#------------------------------------------------------------------------------ #$Date: 2012-02-24 19:13:23 +0200 (Fri, 24 Feb 2012) $ #$Revision: 34330 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/10/22/4102233.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4102233 loop_ _publ_author_name 'Mujeeb Khan' 'Volker Enkelmann' 'Gunther Brunklaus' _publ_contact_author_address ; Max-Planck-Institute for Polymer Research Ackermannweg 10 D-55128 Mainz Germany ; _publ_contact_author_email brunklaus@mpip-mainz.mpg.de _publ_contact_author_fax '+49 379100' _publ_contact_author_name 'Gunther Brunklaus' _publ_contact_author_phone '+49 379240' _publ_section_title ; Crystal Engineering of Pharmaceutical Co-crystals: Application of Methyl Paraben as Molecular Hook ; _journal_name_full 'Journal of the American Chemical Society' _journal_page_first 5254 _journal_page_last 5263 _journal_volume 132 _journal_year 2010 _chemical_absolute_configuration ad _chemical_formula_moiety 'C28 H32 N2 O5' _chemical_formula_sum 'C28 H32 N2 O5' _chemical_formula_weight 476.57 _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 09-05-26 _audit_creation_method CRYSTALS_ver_12.84 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.9621(2) _cell_length_b 11.4794(3) _cell_length_c 21.7107(6) _cell_measurement_reflns_used 0 _cell_measurement_temperature 120 _cell_measurement_theta_max 0 _cell_measurement_theta_min 0 _cell_volume 2482.81(11) _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _diffrn_ambient_temperature 120 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.069 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 22363 _diffrn_reflns_theta_full 29.537 _diffrn_reflns_theta_max 29.537 _diffrn_reflns_theta_min 1.876 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.65 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.275 _exptl_crystal_description prism _exptl_crystal_F_000 1016 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.32 _refine_diff_density_min -0.30 _refine_ls_abs_structure_details 'Flack (1983), 3003 Friedel-pairs' _refine_ls_abs_structure_Flack 0.1(09) _refine_ls_goodness_of_fit_ref 1.1090 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 317 _refine_ls_number_reflns 4239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0374 _refine_ls_shift/su_max 0.000176 _refine_ls_structure_factor_coef F _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: 1.23 0.547 0.917 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0567 _refine_ls_wR_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.0416 _reflns_limit_h_max 13 _reflns_limit_h_min -13 _reflns_limit_k_max 15 _reflns_limit_k_min 0 _reflns_limit_l_max 30 _reflns_limit_l_min 0 _reflns_number_gt 4239 _reflns_number_total 6881 _reflns_threshold_expression I>3.0\s(I) _[local]_cod_data_source_file ja100146f_si_002.cif _[local]_cod_data_source_block CRYSTALS_cif _[local]_cod_cif_authors_sg_H-M 'P 21 21 21 ' _cod_database_code 4102233 loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 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 C1 C 0.5446(2) 0.88445(17) 0.22826(9) 0.0312 1.0000 Uani . C2 C 0.56412(19) 0.78115(17) 0.19483(8) 0.0272 1.0000 Uani . C3 C 0.45535(18) 0.71664(16) 0.17612(7) 0.0229 1.0000 Uani . C4 C 0.32469(17) 0.75890(15) 0.19073(7) 0.0214 1.0000 Uani . C5 C 0.31552(18) 0.86427(17) 0.22436(7) 0.0253 1.0000 Uani . C6 C 0.18712(19) 0.91035(17) 0.23843(8) 0.0282 1.0000 Uani . C7 C 0.0730(2) 0.85453(18) 0.22069(8) 0.0294 1.0000 Uani . C8 C 0.08163(19) 0.74721(16) 0.18891(8) 0.0251 1.0000 Uani . C9 C 0.20389(18) 0.69987(16) 0.17424(7) 0.0227 1.0000 Uani . C10 C -0.0375(2) 0.59145(19) 0.14134(9) 0.0332 1.0000 Uani . C11 C 0.47285(17) 0.60369(16) 0.14076(8) 0.0218 1.0000 Uani . C12 C 0.44047(18) 0.62229(14) 0.07227(7) 0.0225 1.0000 Uani . C13 C 0.5456(2) 0.69427(16) 0.03695(8) 0.0266 1.0000 Uani . C14 C 0.5526(2) 0.64735(18) -0.02938(8) 0.0302 1.0000 Uani . C15 C 0.4085(2) 0.6355(2) -0.05460(8) 0.0360 1.0000 Uani . C16 C 0.3359(2) 0.54069(19) -0.01710(8) 0.0323 1.0000 Uani . C17 C 0.5394(2) 0.45256(18) 0.02013(9) 0.0329 1.0000 Uani . C18 C 0.61605(19) 0.52554(19) -0.02890(9) 0.0323 1.0000 Uani . C19 C 0.7641(2) 0.5272(2) -0.01581(10) 0.0395 1.0000 Uani . C20 C 0.8576(3) 0.5035(2) -0.05566(13) 0.0542 1.0000 Uani . C21 C -0.1769(2) 0.15669(19) 0.15308(8) 0.0326 1.0000 Uani . C22 C -0.0441(2) 0.20869(17) 0.13870(8) 0.0286 1.0000 Uani . C23 C 0.0644(2) 0.17161(17) 0.17405(8) 0.0310 1.0000 Uani . C24 C 0.1904(2) 0.21754(17) 0.16546(9) 0.0318 1.0000 Uani . C25 C 0.2107(2) 0.30183(16) 0.11974(9) 0.0311 1.0000 Uani . C26 C 0.1036(2) 0.33705(18) 0.08315(10) 0.0351 1.0000 Uani . C27 C -0.0232(2) 0.29131(18) 0.09294(9) 0.0326 1.0000 Uani . C28 C -0.4105(2) 0.1676(2) 0.13852(13) 0.0525 1.0000 Uani . O1 O -0.04017(13) 0.69810(13) 0.17500(6) 0.0306 1.0000 Uani . O2 O 0.60493(12) 0.55804(11) 0.14767(6) 0.0262 1.0000 Uani . O21 O -0.19430(16) 0.07452(14) 0.18679(7) 0.0423 1.0000 Uani . O22 O -0.27727(15) 0.21195(14) 0.12440(8) 0.0423 1.0000 Uani . O23 O 0.33632(15) 0.34420(13) 0.11391(7) 0.0407 1.0000 Uani . N1 N 0.42579(16) 0.92592(14) 0.24342(7) 0.0298 1.0000 Uani . N2 N 0.41241(15) 0.51100(13) 0.03933(7) 0.0267 1.0000 Uani . H11 H 0.6217 0.9270 0.2408 0.0384 1.0000 Uiso R H21 H 0.6522 0.7559 0.1847 0.0358 1.0000 Uiso R H61 H 0.1811 0.9819 0.2603 0.0338 1.0000 Uiso R H71 H -0.0124 0.8871 0.2297 0.0390 1.0000 Uiso R H91 H 0.2084 0.6279 