# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jean-Noel Volle' _publ_contact_author_email JEAN-NOEL.VOLLE@ENSCM.FR _publ_section_title ; Drug Discovery: Phosphinolactone as Ultimate Bioisostere of the Lactol Group ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? loop_ _publ_author_name 'Jean-Noel Volle' 'Damien Filippini' 'Nikolay Q. Kaloyanov' 'Bartlomiej Krawczyk' 'Tangui Maurice' ; J.-L.Pirat ; 'Arie Van der Le' 'David Virieux' # Attachment 'Compound_8b_revised.cif' data_8b _database_code_depnum_ccdc_archive 'CCDC 733159' #TrackingRef 'Compound_8b_revised.cif' _audit_creation_date 07-04-30 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title jlp4 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.11924(19) _cell_length_b 10.0431(2) _cell_length_c 16.0275(4) _cell_angle_alpha 90 _cell_angle_beta 96.047(2) _cell_angle_gamma 90 _cell_volume 1299.65(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 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 0.0033 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' 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' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 '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' 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 4 # Given Formula = H0.75 # Dc = 0.00 Fooo = 576.00 Mu = 0.00 M = 0.76 # Found Formula = C12 H17 Cl1 N1 O2 P1 # Dc = 1.40 FOOO = 576.00 Mu = 4.07 M = 273.70 _chemical_formula_sum 'C12 H17 Cl1 N1 O2 P1' _chemical_formula_moiety 'C12 H17 Cl1 N1 O2 P1' _chemical_compound_source ? _chemical_formula_weight 273.70 _cell_measurement_reflns_used 17102 _cell_measurement_theta_min 2.9365 _cell_measurement_theta_max 32.2467 _cell_measurement_temperature 173 _exptl_crystal_description prism _exptl_crystal_colour transparent _exptl_crystal_size_min 0.40 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_max 0.55 _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.407 # Sheldrick geometric approximatio 0.82 0.85 _exptl_absorpt_correction_T_min 0.77382 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_detector_area_resol_mean 8.4205 _diffrn_reflns_av_sigmaI/netI 0.0102 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _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 ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2006)' _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 0.0676896863 _diffrn_orient_matrix_UB_12 0.0233840911 _diffrn_orient_matrix_UB_13 -0.0204202668 _diffrn_orient_matrix_UB_21 -0.0555745833 _diffrn_orient_matrix_UB_22 0.0347116049 _diffrn_orient_matrix_UB_23 -0.0294204492 _diffrn_orient_matrix_UB_31 0.0060843412 _diffrn_orient_matrix_UB_32 0.0568681753 _diffrn_orient_matrix_UB_33 0.0263628504 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -54.00 61.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 0.0000 0.0000 0.0000 115 #__ type_ start__ end____ width___ exp.time_ 2 omega -54.00 61.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 90.0000 0.0000 0.0000 115 #__ type_ start__ end____ width___ exp.time_ 3 omega -54.00 61.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 180.0000 0.0000 0.0000 115 #__ type_ start__ end____ width___ exp.time_ 4 omega -54.00 61.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 270.0000 0.0000 0.0000 115 #__ type_ start__ end____ width___ exp.time_ 5 omega -50.00 10.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -25.0000 -80.0000 100.0000 0.0000 0.0000 60 #__ type_ start__ end____ width___ exp.time_ 6 omega -116.00 71.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -25.0000 -10.0000 180.0000 0.0000 0.0000 187 #__ type_ start__ end____ width___ exp.time_ 7 omega -50.00 12.