012(9) -0.0021(9) 0.0027(9) C19 0.0294(13) 0.0189(11) 0.0232(11) -0.0024(9) -0.0030(9) 0.0034(10) C20 0.0317(13) 0.0190(11) 0.0199(11) -0.0005(8) -0.0036(9) -0.0057(10) C21 0.0208(12) 0.0210(11) 0.0225(11) -0.0017(9) -0.0022(9) -0.0042(9) O24 0.0372(10) 0.0219(8) 0.0193(7) 0.0023(6) -0.0034(7) -0.0028(7) C25 0.0444(16) 0.0290(14) 0.0284(13) 0.0071(11) -0.0062(11) -0.0015(12) O26 0.0852(16) 0.0228(10) 0.0428(11) 0.0053(8) -0.0195(11) 0.0012(10) C27 0.074(2) 0.0422(17) 0.0323(14) 0.0095(12) -0.0163(14) -0.0017(15) C28 0.090(3) 0.059(2) 0.0318(15) 0.0030(14) -0.0209(16) -0.0135(19) C45 0.0215(12) 0.0218(11) 0.0178(10) -0.0034(8) -0.0036(9) -0.0029(9) C46 0.0215(11) 0.0219(11) 0.0185(10) 0.0028(8) -0.0066(9) -0.0038(9) O47 0.0352(10) 0.0307(9) 0.0200(8) 0.0003(7) -0.0133(7) 0.0020(7) C48 0.0413(15) 0.0397(14) 0.0191(11) -0.0032(10) -0.0106(10) -0.0034(12) C53 0.0232(12) 0.0180(11) 0.0175(10) -0.0029(8) -0.0027(9) 0.0016(9) C54 0.0268(12) 0.0221(11) 0.0203(11) -0.0030(9) -0.0021(9) -0.0047(10) O55 0.0397(10) 0.0334(9) 0.0209(8) 0.0016(7) -0.0056(7) -0.0195(8) C56 0.0532(18) 0.0338(14) 0.0329(14) 0.0054(11) -0.0066(12) -0.0224(13) O57 0.0576(14) 0.0712(14) 0.0262(9) -0.0003(9) 0.0011(9) -0.0375(11) C58 0.045(2) 0.122(3) 0.056(2) -0.025(2) 0.0046(16) -0.026(2) C64 0.0407(15) 0.0324(13) 0.0186(11) 0.0047(10) -0.0048(10) -0.0112(12) C65 0.0406(15) 0.0342(13) 0.0183(11) 0.0010(9) -0.0104(10) -0.0100(11) C66 0.0292(13) 0.0244(12) 0.0237(11) -0.0028(9) -0.0070(10) -0.0047(10) C67 0.0278(13) 0.0202(11) 0.0201(11) 0.0006(9) -0.0029(9) -0.0011(10) C69 0.0412(15) 0.0321(14) 0.0293(13) 0.0008(10) -0.0082(11) -0.0135(12) C70 0.0521(18) 0.0448(16) 0.0370(14) -0.0001(12) -0.0149(13) -0.0241(14) C77 0.0345(15) 0.0276(13) 0.0389(14) -0.0036(11) -0.0076(11) 0.0110(11) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.224(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 Cl2 . C3 . 1.708(3) yes C3 . Cl4 . 1.722(3) yes C3 . Cl5 . 1.718(3) yes C3 . H31 . 0.975 no O7 . C8 . 1.327(3) yes O7 . C77 . 1.392(3) yes C8 . C9 . 1.360(3) yes C8 . C46 . 1.380(3) yes C9 . C10 . 1.368(3) yes C9 . H91 . 0.928 no C10 . C11 . 1.355(3) yes C10 . C53 . 1.478(3) yes C11 . C12 . 1.474(3) yes C11 . C45 . 1.386(3) yes C12 . N13 . 1.482(2) yes C12 . C21 . 1.499(3) yes C12 . H121 . 0.937 no N13 . C14 . 1.482(3) yes N13 . C18 . 1.478(3) yes N13 . H131 . 0.852 no C14 . C15 . 1.490(3) yes C14 . H141 . 0.954 no C14 . H142 . 0.965 no C15 . C16 . 1.474(3) yes C15 . H151 . 0.936 no C15 . H152 . 0.954 no C16 . C17 . 1.501(3) yes C16 . H161 . 0.956 no C16 . H162 . 0.957 no C17 . C18 . 1.504(3) yes C17 . H171 . 0.967 no C17 . H172 . 0.945 no C18 . C19 . 1.500(3) yes C18 . H181 . 0.917 no C19 . C20 . 1.479(3) yes C19 . H192 . 0.951 no C19 . H191 . 0.953 no C20 . C21 . 1.473(3) yes C20 . O24 . 1.445(2) yes C20 . H201 . 0.976 no C21 . H211 . 0.967 no C21 . H212 . 0.937 no O24 . C25 . 