# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Francesca Fabbiani' 'Gernot Buth' 'Werner Kuhs' 'Demi Levendis' 'Norman Shankland' 'Heidrun Sowa' _publ_contact_author_name 'Francesca Fabbiani' _publ_contact_author_email FFABBIA@GWDG.DE _publ_section_title ; Searching for novel crystal forms by in situ high-pressure crystallisation: the example of gabapentin heptahydrate ; # Attachment 'gabapentin_heptahydrate.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 755780' #TrackingRef 'gabapentin_heptahydrate.cif' #Gabapentin heptahydrate _refine_special_details ; All H-atoms were found on Fourier difference maps, then refined subject to geometrical restraints and finally allowed to ride on the parent atoms. after optimising their positions to give reasonable geometries. The program CRYSTALS allows initial refinement of H-atom positions using the X-ray data and solft restraints on bond angles and lengths to relularise their geometry. H-Uiso were assigned in the range 1.2-1.5 times Ueq of the parent atom The Following ALERTS were generated by PLATON checkcif<<< PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.52 PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 25.24 Deg PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.57 ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.610 0.980 Tmin(prime) and Tmax expected: 0.971 0.977 RR(prime) = 0.626 Please check that your absorption correction is appropriate. PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 100 These alerts are not uncommon for high-pressure data. The geometry of the diamond-anvil cell severely restricts the amount of recirpocal space that can be accessed, resulting in a poor completeness. This is more evident for lower-symmetry crystal systems (triclinic in this case). A total of four data sets were collected: two data sets were collected on crystal A with the pressure cell glued on two different orientations on the goniometer head to similate two values of chi and improve data completeness. Two furtherdata sets were similarly collected for crystal B grown under the same experimental conditions. The orientation of crystal B was very different from that of crystal A. The larger than expected range of transmission is probably due to the absorption effects of the high-pressure cell. The use of thermal vibration and similarity restraints, 100 in total, for refinement of non-H atoms ADPs, increases the data to parameter ratio to 9.4. Resolution and completeness are given below: Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 21.10 0.500 0.711 1543 1097 446 23.33 0.550 0.656 2054 1347 707 25.59 0.600 0.568 2663 1513 1150 #----------------------------------------------------------- ACTA Min. Res. ---- 26.57 0.621 0.516 2973 1533 1440 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 8 H2 O Noted, no action taken. ABSMU_01 Radiation type not identified. Calculation of _exptl_absorpt_correction_mu not performed. PLAT092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.72 Ang. Synchrotron radiation was used. 