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -25.0000 -80.0000 0.0000 0.0000 0.0000 62 ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count 'every 50 frames' _diffrn_standards_number '2 frames' _diffrn_standards_decay_% 0 _diffrn_ambient_temperature 173 _diffrn_reflns_number 20115 _reflns_number_total 4167 _diffrn_reflns_av_R_equivalents 0.015 # Number of reflections with Friedels Law is 4167 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4634 _diffrn_reflns_theta_min 3.237 _diffrn_reflns_theta_max 32.318 _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 25.532 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.37 _refine_diff_density_max 0.38 _refine_ls_number_reflns 3540 _refine_ls_number_restraints 0 _refine_ls_number_parameters 154 #_refine_ls_R_factor_ref 0.0303 _refine_ls_wR_factor_ref 0.0304 _refine_ls_goodness_of_fit_ref 1.0791 #_reflns_number_all 4167 _refine_ls_R_factor_all 0.0373 _refine_ls_wR_factor_all 0.0336 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3540 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_gt 0.0304 _refine_ls_shift/su_max 0.000981 # 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: 2.36 0.186E-01 1.78 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; 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 ; ? ; # End of 'script/refcif.dat' # 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. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. North, A.C.T., Phillips, D.C. & Mathews, F.S., (1968). Acta Cryst, A24, 351-359. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2002). Xcalibur User Manual. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. 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 _atom_site_attached_hydrogens O1 O 1.07426(9) 0.98164(7) 0.09892(4) 0.0241 1.0000 Uani . . . . . . P2 P 0.90558(3) 0.95537(2) 0.138552(14) 0.0193 1.0000 Uani . . . . . . C3 C 0.97910(11) 0.89176(9) 0.24172(5) 0.0196 1.0000 Uani . . . . . . N4 N 1.10328(9) 0.78937(7) 0.22971(5) 0.0179 1.0000 Uani . . . . . . C5 C 1.25251(10) 0.83322(9) 0.19259(6) 0.0202 1.0000 Uani . . . . . . C6 C 1.19829(12) 0.87743(10) 0.10284(6) 0.0240 1.0000 Uani . . . . . . O7 O 0.80452(10) 1.07814(7) 0.13672(5) 0.0301 1.0000 Uani . . . . . . C8 C 1.36439(13) 0.71174(11) 0.18853(7) 0.0296 1.0000 Uani . . . . . . C9 C 1.34821(13) 0.94519(11) 0.24138(8) 0.0322 1.0000 Uani . . . . . . C10 C 0.84131(13) 0.83368(11) 0.28813(7) 0.0287 1.0000 Uani . . . . . . C11 C 0.79663(10) 0.82434(8) 0.07835(5) 0.0179 1.0000 Uani . . . . . . C12 C 0.65725(11) 0.86195(9) 0.02475(6) 0.0214 1.0000 Uani . . . . . . C13 C 0.57056(11) 0.76903(10) -0.02680(6) 0.0254 1.0000 Uani . . . . . . C14 C 0.61982(11) 0.63619(10) -0.02449(6) 0.0232 1.0000 Uani . . . . . . C15 C 0.75543(10) 0.59893(9) 0.03062(6) 0.0198 1.0000 Uani . . . . . . C16 C 0.84526(10) 0.69056(8) 0.08193(6) 0.0197 1.0000 Uani . . . . . . Cl17 Cl 0.81421(3) 0.43234(2) 0.037274(17) 0.0298 1.0000 Uani . . . . . . H18 H 1.1540 0.8028 0.0712 0.0500 1.0000 Uiso R . . . . . H19 H 1.2890 0.9137 0.0756 0.0500 1.0000 Uiso R . . . . . H20 H 1.1292 0.7443 0.2778 0.0500 1.0000 Uiso R . . . . . H21 H 1.0255 0.9719 0.2723 0.0500 1.0000 Uiso R . . . . . H22 H 0.8874 0.8048 0.3422 0.0500 1.0000 Uiso R . . . . . H23 H 0.7770 0.7614 0.2568 0.0500 1.0000 Uiso R . . . . . H24 H 0.7616 0.8995 0.2958 0.0500 1.0000 Uiso R . . . . . H28 H 1.4602 0.7321 0.1608 0.0500 1.0000 Uiso R . . . . . H29 H 1.3960 0.6834 0.2442 0.0500 1.0000 Uiso R . . . . . H30 H 1.3098 0.6427 0.1539 0.0500 1.0000 Uiso R . . . . . H31 H 0.9360 0.6620 0.1181 0.0500 1.0000 Uiso R . . . . . H32 H 0.6251 0.9525 0.0225 0.0500 1.0000 Uiso R . . . . . H33 H 0.4772 0.7948 -0.0645 0.0500 1.0000 Uiso R . . . . . H34 H 0.5647 0.5710 -0.0592 0.0500 1.0000 Uiso R . . . . . H25 H 1.2865 1.0259 0.2438 0.0500 1.0000 Uiso R . . . . . H26 H 1.4515 0.9656 0.2180 0.0500 1.0000 Uiso R . . . . . H27 H 1.3732 0.9184 0.2998 0.0500 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 0.0267(3) 0.0181(3) 0.0265(3) 0.0075(2) -0.0020(2) -0.0023(2) P2 0.02234(10) 0.01268(9) 0.02137(10) -0.00098(7) -0.00418(7) 0.00198(7) C3 0.0212(4) 0.0185(3) 0.0184(4) -0.0014(3) -0.0012(3) 0.0016(3) N4 0.0185(3) 0.0159(3) 0.0189(3) 0.0027(2) -0.0003(2) 0.0004(2) C5 0.0183(3) 0.0175(3) 0.0242(4) 0.0021(3) -0.0004(3) -0.0013(3) C6 0.0248(4) 0.0239(4) 0.0237(4) 0.0047(3) 0.0047(3) -0.0005(3) O7 0.0361(4) 0.0172(3) 0.0342(4) -0.0045(3) -0.0091(3) 0.0093(3) C8 0.0260(4) 0.0260(4) 0.0376(5) 0.0053(4) 0.0065(4) 0.0070(3) C9 0.0248(4) 0.0271(5) 0.0427(6) -0.0026(4) -0.0058(4) -0.0070(4) C10 0.0255(4) 