1.316(3) yes C25 . O26 . 1.181(3) yes C25 . C27 . 1.459(3) yes C27 . C28 . 1.266(4) yes C27 . H271 . 0.917 no C28 . H281 . 0.952 no C28 . H282 . 0.957 no C45 . C46 . 1.340(3) yes C45 . H451 . 0.935 no C46 . O47 . 1.344(2) yes O47 . C48 . 1.399(3) yes C48 . H481 . 0.947 no C48 . H483 . 0.963 no C48 . H482 . 0.936 no C53 . C54 . 1.363(3) yes C53 . C67 . 1.368(3) yes C54 . O55 . 1.352(3) yes C54 . C64 . 1.373(3) yes O55 . C56 . 1.386(3) yes C56 . O57 . 1.358(3) yes C56 . H562 . 0.969 no C56 . H561 . 0.972 no O57 . C58 . 1.397(4) yes C58 . H581 . 0.961 no C58 . H582 . 0.956 no C58 . H583 . 0.972 no C64 . C65 . 1.362(3) yes C64 . H641 . 0.915 no C65 . C66 . 1.354(3) yes C65 . H651 . 0.932 no C66 . C67 . 1.378(3) yes C66 . C69 . 1.452(3) yes C67 . H671 . 0.925 no C69 . C70 . 1.294(3) yes C69 . H691 . 0.926 no C70 . H702 . 0.927 no C70 . H701 . 0.930 no C77 . H772 . 0.953 no C77 . H771 . 0.949 no C77 . H773 . 0.964 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 Cl2 . C3 . Cl4 . 111.21(16) yes Cl2 . C3 . Cl5 . 111.55(16) yes Cl4 . C3 . Cl5 . 110.35(15) yes Cl2 . C3 . H31 . 106.6 no Cl4 . C3 . H31 . 110.7 no Cl5 . C3 . H31 . 106.2 no C8 . O7 . C77 . 117.43(17) yes O7 . C8 . C9 . 125.3(2) yes O7 . C8 . C46 . 115.79(19) yes C9 . C8 . C46 . 118.9(2) yes C8 . C9 . C10 . 121.6(2) yes C8 . C9 . H91 . 118.9 no C10 . C9 . H91 . 119.5 no C9 . C10 . C11 . 119.36(19) yes C9 . C10 . C53 . 117.51(19) yes C11 . C10 . C53 . 123.12(19) yes C10 . C11 . C12 . 122.25(18) yes C10 . C11 . C45 . 119.1(2) yes C12 . C11 . C45 . 118.64(19) yes C11 . C12 . N13 . 111.60(16) yes C11 . C12 . C21 . 112.35(17) yes N13 . C12 . C21 . 107.56(16) yes C11 . C12 . H121 . 108.5 no N13 . C12 . H121 . 107.3 no C21 . C12 . H121 . 109.4 no C12 . N13 . C14 . 114.53(16) yes C12 . N13 . C18 . 112.36(15) yes C14 . N13 . C18 . 110.57(16) yes C12 . N13 . H131 . 109.1 no C14 . N13 . H131 . 104.4 no C18 . N13 . H131 . 105.1 no N13 . C14 . C15 . 111.60(18) yes N13 . C14 . H141 . 105.5 no C15 . C14 . H141 . 109.8 no N13 . C14 . H142 . 108.7 no C15 . C14 . H142 . 109.9 no H141 . C14 . H142 . 111.3 no C14 . C15 . C16 . 111.4(2) yes C14 . C15 . H151 . 105.3 no C16 . C15 . H151 . 110.7 no C14 . C15 . H152 . 110.1 no C16 . C15 . H152 . 110.9 no H151 . C15 . H152 . 108.3 no C15 . C16 . C17 . 110.42(19) yes C15 . C16 . H161 . 108.2 no C17 . C16 . H161 . 108.0 no C15 . C16 . H162 . 109.8 no C17 . C16 . H162 . 109.8 no H161 . C16 . H162 . 110.5 no C16 . C17 . C18 . 110.66(19) yes C16 . C17 . H171 . 111.2 no C18 . C17 . H171 . 106.9 no C16 . C17 . H172 . 109.2 no C18 . C17 . H172 . 109.9 no H171 . C17 . H172 . 108.9 no C17 . C18 . N13 . 110.92(17) yes C17 . C18 . C19 . 116.35(18) yes N13 . C18 . C19 . 109.79(17) yes C17 . C18 . H181 . 107.6 no N13 . C18 . H181 . 104.6 no C19 . C18 . H181 . 106.9 no C18 . C19 . C20 . 114.66(18) yes C18 . C19 . H192 . 107.2 no C20 . C19 . H192 . 