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K Data were collected at room temperature ; _cell_length_a 6.7906(12) _cell_length_b 7.3159(4) _cell_length_c 15.8428(14) _cell_angle_alpha 86.297(6) _cell_angle_beta 78.924(11) _cell_angle_gamma 72.713(6) _cell_volume 737.49(16) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' 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' 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 = C7 H4 N2 O8 # Dc = 1.10 Fooo = 328.00 Mu = 1.04 M = 244.12 # Found Formula = C9 H31 N1 O9 # Dc = 1.34 FOOO = 328.00 Mu = 1.18 M = 297.35 _chemical_formula_sum 'C9 H31 N1 O9' _chemical_formula_moiety 'C9 H17 N O2, 7(H2 O) ' _chemical_compound_source ; The compound was used as received from Sigma-Aldrich ; _exptl_crystal_preparation ; High-pressure crystallisation of aqueous solution at 0.8 GPa. Single-crystal data collected at 0.9 GPa ; _chemical_formula_weight 297.35 _cell_measurement_reflns_used 1722 _cell_measurement_theta_min 3 _cell_measurement_theta_max 26 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.25 _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'based on symmetry-related measuraments' # SHADE (Parsons, 2004) # SADABS (Siemens, 1996) # The following data are from Sadabs: _exptl_absorpt_correction_T_min 0.61 _exptl_absorpt_correction_T_max 0.98 # Sheldrick geometric approximatio 0.98 0.98 _diffrn_measurement_device 'Bruker AXS SMART APEX' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.72000 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution SIR92 _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003), PLATON, XCIF, ENCIFER' _computing_molecular_graphics MERCURY _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_reflns_number 6429 _reflns_number_total 1533 _diffrn_reflns_av_R_equivalents 0.052 # Number of reflections with Friedels Law is 1533 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2964 _diffrn_reflns_theta_min 2.654 _diffrn_reflns_theta_max 26.573 _diffrn_measured_fraction_theta_max 0.516 _diffrn_reflns_theta_full 25.244 _diffrn_measured_fraction_theta_full 0.573 _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #_diffrn_reflns_limit_h_max 6 #_diffrn_reflns_limit_h_min -7 #_diffrn_reflns_limit_k_max 8 #_diffrn_reflns_limit_k_min -8 #_diffrn_reflns_limit_l_max 18 #_diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min -8 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 2.59 _oxford_diffrn_Wilson_scale 0.49 _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.21 _refine_diff_density_max 0.19 # 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 1523 _refine_ls_number_restraints 100 _refine_ls_number_parameters 172 _oxford_refine_ls_R_factor_ref 0.0528 _refine_ls_wR_factor_ref 0.1310 _refine_ls_goodness_of_fit_ref 0.9522 _refine_ls_shift/su_max 0.000126 # The