0.0336(5) 0.0280(4) 0.0005(4) 0.0072(3) 0.0026(4) C11 0.0177(3) 0.0164(3) 0.0190(4) -0.0005(3) -0.0012(3) 0.0004(3) C12 0.0194(3) 0.0212(4) 0.0228(4) 0.0045(3) -0.0021(3) 0.0003(3) C13 0.0205(4) 0.0302(4) 0.0237(4) 0.0048(3) -0.0058(3) -0.0036(3) C14 0.0210(4) 0.0278(4) 0.0199(4) -0.0024(3) -0.0018(3) -0.0062(3) C15 0.0186(3) 0.0188(3) 0.0219(4) -0.0048(3) 0.0014(3) -0.0020(3) C16 0.0189(3) 0.0164(3) 0.0228(4) -0.0033(3) -0.0029(3) 0.0009(3) Cl17 0.02748(11) 0.01904(10) 0.04191(14) -0.01085(8) -0.00111(9) -0.00025(8) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.022(2) 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 . P2 . 1.5913(8) yes O1 . C6 . 1.4491(12) yes P2 . C3 . 1.8140(9) yes P2 . O7 . 1.4796(7) yes P2 . C11 . 1.8071(8) yes C3 . N4 . 1.4669(11) yes C3 . C10 . 1.5233(13) yes C3 . H21 . 0.996 no N4 . C5 . 1.4724(11) yes N4 . H20 . 0.899 no C5 . C6 . 1.5253(13) yes C5 . C8 . 1.5265(13) yes C5 . C9 . 1.5336(13) yes C6 . H18 . 0.954 no C6 . H19 . 0.966 no C8 . H28 . 0.958 no C8 . H29 . 0.947 no C8 . H30 . 0.966 no C9 . H25 . 0.956 no C9 . H26 . 0.976 no C9 . H27 . 0.974 no C10 . H22 . 0.952 no C10 . H23 . 0.998 no C10 . H24 . 0.942 no C11 . C12 . 1.3987(11) yes C11 . C16 . 1.3999(11) yes C12 . C13 . 1.3879(13) yes C12 . H32 . 0.945 no C13 . C14 . 1.3921(14) yes C13 . H33 . 0.954 no C14 . C15 . 1.3885(12) yes C14 . H34 . 0.942 no C15 . C16 . 1.3887(11) yes C15 . Cl17 . 1.7400(9) yes C16 . H31 . 0.933 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 P2 . O1 . C6 . 119.10(6) yes O1 . P2 . C3 . 102.00(4) yes O1 . P2 . O7 . 110.66(4) yes C3 . P2 . O7 . 116.11(4) yes O1 . P2 . C11 . 107.52(4) yes C3 . P2 . C11 . 109.01(4) yes O7 . P2 . C11 . 110.91(4) yes P2 . C3 . N4 . 106.98(6) yes P2 . C3 . C10 . 113.07(6) yes N4 . C3 . C10 . 110.24(7) yes P2 . C3 . H21 . 103.6 no N4 . C3 . H21 . 113.7 no C10 . C3 . H21 . 109.1 no C3 . N4 . C5 . 116.72(7) yes C3 . N4 . H20 . 110.0 no C5 . N4 . H20 . 111.6 no N4 . C5 . C6 . 107.46(7) yes N4 . C5 . C8 . 107.27(7) yes C6 . C5 . C8 . 107.84(8) yes N4 . C5 . C9 . 114.05(8) yes C6 . C5 . C9 . 110.35(8) yes C8 . C5 . C9 . 109.63(8) yes C5 . C6 . O1 . 112.42(8) yes C5 . C6 . H18 . 109.1 no O1 . C6 . H18 . 108.9 no C5 . C6 . H19 . 112.2 no O1 . C6 . H19 . 105.5 no H18 . C6 . H19 . 108.6 no C5 . C8 . H28 . 111.4 no C5 . C8 . H29 . 107.7 no H28 . C8 . H29 . 110.5 no C5 . C8 . H30 . 111.0 no H28 . C8 . H30 . 103.4 no H29 . C8 . H30 . 112.9 no C5 . C9 . H25 . 113.8 no C5 . C9 . H26 . 111.6 no H25 . C9 . H26 . 108.2 no C5 . C9 . H27 . 109.3 no H25 . C9 . H27 . 104.6 no H26 . C9 . H27 . 109.0 no C3 . C10 . H22 . 108.8 no C3 . C10 . H23 . 113.9 no H22 . C10 . H23 . 111.8 no C3 . C10 . H24 . 110.2 no H22 . C10 . H24 . 107.7 no H23 . C10 . H24 . 104.2 no P2 . C11 . C12 . 116.76(6) yes P2 . C11 . C16 . 123.85(6) yes C12 . C11 . C16 . 119.39(8) yes C11 . C12 . C13 . 120.72(8) yes C11 . C12 . H32 . 119.0 no C13 . C12 . H32 . 120.2 no C12 . C13 . C14 . 120.15(8) yes C12 . C13 . H33 . 121.0 no C14 . C13 . H33 . 118.9 no C13 . C14 . C15 . 118.78(8) yes C13 . C14 . H34 . 122.2 no C15 . C14 . H34 . 119.0 no C14 . C15 . C16 . 122.00(8) yes C14 . C15 . Cl17 . 119.48(7) yes C16 . C15 . Cl17 . 118.51(7) yes C11 . C16 . C15 . 118.91(8) yes C11 . C16 . H31 . 121.5 no C15 . C16 . H31 . 119.6 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 N4 . H20 . O7 3_745 160 0.90 2.19 3.051(2) yes # Attachment 'Compound_5a_revised.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 733160' #TrackingRef 'Compound_5a_revised.cif' _audit_creation_date 07-04-27 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'CRYSTALS_cP 1 21/a 1 R = New: P21/c' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 13.4636(10) _cell_length_b 8.4643(4) _cell_length_c 12.3030(9) _cell_angle_alpha 90 _cell_angle_beta 113.455(9) _cell_angle_gamma 90 _cell_volume 1286.20(17) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 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 0.0033 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' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C48 H72 N4 O8 P4 # Dc = 1.24 Fooo = 512.00 Mu = 2.00 M = 