105.4 no C18 . C19 . H191 . 108.5 no C20 . C19 . H191 . 111.2 no H192 . C19 . H191 . 109.8 no C19 . C20 . C21 . 111.11(18) yes C19 . C20 . O24 . 110.18(18) yes C21 . C20 . O24 . 107.19(17) yes C19 . C20 . H201 . 109.9 no C21 . C20 . H201 . 110.6 no O24 . C20 . H201 . 107.7 no C12 . C21 . C20 . 113.67(18) yes C12 . C21 . H211 . 110.3 no C20 . C21 . H211 . 106.6 no C12 . C21 . H212 . 107.3 no C20 . C21 . H212 . 111.1 no H211 . C21 . H212 . 107.8 no C20 . O24 . C25 . 116.09(17) yes O24 . C25 . O26 . 124.6(2) yes O24 . C25 . C27 . 112.5(2) yes O26 . C25 . C27 . 122.9(2) yes C25 . C27 . C28 . 125.1(3) yes C25 . C27 . H271 . 115.5 no C28 . C27 . H271 . 119.3 no C27 . C28 . H281 . 118.7 no C27 . C28 . H282 . 120.5 no H281 . C28 . H282 . 120.8 no C11 . C45 . C46 . 121.4(2) yes C11 . C45 . H451 . 117.6 no C46 . C45 . H451 . 121.0 no C8 . C46 . C45 . 119.59(19) yes C8 . C46 . O47 . 115.40(19) yes C45 . C46 . O47 . 125.0(2) yes C46 . O47 . C48 . 115.71(17) yes O47 . C48 . H481 . 106.2 no O47 . C48 . H483 . 109.9 no H481 . C48 . H483 . 110.6 no O47 . C48 . H482 . 111.1 no H481 . C48 . H482 . 110.7 no H483 . C48 . H482 . 108.4 no C10 . C53 . C54 . 121.42(19) yes C10 . C53 . C67 . 119.98(19) yes C54 . C53 . C67 . 118.55(19) yes C53 . C54 . O55 . 115.91(18) yes C53 . C54 . C64 . 120.1(2) yes O55 . C54 . C64 . 123.9(2) yes C54 . O55 . C56 . 119.13(17) yes O55 . C56 . O57 . 113.2(2) yes O55 . C56 . H562 . 107.3 no O57 . C56 . H562 . 109.4 no O55 . C56 . H561 . 108.0 no O57 . C56 . H561 . 110.6 no H562 . C56 . H561 . 108.2 no C56 . O57 . C58 . 112.9(2) yes O57 . C58 . H581 . 109.5 no O57 . C58 . H582 . 106.8 no H581 . C58 . H582 . 110.7 no O57 . C58 . H583 . 110.0 no H581 . C58 . H583 . 108.3 no H582 . C58 . H583 . 111.4 no C54 . C64 . C65 . 119.7(2) yes C54 . C64 . H641 . 119.5 no C65 . C64 . H641 . 120.8 no C64 . C65 . C66 . 121.9(2) yes C64 . C65 . H651 . 119.0 no C66 . C65 . H651 . 119.1 no C65 . C66 . C67 . 117.3(2) yes C65 . C66 . C69 . 123.4(2) yes C67 . C66 . C69 . 119.3(2) yes C66 . C67 . C53 . 122.4(2) yes C66 . C67 . H671 . 117.4 no C53 . C67 . H671 . 120.2 no C66 . C69 . C70 . 126.1(2) yes C66 . C69 . H691 . 116.2 no C70 . C69 . H691 . 117.7 no C69 . C70 . H702 . 120.9 no C69 . C70 . H701 . 121.5 no H702 . C70 . H701 . 117.7 no O7 . C77 . H772 . 106.6 no O7 . C77 . H771 . 109.2 no H772 . C77 . H771 . 110.9 no O7 . C77 . H773 . 109.6 no H772 . C77 . H773 . 108.8 no H771 . C77 . H773 . 111.6 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 C21 . H212 . O55 . 