0.1527 0.0294 1.0000 Uiso R H101 H -0.1267 0.5656 0.1342 0.0410 1.0000 Uiso R H102 H 0.0065 0.6031 0.1030 0.0410 1.0000 Uiso R H103 H 0.0097 0.5344 0.1645 0.0410 1.0000 Uiso R H111 H 0.4109 0.5487 0.1569 0.0271 1.0000 Uiso R H121 H 0.3597 0.6662 0.0709 0.0293 1.0000 Uiso R H131 H 0.5212 0.7743 0.0368 0.0354 1.0000 Uiso R H132 H 0.6305 0.6854 0.0563 0.0354 1.0000 Uiso R H141 H 0.6037 0.6984 -0.0546 0.0406 1.0000 Uiso R H151 H 0.3624 0.7073 -0.0495 0.0462 1.0000 Uiso R H152 H 0.4101 0.6152 -0.0970 0.0462 1.0000 Uiso R H161 H 0.2488 0.5667 -0.0058 0.0418 1.0000 Uiso R H162 H 0.3284 0.4729 -0.0419 0.0418 1.0000 Uiso R H171 H 0.5954 0.4429 0.0552 0.0464 1.0000 Uiso R H172 H 0.5178 0.3784 0.0035 0.0464 1.0000 Uiso R H181 H 0.6030 0.4909 -0.0682 0.0397 1.0000 Uiso R H191 H 0.7913 0.5456 0.0250 0.0496 1.0000 Uiso R H201 H 0.9497 0.5054 -0.0443 0.0700 1.0000 Uiso R H202 H 0.8327 0.4850 -0.0967 0.0700 1.0000 Uiso R H231 H 0.0506 0.1139 0.2047 0.0400 1.0000 Uiso R H241 H 0.2635 0.1924 0.1902 0.0407 1.0000 Uiso R H261 H 0.1182 0.3923 0.0513 0.0470 1.0000 Uiso R H271 H -0.0968 0.3174 0.0688 0.0454 1.0000 Uiso R H281 H -0.4760 0.2110 0.1165 0.0684 1.0000 Uiso R H282 H -0.4263 0.1750 0.1815 0.0684 1.0000 Uiso R H283 H -0.4160 0.0878 0.1271 0.0684 1.0000 Uiso R H2 H 0.3399 0.4148 0.0834 0.0500 1.0000 Uiso R H1 H 0.6182 0.5228 0.1840 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 C1 0.0268(10) 0.0377(11) 0.0291(9) -0.0072(8) -0.0011(7) -0.0081(9) C2 0.0207(9) 0.0370(10) 0.0240(8) -0.0006(7) 0.0011(6) -0.0018(8) C3 0.0241(8) 0.0292(9) 0.0153(7) 0.0028(6) -0.0010(6) -0.0018(7) C4 0.0233(9) 0.0262(9) 0.0149(7) 0.0018(6) 0.0008(6) 0.0001(7) C5 0.0264(9) 0.0321(10) 0.0175(7) -0.0007(7) 0.0011(7) -0.0028(8) C6 0.0291(10) 0.0328(10) 0.0228(8) -0.0044(7) 0.0016(7) 0.0022(8) C7 0.0269(9) 0.0377(10) 0.0236(8) -0.0024(8) 0.0014(7) 0.0052(8) C8 0.0239(9) 0.0333(9) 0.0183(7) 0.0034(7) -0.0015(6) -0.0027(7) C9 0.0259(9) 0.0260(9) 0.0162(7) 0.0024(6) 0.0004(6) -0.0027(7) C10 0.0287(10) 0.0442(11) 0.0268(9) -0.0003(8) -0.0005(8) -0.0102(9) C11 0.0194(8) 0.0265(8) 0.0196(7) 0.0033(6) 0.0013(6) 0.0002(7) C12 0.0235(9) 0.0234(8) 0.0205(7) -0.0007(6) 0.0010(6) 0.0003(7) C13 0.0302(9) 0.0257(9) 0.0240(8) 0.0029(7) 0.0038(7) 0.0002(8) C14 0.0298(10) 0.0413(11) 0.0195(8) 0.0052(8) 0.0039(7) -0.0010(9) C15 0.0368(11) 0.0496(12) 0.0216(8) 0.0059(8) -0.0024(8) 0.0023(10) C16 0.0304(10) 0.0429(12) 0.0236(9) -0.0053(8) -0.0031(7) -0.0029(9) C17 0.0371(11) 0.0308(10) 0.0309(9) -0.0091(8) 0.0006(8) 0.0048(8) C18 0.0293(10) 0.0434(11) 0.0241(9) -0.0098(8) 0.0002(7) 0.0005(9) C19 0.0333(11) 0.0474(13) 0.0378(11) -0.0123(10) -0.0001(8) 0.0024(10) C20 0.0358(13) 0.0632(17) 0.0635(16) -0.0216(13) 