239.25 # Found Formula = C48 H72 N4 O8 P4 # Dc = 1.24 FOOO = 512.00 Mu = 2.00 M = 239.25 _chemical_formula_sum 'C12 H18 N O2 P' _chemical_formula_moiety 'C12 H18 N O2 P' _chemical_compound_source ? _chemical_formula_weight 239.24 _cell_measurement_reflns_used 4465 _cell_measurement_theta_min 2.8802 _cell_measurement_theta_max 32.3851 _exptl_absorpt_correction_T_min 0.64622 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 8.4205 _diffrn_reflns_av_sigmaI/netI 0.1362 _cell_measurement_temperature 173 _exptl_crystal_description prism _exptl_crystal_colour transparent _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.25 _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.200 # Sheldrick geometric approximatio 0.96 0.98 # No experimental values of Tmin/max available _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) ; _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2006)' _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 0.0515765697 _diffrn_orient_matrix_UB_12 -0.0477532414 _diffrn_orient_matrix_UB_13 0.0223226696 _diffrn_orient_matrix_UB_21 0.0235912072 _diffrn_orient_matrix_UB_22 0.0523443685 _diffrn_orient_matrix_UB_23 0.0447484131 _diffrn_orient_matrix_UB_31 -0.0271552935 _diffrn_orient_matrix_UB_32 -0.0450642814 _diffrn_orient_matrix_UB_33 0.0282496258 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -54.00 61.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 0.0000 0.0000 0.0000 115 #__ type_ start__ end____ width___ exp.time_ 2 omega -54.00 61.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 90.0000 0.0000 0.0000 115 #__ type_ start__ end____ width___ exp.time_ 3 omega -54.00 61.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 180.0000 0.0000 0.0000 115 #__ type_ start__ end____ width___ exp.time_ 4 omega -54.00 61.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 270.0000 0.0000 0.0000 115 #__ type_ start__ end____ width___ exp.time_ 5 omega -50.00 10.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -25.0000 -80.0000 100.0000 0.0000 0.0000 60 #__ type_ start__ end____ width___ exp.time_ 6 omega -116.00 71.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -25.0000 -10.0000 180.0000 0.0000 0.0000 187 #__ type_ start__ end____ width___ exp.time_ 7 omega -50.00 12.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -25.0000 -80.0000 0.0000 0.0000 0.0000 62 ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count 'every 50 frames' _diffrn_standards_number '2 frames' _diffrn_standards_decay_% 0 _diffrn_ambient_temperature 173 _diffrn_reflns_number 21989 _reflns_number_total 4232 _diffrn_reflns_av_R_equivalents 0.064 # Number of reflections with Friedels Law is 4232 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4495 _diffrn_reflns_theta_min 2.917 _diffrn_reflns_theta_max 32.445 _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 30.174 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -19 _reflns_limit_h_max 18 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.22 _refine_diff_density_max 0.26 _refine_ls_number_reflns 1451 _refine_ls_number_restraints 0 _refine_ls_number_parameters 145 #_refine_ls_R_factor_ref 0.0266 _refine_ls_wR_factor_ref 0.0274 _refine_ls_goodness_of_fit_ref 1.1304 #_reflns_number_all 4232 _refine_ls_R_factor_all 0.1011 _refine_ls_wR_factor_all 0.0278 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1451 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_gt 0.0274 _refine_ls_shift/su_max 0.000351 # 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: 12.7 -18.9 10.9 -3.82 ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; 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 ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. North, A.C.T., Phillips, D.C. & Mathews, F.S., (1968). Acta Cryst, A24, 351-359. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2002). Xcalibur User Manual. 