values computed from all data _oxford_reflns_number_all 1523 _refine_ls_R_factor_all 0.0528 _refine_ls_wR_factor_all 0.1310 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1294 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_gt 0.1268 # 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 constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.09P)^2^ + 0.27P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. ; # 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 C1 C 0.1948(4) 0.7950(3) 0.23288(15) 0.0242 1.0000 Uani . U . . . . . C2 C 0.1789(5) 0.9359(3) 0.30282(16) 0.0297 1.0000 Uani . U . . . . . C3 C 0.2201(5) 0.8426(3) 0.38841(17) 0.0354 1.0000 Uani . U . . . . . C4 C 0.4275(5) 0.6848(4) 0.37895(19) 0.0407 1.0000 Uani . U . . . . . C5 C 0.4399(5) 0.5387(3) 0.31247(18) 0.0366 1.0000 Uani . U . . . . . C6 C 0.4041(4) 0.6350(3) 0.22668(16) 0.0312 1.0000 Uani . U . . . . . C7 C 0.2025(4) 0.8962(3) 0.14502(15) 0.0269 1.0000 Uani . U . . . . . C8 C 0.0041(4) 0.7139(3) 0.25599(15) 0.0258 1.0000 Uani . U . . . . . C9 C 0.0118(4) 0.5461(3) 0.20342(15) 0.0255 1.0000 Uani . U . . . . . O1 O 0.0457(4) 0.3831(2) 0.23845(11) 0.0411 1.0000 Uani . U . . . . . O2 O -0.0176(3) 0.5762(2) 0.12743(11) 0.0380 1.0000 Uani . U . . . . . N1 N 0.0344(4) 1.0807(2) 0.14159(13) 0.0304 1.0000 Uani . U . . . . . O11 O -0.0894(3) 0.3620(2) 0.41219(11) 0.0362 1.0000 Uani . . . . . . . O12 O 0.6452(3) 0.1099(2) 0.40720(11) 0.0414 1.0000 Uani . . . . . . . O13 O 0.6208(3) 0.0994(3) 0.22488(13) 0.0492 1.0000 Uani . . . . . . . O14 O 0.4803(3) 0.2224(2) 0.07204(12) 0.0455 1.0000 Uani . . . . . . . O15 O 0.2423(3) 0.2704(2) 0.50125(12) 0.0382 1.0000 Uani . . . . . . . O16 O 0.2411(3) 0.5720(3) -0.03548(12) 0.0516 1.0000 Uani . . . . . . . O17 O -0.2144(4) 0.8767(2) 0.03210(11) 0.0479 1.0000 Uani . . . . . . . H21 H 0.2772 1.0061 0.2841 0.0367 1.0000 Uiso R . . . . . . H22 H 0.0366 1.0237 0.3120 0.0363 1.0000 Uiso R . . . . . . H32 H 0.2231 0.9382 0.4269 0.0442 1.0000 Uiso R . . . . . . H31 H 0.1031 0.7930 0.4145 0.0446 1.0000 Uiso R . . . . . . H41 H 0.5435 0.7356 0.3629 0.0501 1.0000 Uiso R . . . . . . H42 H 0.4392 0.6177 0.4322 0.0513 1.0000 Uiso R . . . . . . H51 H 0.5818 0.4478 0.3048 0.0439 1.0000 Uiso R . . . . . . H52 H 0.3342 0.4694 0.3333 0.0420 1.0000 Uiso R . . . . . . H61 H 0.5192 0.6919 0.2048 0.0362 1.0000 Uiso R . . . . . . H62 H 0.4045 0.5392 0.1856 0.0368 1.0000 Uiso R . . . . . . H71 H 0.3335 0.9243 0.1294 0.0334 1.0000 Uiso R . . . . . . H72 H 0.1903 0.8133 0.1029 0.0329 1.0000 Uiso R . . . . . . H82 H -0.0083 0.6739 0.3170 0.0302 1.0000 Uiso R . . . . . . H81 H -0.1240 0.8160 0.2501 0.0312 1.0000 Uiso R . . . . . . H11 H 0.0565 1.1708 0.1719 0.0468 1.0000 Uiso R . . . . . . H12 H 0.0341 1.1223 0.0882 0.0478 1.0000 Uiso R . . . . . . H13 H -0.0938 1.0678 0.1636 0.0467 1.0000 Uiso R . . . . . . H111 H -0.1532 0.2848 0.4170 0.0552 1.0000 Uiso R . . . . . . H112 H -0.0435 0.3707 