134 0.94 2.55 3.274(3) yes C69 . H691 . O26 1_545 150 0.93 2.57 3.402(3) yes # start Validation Reply Form _vrf_PLAT222_1 ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.34 Ratio RESPONSE: The terminal groups O55 C56 O57 C58 and to a less extend C25 O26 C27 C28 have large displacement parameters indicating some flexibility of the chains ; _vrf_PLAT220_1 ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.34 Ratio RESPONSE: The terminal groups O55 C56 O57 C58 and to a less extend C25 O26 C27 C28 have large displacement parameters indicating some flexibility of the chains ; # end Validation Reply Form data_laebo _database_code_depnum_ccdc_archive 'CCDC 874077' #TrackingRef 'web_deposit_cif_file_0_PeterKundig_1333108873.laebo.cif' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z _cell_length_a 10.5094(6) _cell_length_b 11.6736(7) _cell_length_c 20.6656(14) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2535.31 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z O1 O 0.773823 0.510894 0.62472 O2 O 0.435317 1.05717 0.60717 H28 H 0.447149 1.11964 0.590651 O3 O 0.087073 0.841037 0.698326 O4 O 0.169263 0.753243 0.804902 O5 O 0.838068 0.675067 0.670203 N1 N 0.671844 0.839072 0.791384 C1 C 0.81764 0.606724 0.619855 C2 C 0.857904 0.655366 0.556331 C3 C 0.811259 0.746491 0.524694 C4 C 0.707966 0.824645 0.543651 C5 C 0.706743 0.93662 0.519713 C6 C 0.615099 1.01417 0.538842 H6 H 0.614385 1.08897 0.520729 C7 C 0.523226 0.983623 0.584677 C8 C 0.522092 0.871533 0.609668 C9 C 0.611338 0.793169 0.586637 C10 C 0.433391 0.840549 0.663201 C11 C 0.301682 0.856133 0.65475 C12 C 0.216308 0.828259 0.702768 C13 C 0.261273 0.781878 0.761345 C14 C 0.390797 0.767619 0.770636 C15 C 0.478267 0.797788 0.722195 C16 C 0.039149 0.88589 0.639579 C17 C 0.21032 0.701657 0.863593 H17A H 0.136316 0.685409 0.890947 H17B H 0.267875 0.753968 0.886374 H17C H 0.255078 0.630025 0.853928 C18 C 0.618983 0.779213 0.733595 C19 C 0.635852 0.961665 0.788133 C20 C 0.693311 1.03014 0.843454 C21 C 0.838228 1.02068 0.842987 C22 C 0.877132 0.894705 0.843038 C23 C 0.813173 0.829764 0.786982 C24 C 0.856519 0.704684 0.785505 C25 C 0.792542 0.633266 0.733776 C26 C 0.6495 0.651017 0.736905 H1 H 0.665706 0.80738 0.696854 H2 H 0.421379 0.737848 0.808878 H3 H 0.658507 0.993275 0.744092 H4 H 0.836749 0.863578 0.745459 H5 H 0.623024 0.623036 0.778005 H26 H 0.661957 1.11195 0.83896 H7 H 0.847429 0.850439 0.883668 H8 H 0.837979 0.669683 0.827304 H9 H 0.609594 0.607658 0.702628 H10 H 0.655793 1.00058 0.887292 H11 H 0.870752 1.05453 0.804456 H12 H 0.273979 0.888615 0.612857 H13 H 0.780384 0.963228 0.48905 H14 H 0.063285 0.832304 0.603728 H15 H 0.949541 0.704441 0.780474 H16 H 0.876468 1.05192 0.882658 H27 H 0.54511 0.965358 0.79119 H18 H 0.602524 0.717833 0.60258 H19 H -0.053187 0.892731 0.64551 H20 H 0.809255 0.552887 0.737859 H21 H 0.922554 0.602316 0.536096 H23 H 0.967862 0.882588 0.833498 H24 H 0.070113 0.961492 0.63333 H25 H 0.854663 0.759851 0.481848 O1W O 0.082689 0.726149 0.083668 H2W H 0.031808 0.680027 0.065762 H3W H 0.111565 0.711566 0.123143 O1S O 0.597915 0.421623 0.538074 H1S H 0.64038 0.454828 0.569839 C2S C 0.655726 0.382189 0.48234 H2S1 H 0.719119 0.438091 0.467769 H2S2 H 0.591423 0.371638 0.448517 H2S3 H 0.697653 0.308857 0.491187 #END