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 _atom_site_attached_hydrogens O1 O 0.13704(11) -0.06875(19) 0.48982(11) 0.0261 1.0000 Uani . . . . . . P2 P 0.26486(4) -0.08360(7) 0.52851(4) 0.0205 1.0000 Uani . . . . . . C3 C 0.30981(16) -0.1342(2) 0.68423(16) 0.0215 1.0000 Uani . . . . . . N4 N 0.24248(14) -0.2656(2) 0.69285(14) 0.0230 1.0000 Uani . . . . . . C5 C 0.12512(17) -0.2333(3) 0.64958(17) 0.0257 1.0000 Uani . . . . . . C6 C 0.08329(17) -0.2026(3) 0.51687(18) 0.0288 1.0000 Uani . . . . . . O7 O 0.29960(12) -0.19552(18) 0.45873(12) 0.0283 1.0000 Uani . . . . . . C8 C 0.42797(18) -0.1840(3) 0.7366(2) 0.0363 1.0000 Uani . . . . . . C9 C 0.09751(18) -0.0959(3) 0.71304(19) 0.0382 1.0000 Uani . . . . . . C10 C 0.0713(2) -0.3849(3) 0.6663(2) 0.0432 1.0000 Uani . . . . . . C11 C 0.29971(16) 0.1169(2) 0.51268(16) 0.0231 1.0000 Uani . . . . . . C12 C 0.35948(19) 0.1468(3) 0.44551(19) 0.0313 1.0000 Uani . . . . . . C13 C 0.3842(2) 0.3016(3) 0.4278(2) 0.0377 1.0000 Uani . . . . . . C14 C 0.35031(18) 0.4249(3) 0.47688(19) 0.0345 1.0000 Uani . . . . . . C15 C 0.29204(18) 0.3968(3) 0.5456(2) 0.0344 1.0000 Uani . . . . . . C16 C 0.26697(19) 0.2429(3) 0.5630(2) 0.0307 1.0000 Uani . . . . . . H17 H 0.2636 -0.2918 0.7711 0.0500 1.0000 Uiso R . . . . . H18 H 0.4495 -0.2091 0.8189 0.0500 1.0000 Uiso R . . . . . H19 H 0.4729 -0.1005 0.7290 0.0500 1.0000 Uiso R . . . . . H20 H 0.4370 -0.2760 0.6959 0.0500 1.0000 Uiso R . . . . . H21 H 0.2995 -0.0419 0.7265 0.0500 1.0000 Uiso R . . . . . H22 H 0.0952 -0.2958 0.4766 0.0500 1.0000 Uiso R . . . . . H23 H 0.0063 -0.1796 0.4867 0.0500 1.0000 Uiso R . . . . . H24 H 0.1238 0.0031 0.6963 0.0500 1.0000 Uiso R . . . . . H25 H 0.0202 -0.0890 0.6879 0.0500 1.0000 Uiso R . . . . . H26 H 0.1292 -0.1151 0.7975 0.0500 1.0000 Uiso R . . . . . H27 H -0.0063 -0.3716 0.6347 0.0500 1.0000 Uiso R . . . . . H28 H 0.0968 -0.4091 0.7492 0.0500 1.0000 Uiso R . . . . . H29 H 0.0885 -0.4719 0.6261 0.0500 1.0000 Uiso R . . . . . H30 H 0.2284 0.2231 0.6098 0.0500 1.0000 Uiso R . . . . . H31 H 0.2709 0.4806 0.5807 0.0500 1.0000 Uiso R . . . . . H32 H 0.3658 0.5284 0.4639 0.0500 1.0000 Uiso R . . . . . H33 H 0.4243 0.3212 0.3827 0.0500 1.0000 Uiso R . . . . . H34 H 0.3827 0.0632 0.4125 0.0500 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 0.0246(7) 0.0317(8) 0.0191(6) 0.0059(6) 0.0057(5) 0.0002(7) P2 0.0258(2) 0.0202(2) 0.0161(2) -0.0003(3) 0.00917(18) 0.0002(3) C3 0.0242(10) 0.0232(10) 0.0164(8) -0.0013(7) 0.0074(7) 0.0026(8) N4 0.0267(9) 0.0257(9) 0.0184(7) 0.0035(7) 0.0110(7) 0.0023(7) C5 0.0242(10) 0.0345(12) 0.0202(9) 0.0039(9) 0.0109(8) 0.0010(9) C6 0.0244(10) 0.0388(12) 0.0211(9) 0.0042(9) 0.0068(8) -0.0061(10) O7 0.0418(9) 0.0223(8) 0.0239(7) -0.0030(6) 0.0164(7) 0.0002(7) C8 0.0254(11) 0.0485(15) 0.0306(11) 0.0063(10) 0.0065(9) 0.0033(11) C9 0.0343(12) 0.0543(15) 0.0301(10) 0.0045(12) 0.0173(9) 0.0144(13) C10 0.0384(13) 0.0568(19) 0.0348(12) 0.0118(11) 0.0150(10) -0.0120(12) C11 0.0272(10) 0.0192(11) 0.0211(9) 0.0003(7) 0.0078(8) 0.0014(8) C12 0.0414(14) 0.0261(11) 0.0326(11) 0.0029(10) 0.0214(10) 0.0036(10) C13 0.0494(15) 0.0324(13) 0.0412(13) 0.0078(11) 0.0283(12) -0.0018(12) C14 0.0380(12) 0.0225(11) 0.0378(11) 0.0043(11) 0.0096(9) -0.0014(12) C15 0.0374(13) 0.0241(12) 0.0402(12) -0.0042(10) 0.0139(10) 0.0050(10) C16 0.0322(12) 0.0283(12) 0.0362(11) -0.0030(10) 0.0186(9) 0.0027(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.376(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 . P2 . 1.5975(15) yes O1 . C6 . 1.452(3) yes P2 . C3 . 1.8158(19) yes P2 . O7 . 1.4741(15) yes P2 . C11 . 1.792(2) yes C3 . N4 . 1.465(3) yes C3 . C8 . 1.519(3) yes C3 . H21 . 0.979 no N4 . C5 . 1.478(3) yes N4 . H17 . 0.915 no C5 . C6 . 1.523(3) yes C5 . C9 . 1.527(3) yes C5 . C10 . 1.527(3) yes C6 . H22 . 0.978 no C6 . H23 . 0.972 no C8 . H18 . 0.959 no C8 . H19 . 0.959 no C8 . H20 . 0.960 no C9 . H24 . 0.963 no C9 . H25 . 0.962 no C9 . H26 . 0.967 no C10 . H27 . 0.965 no C10 . H28 . 0.960 no C10 . H29 . 0.965 no C11 . C12 . 1.387(3) yes C11 . C16 . 1.390(3) yes C12 . C13 . 1.390(3) yes C12 . H34 . 0.930 no C13 . C14 . 1.372(3) yes C13 . H33 . 0.930 no C14 . C15 . 1.384(3) yes C14 . H32 . 0.929 no C15 . C16 . 1.384(3) yes C15 . H31 . 0.932 no C16 . H30 . 0.931 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 P2 . O1 . C6 . 116.51(13) yes O1 . P2 . C3 . 101.54(8) yes O1 . P2 . O7 . 