0.3606 0.0547 1.0000 Uiso R . . . . . . H121 H 0.5284 0.1618 0.4335 0.0603 1.0000 Uiso R . . . . . . H122 H 0.6736 0.0007 0.4280 0.0599 1.0000 Uiso R . . . . . . H131 H 0.5922 0.1293 0.2756 0.0716 1.0000 Uiso R . . . . . . H132 H 0.5287 0.1668 0.1995 0.0711 1.0000 Uiso R . . . . . . H141 H 0.5381 0.3066 0.0567 0.0688 1.0000 Uiso R . . . . . . H142 H 0.3978 0.2197 0.0418 0.0694 1.0000 Uiso R . . . . . . H151 H 0.2205 0.3691 0.5278 0.0576 1.0000 Uiso R . . . . . . H152 H 0.1468 0.2910 0.4721 0.0573 1.0000 Uiso R . . . . . . H161 H 0.1896 0.5604 0.0157 0.0824 1.0000 Uiso R . . . . . . H162 H 0.1911 0.5207 -0.0678 0.0823 1.0000 Uiso R . . . . . . H171 H -0.1693 0.7953 0.0689 0.0660 1.0000 Uiso R . . . . . . H172 H -0.3193 0.9696 0.0458 0.0663 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 C1 0.0270(14) 0.0197(9) 0.0254(12) 0.0009(8) -0.0022(11) -0.0080(9) C2 0.0352(17) 0.0217(10) 0.0327(12) -0.0021(8) -0.0017(11) -0.0114(11) C3 0.0467(17) 0.0323(11) 0.0312(13) -0.0045(10) -0.0070(13) -0.0165(11) C4 0.0461(18) 0.0414(13) 0.0394(16) 0.0068(11) -0.0171(15) -0.0155(12) C5 0.0332(17) 0.0296(11) 0.0437(15) 0.0044(9) -0.0131(13) -0.0012(12) C6 0.0304(15) 0.0270(10) 0.0326(13) -0.0042(9) -0.0016(12) -0.0046(11) C7 0.0313(16) 0.0240(10) 0.0262(13) 0.0007(9) -0.0014(12) -0.0122(10) C8 0.0286(15) 0.0227(9) 0.0252(14) 0.0009(9) -0.0009(12) -0.0086(10) C9 0.0299(16) 0.0264(9) 0.0215(12) 0.0026(8) -0.0046(11) -0.0108(11) O1 0.0721(16) 0.0235(7) 0.0309(11) 0.0038(7) -0.0108(11) -0.0190(9) O2 0.0575(14) 0.0386(9) 0.0255(10) 0.0027(7) -0.0147(10) -0.0214(10) N1 0.0434(15) 0.0241(9) 0.0261(12) 0.0046(8) -0.0099(11) -0.0122(9) O11 0.0473(13) 0.0345(8) 0.0292(11) -0.0010(7) -0.0067(10) -0.0157(9) O12 0.0425(13) 0.0410(9) 0.0365(12) 0.0020(8) -0.0008(10) -0.0102(10) O13 0.0458(14) 0.0494(10) 0.0464(13) 0.0019(9) -0.0067(12) -0.0064(11) O14 0.0476(14) 0.0407(9) 0.0496(13) 0.0036(9) -0.0112(11) -0.0145(10) O15 0.0384(12) 0.0374(9) 0.0382(12) -0.0040(8) -0.0099(10) -0.0075(9) O16 0.0616(16) 0.0657(12) 0.0380(13) -0.0116(10) -0.0029(12) -0.0358(13) O17 0.0615(15) 0.0398(9) 0.0311(12) 0.0057(8) -0.0064(12) -0.0001(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 4.99(18) 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 C1 . C2 . 1.529(4) yes C1 . C6 . 1.540(4) yes C1 . C7 . 1.533(3) yes C1 . C8 . 1.552(4) yes C2 . C3 . 1.515(4) yes C2 . H21 . 0.951 no C2 . H22 . 0.978 no C3 . C4 . 1.521(4) yes C3 . H32 . 0.965 no C3 . H31 . 0.979 no C4 . C5 . 1.522(4) yes C4 . H41 . 0.953 no C4 . H42 . 0.953 no C5 . C6 . 1.518(4) yes C5 . H51 . 0.985 no C5 . H52 . 0.992 no C6 . H61 . 0.987 no C6 . H62 . 0.985 no C7 . N1 . 1.492(3) yes C7 . H71 . 0.955 no C7 . H72 . 0.961 no C8 . C9 . 1.510(3) yes C8 . H82 . 0.987 no C8 . H81 . 0.979 no C9 . O1 . 1.258(3) yes C9 . O2 . 1.253(3) yes N1 . H11 . 0.903 no N1 . H12 . 0.880 no N1 . H13 . 0.904 no O11 . H111 . 0.800 no O11 . H112 . 0.823 no O12 . H121 . 0.813 no O12 . H122 . 