115.53(9) yes C3 . P2 . O7 . 114.40(9) yes O1 . P2 . C11 . 101.00(9) yes C3 . P2 . C11 . 110.27(9) yes O7 . P2 . C11 . 112.82(9) yes P2 . C3 . N4 . 107.43(12) yes P2 . C3 . C8 . 111.47(14) yes N4 . C3 . C8 . 109.40(17) yes P2 . C3 . H21 . 108.3 no N4 . C3 . H21 . 110.1 no C8 . C3 . H21 . 110.1 no C3 . N4 . C5 . 115.93(16) yes C3 . N4 . H17 . 108.5 no C5 . N4 . H17 . 105.3 no N4 . C5 . C6 . 107.69(16) yes N4 . C5 . C9 . 113.54(18) yes C6 . C5 . C9 . 110.88(18) yes N4 . C5 . C10 . 107.05(18) yes C6 . C5 . C10 . 107.18(18) yes C9 . C5 . C10 . 110.23(19) yes C5 . C6 . O1 . 111.95(16) yes C5 . C6 . H22 . 109.9 no O1 . C6 . H22 . 108.4 no C5 . C6 . H23 . 109.1 no O1 . C6 . H23 . 108.0 no H22 . C6 . H23 . 109.5 no C3 . C8 . H18 . 109.6 no C3 . C8 . H19 . 110.4 no H18 . C8 . H19 . 109.2 no C3 . C8 . H20 . 109.5 no H18 . C8 . H20 . 108.8 no H19 . C8 . H20 . 109.3 no C5 . C9 . H24 . 111.6 no C5 . C9 . H25 . 109.5 no H24 . C9 . H25 . 108.7 no C5 . C9 . H26 . 109.2 no H24 . C9 . H26 . 109.5 no H25 . C9 . H26 . 108.3 no C5 . C10 . H27 . 110.1 no C5 . C10 . H28 . 109.5 no H27 . C10 . H28 . 109.0 no C5 . C10 . H29 . 110.4 no H27 . C10 . H29 . 108.9 no H28 . C10 . H29 . 108.9 no P2 . C11 . C12 . 118.49(16) yes P2 . C11 . C16 . 122.33(16) yes C12 . C11 . C16 . 119.2(2) yes C11 . C12 . C13 . 119.8(2) yes C11 . C12 . H34 . 119.8 no C13 . C12 . H34 . 120.4 no C12 . C13 . C14 . 120.4(2) yes C12 . C13 . H33 . 119.6 no C14 . C13 . H33 . 120.0 no C13 . C14 . C15 . 120.5(2) yes C13 . C14 . H32 . 120.3 no C15 . C14 . H32 . 119.2 no C14 . C15 . C16 . 119.3(2) yes C14 . C15 . H31 . 120.3 no C16 . C15 . H31 . 120.4 no C11 . C16 . C15 . 120.9(2) yes C11 . C16 . H30 . 119.4 no C15 . C16 . H30 . 119.7 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 N4 . H17 . O7 4_545 168 0.92 2.16 3.066(2) yes data_1 _database_code_depnum_ccdc_archive 'CCDC 733161' #TrackingRef 'Compound_5b_revised.cif' _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; No particular problems with this structure 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 ; ? ; _cell_length_a 13.4738(6) _cell_length_b 8.3372(4) _cell_length_c 12.4129(6) _cell_angle_alpha 90 _cell_angle_beta 92.615(4) _cell_angle_gamma 90 _cell_volume 1392.93(11) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x,-y+1/2,z+1/2 -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 0.0033 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' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 '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' _cell_formula_units_Z 4 _chemical_formula_sum 'C12 H17 Cl N O2 P' _chemical_formula_moiety 'C12 H17 Cl N O2 P' _chemical_compound_source ? _chemical_formula_weight 273.69 _cell_measurement_reflns_used 3009 _cell_measurement_theta_min 4.0877 _cell_measurement_theta_max 28.9217 _cell_measurement_temperature 173 _exptl_crystal_description block _exptl_crystal_colour 'white transparent' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.25 _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.379 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_T_min 0.58190 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_measurement_method \w _diffrn_measurement_device CCD _diffrn_radiation_monochromator graphite _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type ; Goniometer Xcalibur, detector: Sapphire3 (Gemini Mo) ; _diffrn_detector_area_resol_mean 16.0143 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_orient_matrix_UB_11 0.0151870733 _diffrn_orient_matrix_UB_12 0.0795418201 _diffrn_orient_matrix_UB_13 -0.0126856794 _diffrn_orient_matrix_UB_21 0.0418666904 _diffrn_orient_matrix_UB_22 -0.0018021388 _diffrn_orient_matrix_UB_23 0.0378030426 _diffrn_orient_matrix_UB_31 0.0361538230 _diffrn_orient_matrix_UB_32 -0.0312173488 _diffrn_orient_matrix_UB_33 -0.0345943876 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 34.00 83.00 1.0000 110.0000 omega____ theta____ kappa____ phi______ frames - 18.0193 179.0000 330.0000 49 #__ type_ start__ end____ width___ exp.time_ 2 omega 5.00 90.00 1.0000 110.0000 omega____ theta____ kappa____ phi______ frames - 18.0193 38.0000 120.0000 85 #__ type_ start__ end____ width___ exp.time_ 3 omega -47.00 36.00 1.0000 110.0000 omega____ theta____ kappa____ phi______ frames - 18.0193 -38.0000 330.0000 83 #__ type_ start__ end____ width___ exp.time_ 4 omega -49.00 -22.00 1.0000 110.0000 omega____ theta____ kappa____ phi______ frames - -18.7224 77.0000 330.0000 27 ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _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 173 _diffrn_reflns_number 6357 _reflns_number_total 3150 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections with Friedels Law is 3150 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3691 _diffrn_reflns_theta_min 4.096 _diffrn_reflns_theta_max 28.998 _diffrn_measured_fraction_theta_max 0.850 _diffrn_reflns_theta_full 25.228 _diffrn_measured_fraction_theta_full 0.987 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -17 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _oxford_diffrn_Wilson_B_factor 1.67 _oxford_diffrn_Wilson_scale 0.06 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.34 _refine_diff_density_max 0.56 # 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>2.0\s(I) _refine_ls_number_reflns 2199 _refine_ls_number_restraints 0 _refine_ls_number_parameters 154 _oxford_refine_ls_R_factor_ref 0.0432 _refine_ls_wR_factor_ref 0.0465 _refine_ls_goodness_of_fit_ref 1.0943 _refine_ls_shift/su_max 0.000356 # The values computed from all data _oxford_reflns_number_all 3150 _refine_ls_R_factor_all 0.0715 _refine_ls_wR_factor_all 0.0508 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2199 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_gt 0.0465 # 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: 34.2 -45.2 28.7 -7.95 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference User-defined data collection reference User defined data reduction User defined cell refinement Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. 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 Cl1 Cl 0.45340(5) 1.29991(9) 0.17014(6) 0.0382 1.0000 Uani . . . . . . . C2 C 0.37419(16) 1.2787(3) 0.27672(19) 0.0249 1.0000 Uani . . . . . . . C3 C 0.34429(16) 1.1245(3) 0.30359(18) 0.0216 1.0000 Uani . . . . . . . C4 C 0.28181(16) 1.1064(3) 0.38938(17) 0.0206 1.0000 Uani . . . . . . . P5 P 0.24469(4) 0.90543(7) 0.42121(4) 0.0176 1.0000 Uani . . . . . . . O6 O 0.27200(12) 0.78760(19) 0.33856(12) 0.0240 1.0000 Uani . . . . . . . O7 O 0.12802(11) 0.9304(2) 0.43447(12) 0.0237 1.0000 Uani . . . . . . . C8 C 0.07622(16) 0.7981(3) 0.48369(19) 0.0260 1.0000 Uani . . . . . . . C9 C 0.11574(17) 0.7665(3) 0.59917(18) 0.0258 1.0000 Uani . . . . . . . N10 N 0.22269(14) 0.7263(2) 0.59489(15) 0.0208 1.0000 Uani . . . . . . . C11 C 0.28744(15) 0.8539(3) 0.55792(16) 0.0185 1.0000 Uani . . . . . . . C12 C 0.39476(17) 0.7957(3) 0.5626(2) 0.0275 1.0000 Uani . . . . . . . H13 H 0.4146 0.7692 0.6364 0.0445 1.0000 Uiso R . . . . . . H14 H 0.4360 0.8790 0.5372 0.0452 1.0000 Uiso R . . . . . . H15 H 0.4001 0.7008 0.5177 0.0453 1.0000 Uiso R . . . . . . H16 H 0.2830 0.9509 0.6028 0.0241 1.0000 Uiso R . . . . . . H17 H 0.2454 0.6612 0.6398 0.0289 1.0000 Uiso R . . . . . . C18 C 0.0637(2) 0.6165(4) 0.6390(2) 0.0415 1.0000 Uani . . . . . . . H19 H 0.0874 0.5937 0.7119 0.0667 1.0000 Uiso R . . . . . . H20 H -0.0073 0.6357 0.6381 0.0666 1.0000 Uiso R . . . . . . H21 H 0.0764 0.5260 0.5919 0.0670 1.0000 Uiso R . . . . . . C22 C 0.09547(19) 0.9098(4) 0.6720(2) 0.0363 1.0000 Uani . . . . . . . H23 H 0.1256 0.8901 0.7427 0.0580 1.0000 Uiso R . . . . . . H24 H 0.1226 1.0055 0.6420 0.0582 1.0000 Uiso R . . . . . . H25 H 0.0243 0.9221 0.6771 0.0579 1.0000 Uiso R . . . . . . H26 H 0.0056 0.8257 0.4835 0.0343 1.0000 Uiso R . . . . . . H27 H 0.0848 0.7012 0.4407 0.0341 1.0000 Uiso R . . . . . . C28 C 0.25158(19) 1.2401(3) 0.4463(2) 0.0305 1.0000 Uani . . . . . . . C29 C 0.2815(2) 1.3924(3) 0.4170(2) 0.0350 1.0000 Uani . . . . . . . C30 C 0.34385(19) 1.4126(3) 0.3315(2) 0.0311 1.0000 Uani . . . . . . . H31 H 0.3652 1.5158 0.3119 0.0383 1.0000 Uiso R . . . . . . H32 H 0.2643 1.4812 0.4580 0.0443 1.0000 Uiso R . . . . . . H33 H 0.2077 1.2272 0.5044 0.0381 1.0000 Uiso R . . . . . . H34 H 0.3645 1.0331 0.2646 0.0296 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 0.0331(3) 0.0427(4) 0.0394(3) 0.0149(3) 0.0093(3) -0.0038(3) C2 0.0175(10) 0.0299(12) 0.0271(11) 0.0084(10) -0.0022(8) -0.0008(9) C3 0.0188(10) 0.0209(11) 0.0250(10) 0.0045(8) -0.0006(8) -0.0005(8) C4 0.0203(10) 0.0182(10) 0.0230(10) 0.0012(8) -0.0021(8) -0.0022(9) P5 0.0179(2) 0.0193(3) 0.0154(2) 0.0004(2) -0.00052(18) -0.0013(2) O6 0.0308(8) 0.0219(8) 0.0193(7) -0.0011(6) 0.0015(6) -0.0025(7) O7 0.0171(7) 0.0318(9) 0.0220(7) 0.0059(7) -0.0028(6) -0.0007(7) C8 0.0181(10) 0.0355(13) 0.0242(11) 0.0051(10) 0.0001(8) -0.0059(10) C9 0.0193(10) 0.0380(14) 0.0202(11) 0.0052(10) 0.0027(8) -0.0008(10) N10 0.0206(9) 0.0244(10) 0.0172(8) 0.0062(7) -0.0004(7) 0.0002(8) C11 0.0191(10) 0.0232(10) 0.0130(9) -0.0013(8) -0.0027(7) 0.0005(8) C12 0.0202(10) 0.0355(13) 0.0266(11) 0.0018(10) -0.0011(9) 0.0041(10) C18 0.0316(13) 0.059(2) 0.0342(13) 0.0166(13) 0.0002(11) -0.0153(13) C22 0.0279(12) 0.0564(17) 0.0249(12) -0.0018(13) 0.0035(9) 0.0147(13) C28 0.0332(13) 0.0274(12) 0.0311(13) -0.0005(10) 0.0044(10) 0.0026(11) C29 0.0402(14) 0.0210(12) 0.0438(15) -0.0058(11) 0.0016(11) 0.0049(11) C30 0.0319(12) 0.0191(11) 0.0418(14) 0.0056(11) -0.0035(10) -0.0040(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 5.297(11) 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 Cl1 . C2 . 1.746(2) yes C2 . C3 . 1.392(3) yes C2 . C30 . 1.379(4) yes C3 . C4 . 1.396(3) yes C3 . H34 . 0.949 no C4 . P5 . 1.797(2) yes C4 . C28 . 1.391(3) yes P5 . O6 . 1.4789(17) yes P5 . O7 . 1.6016(16) yes P5 . C11 . 1.819(2) yes O7 . C8 . 1.455(3) yes C8 . C9 . 1.529(3) yes C8 . H26 . 0.979 no C8 . H27 . 0.977 no C9 . N10 . 1.483(3) yes C9 . C18 . 1.527(4) yes C9 . C22 . 1.530(4) yes N10 . C11 . 1.463(3) yes N10 . H17 . 0.827 no C11 . C12 . 1.524(3) yes C11 . H16 . 0.985 no C12 . H13 . 0.969 no C12 . H14 . 0.953 no C12 . H15 . 0.971 no C18 . H19 . 0.966 no C18 . H20 . 0.970 no C18 . H21 . 0.974 no C22 . H23 . 0.964 no C22 . H24 . 0.960 no C22 . H25 . 0.969 no C28 . C29 . 1.385(4) yes C28 . H33 . 0.960 no C29 . C30 . 1.393(4) yes C29 . H32 . 0.934 no C30 . H31 . 0.942 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 Cl1 . C2 . C3 . 117.95(19) yes Cl1 . C2 . C30 . 119.78(19) yes C3 . C2 . C30 . 122.3(2) yes C2 . C3 . C4 . 118.3(2) yes C2 . C3 . H34 . 121.7 no C4 . C3 . H34 . 120.0 no C3 . C4 . P5 . 116.90(17) yes C3 . C4 . C28 . 120.1(2) yes P5 . C4 . C28 . 123.02(18) yes C4 . P5 . O6 . 112.72(10) yes C4 . P5 . O7 . 100.71(10) yes O6 . P5 . O7 . 115.71(9) yes C4 . P5 . C11 . 110.24(10) yes O6 . P5 . C11 . 114.33(10) yes O7 . P5 . C11 . 101.85(9) yes P5 . O7 . C8 . 115.90(14) yes O7 . C8 . C9 . 111.78(18) yes O7 . C8 . H26 . 107.8 no C9 . C8 . H26 . 109.9 no O7 . C8 . H27 . 109.0 no C9 . C8 . H27 . 108.9 no H26 . C8 . H27 . 109.4 no C8 . C9 . N10 . 107.62(18) yes C8 . C9 . C18 . 107.4(2) yes N10 . C9 . C18 . 106.8(2) yes C8 . C9 . C22 . 110.8(2) yes N10 . C9 . C22 . 113.4(2) yes C18 . C9 . C22 . 110.5(2) yes C9 . N10 . C11 . 116.22(18) yes C9 . N10 . H17 . 117.1 no C11 . N10 . H17 . 118.8 no N10 . C11 . P5 . 107.26(14) yes N10 . C11 . C12 . 109.59(19) yes P5 . C11 . C12 . 111.73(15) yes N10 . C11 . H16 . 111.5 no P5 . C11 . H16 . 108.0 no C12 . C11 . H16 . 108.8 no C11 . C12 . H13 . 109.2 no C11 . C12 . H14 . 108.8 no H13 . C12 . H14 . 109.8 no C11 . C12 . H15 . 109.4 no H13 . C12 . H15 . 109.4 no H14 . C12 . H15 . 110.2 no C9 . C18 . H19 . 109.1 no C9 . C18 . H20 . 109.2 no H19 . C18 . H20 . 109.1 no C9 . C18 . H21 . 110.2 no H19 . C18 . H21 . 110.5 no H20 . C18 . H21 . 108.7 no C9 . C22 . H23 . 109.0 no C9 . C22 . H24 . 109.7 no H23 . C22 . H24 . 110.0 no C9 . C22 . H25 . 108.9 no H23 . C22 . H25 . 109.6 no H24 . C22 . H25 . 109.5 no C4 . C28 . C29 . 120.4(2) yes C4 . C28 . H33 . 119.8 no C29 . C28 . H33 . 119.8 no C28 . C29 . C30 . 120.2(2) yes C28 . C29 . H32 . 120.1 no C30 . C29 . H32 . 119.5 no C29 . C30 . C2 . 118.7(2) yes C29 . C30 . H31 . 120.6 no C2 . C30 . H31 . 120.7 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 N10 . H17 . O6 3_565 126 0.83 2.51 3.069(4) yes