0.826 no O13 . H131 . 0.818 no O13 . H132 . 0.826 no O14 . H141 . 0.825 no O14 . H142 . 0.809 no O15 . H151 . 0.819 no O15 . H152 . 0.839 no O16 . H161 . 0.828 no O16 . H162 . 0.827 no O17 . H171 . 0.839 no O17 . H172 . 0.829 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 . C1 . C6 . 109.4(3) yes C2 . C1 . C7 . 109.73(17) yes C6 . C1 . C7 . 105.77(16) yes C2 . C1 . C8 . 108.30(16) yes C6 . C1 . C8 . 111.67(17) yes C7 . C1 . C8 . 112.0(2) yes C1 . C2 . C3 . 114.18(18) yes C1 . C2 . H21 . 109.4 no C3 . C2 . H21 . 107.9 no C1 . C2 . H22 . 107.8 no C3 . C2 . H22 . 107.9 no H21 . C2 . H22 . 109.6 no C2 . C3 . C4 . 111.94(19) yes C2 . C3 . H32 . 109.3 no C4 . C3 . H32 . 108.7 no C2 . C3 . H31 . 109.0 no C4 . C3 . H31 . 111.0 no H32 . C3 . H31 . 106.8 no C3 . C4 . C5 . 111.1(3) yes C3 . C4 . H41 . 111.4 no C5 . C4 . H41 . 109.1 no C3 . C4 . H42 . 109.6 no C5 . C4 . H42 . 106.9 no H41 . C4 . H42 . 108.5 no C4 . C5 . C6 . 110.9(2) yes C4 . C5 . H51 . 107.6 no C6 . C5 . H51 . 108.7 no C4 . C5 . H52 . 109.8 no C6 . C5 . H52 . 110.0 no H51 . C5 . H52 . 109.7 no C1 . C6 . C5 . 113.24(17) yes C1 . C6 . H61 . 108.2 no C5 . C6 . H61 . 108.2 no C1 . C6 . H62 . 107.9 no C5 . C6 . H62 . 109.6 no H61 . C6 . H62 . 109.6 no C1 . C7 . N1 . 114.98(16) yes C1 . C7 . H71 . 108.8 no N1 . C7 . H71 . 106.9 no C1 . C7 . H72 . 109.2 no N1 . C7 . H72 . 107.2 no H71 . C7 . H72 . 109.6 no C1 . C8 . C9 . 116.12(16) yes C1 . C8 . H82 . 108.0 no C9 . C8 . H82 . 108.0 no C1 . C8 . H81 . 109.1 no C9 . C8 . H81 . 107.7 no H82 . C8 . H81 . 107.5 no C8 . C9 . O1 . 118.3(3) yes C8 . C9 . O2 . 118.44(19) yes O1 . C9 . O2 . 123.3(2) yes C7 . N1 . H11 . 110.0 no C7 . N1 . H12 . 110.7 no H11 . N1 . H12 . 107.8 no C7 . N1 . H13 . 111.4 no H11 . N1 . H13 . 108.5 no H12 . N1 . H13 . 108.2 no H111 . O11 . H112 . 106.9 no H121 . O12 . H122 . 103.5 no H131 . O13 . H132 . 109.4 no H141 . O14 . H142 . 111.9 no H151 . O15 . H152 . 106.2 no H161 . O16 . H162 . 111.5 no H171 . O17 . H172 . 121.0 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 C7 . H72 . O2 . 127 0.96 2.51 3.180(4) yes C8 . H81 . O13 1_465 167 0.98 2.34 3.304(4) yes N1 . H11 . O1 1_565 169 0.90 1.91 2.800(4) yes N1 . H12 . O17 2_575 145 0.88 2.06 2.826(4) yes N1 . H13 . O13 1_465 166 0.90 1.95 2.832(4) yes O11 . H111 . O12 1_455 168 0.80 2.16 2.951(4) yes O11 . H112 . O1 . 175 0.82 1.92 2.739(4) yes O12 . H121 . O15 . 176 0.81 1.99 2.799(4) yes O12 . H122 . O15 2_656 172 0.83 2.19 3.011(4) yes O13 . H131 . O12 . 155 0.82 2.17 2.932(4) yes O13 . H132 . O14 . 138 0.83 2.10 2.771(4) yes O14 . H141 . O16 2_665 158 0.82 1.93 2.708(4) yes O14 . H142 . O17 2_565 163 0.81 2.15 2.930(4) yes O15 . H151 . O11 2_566 166 0.82 2.11 2.909(4) yes O15 . H152 . O11 . 174 0.84 1.94 2.778(4) yes O16 . H161 . O2 . 162 0.83 2.02 2.826(4) yes O16 . H162 . O2 2_565 168 0.83 1.95 2.763(4) yes O17 . H171 . O2 . 165 0.84 1.92 2.739(4) yes O17 . H172 . O14 1_465 167 0.83 1.96 2.771(4) yes