0.0038(11) -0.0014(12) C21 0.0328(11) 0.0372(11) 0.0277(9) -0.0094(8) 0.0011(8) -0.0011(9) C22 0.0315(9) 0.0258(9) 0.0285(9) -0.0092(7) 0.0008(8) -0.0008(8) C23 0.0359(11) 0.0290(10) 0.0282(9) -0.0015(7) 0.0030(8) -0.0008(8) C24 0.0330(10) 0.0309(10) 0.0315(9) -0.0012(8) -0.0031(8) -0.0001(8) C25 0.0337(10) 0.0244(9) 0.0352(9) -0.0039(8) 0.0008(8) -0.0044(8) C26 0.0422(12) 0.0261(9) 0.0370(10) 0.0026(8) -0.0046(9) -0.0024(9) C27 0.0355(11) 0.0285(10) 0.0337(10) -0.0039(8) -0.0062(8) -0.0001(8) C28 0.0305(12) 0.0645(16) 0.0626(15) -0.0035(13) -0.0023(11) -0.0052(11) O1 0.0210(6) 0.0433(8) 0.0273(6) -0.0041(6) -0.0005(5) -0.0036(6) O2 0.0225(6) 0.0311(7) 0.0249(6) 0.0041(5) -0.0031(5) 0.0044(5) O21 0.0378(9) 0.0457(9) 0.0434(8) 0.0028(7) 0.0038(7) -0.0072(7) O22 0.0292(8) 0.0448(9) 0.0529(9) -0.0022(7) -0.0036(7) -0.0014(7) O23 0.0333(8) 0.0379(8) 0.0511(9) 0.0112(7) -0.0047(6) -0.0094(7) N1 0.0299(9) 0.0320(8) 0.0274(7) -0.0072(6) 0.0002(6) -0.0040(7) N2 0.0280(8) 0.0293(8) 0.0226(7) -0.0022(6) 0.0005(6) -0.0028(7) 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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 C1 N1 123.99(17) yes C2 C1 H11 118.1 no N1 C1 H11 118.0 no C1 C2 C3 119.92(17) yes C1 C2 H21 120.4 no C3 C2 H21 119.7 no C2 C3 C4 118.11(16) yes C2 C3 C11 121.32(16) yes C4 C3 C11 120.57(16) yes C3 C4 C5 117.69(16) yes C3 C4 C9 123.57(16) yes C5 C4 C9 118.73(16) yes C4 C5 C6 119.22(16) yes C4 C5 N1 123.03(16) yes C6 C5 N1 117.74(17) yes C5 C6 C7 121.15(17) yes C5 C6 H61 119.2 no C7 C6 H61 119.7 no C6 C7 C8 119.84(17) yes C6 C7 H71 120.3 no C8 C7 H71 119.8 no C7 C8 C9 120.82(17) yes C7 C8 O1 114.31(16) yes C9 C8 O1 124.87(16) yes C4 C9 C8 120.18(16) yes C4 C9 H91 119.8 no C8 C9 H91 120.0 no O1 C10 H101 109.5 no O1 C10 H102 109.7 no H101 C10 H102 109.5 no O1 C10 H103 109.3 no H101 C10 H103 109.5 no H102 C10 H103 109.5 no C3 C11 C12 110.30(14) yes C3 C11 O2 111.55(15) yes C12 C11 O2 110.30(14) yes C3 C11 H111 107.9 no C12 C11 H111 108.2 no O2 C11 H111 108.5 no C11 C12 C13 114.46(14) yes C11 C12 N2 112.61(14) yes C13 C12 N2 110.42(13) yes C11 C12 H121 106.4 no C13 C12 H121 106.0 no N2 C12 H121 106.3 no C12 C13 C14 108.01(15) yes C12 C13 H131 110.3 no C14 C13 H131 110.3 no C12 C13 H132 109.2 no C14 C13 H132 109.6 no H131 C13 H132 109.5 no C13 C14 C15 108.72(16) yes C13 C14 C18 109.34(15) yes C15 C14 C18 107.76(17) yes C13 C14 H141 110.4 no C15 C14 H141 110.4 no C18 C14 H141 110.2 no C14 C15 C16 108.19(15) yes C14 C15 H151 109.4 no C16 C15 H151 108.9 no C14 C15 H152 110.5 no C16 C15 H152 110.3 no H151 C15 H152 109.5 no C15 C16 N2 110.97(16) yes C15 C16 H161 110.1 no N2 C16 H161 109.1 no C15 C16 H162 108.4 no N2 C16 H162 108.7 no H161 C16 H162 109.5 no C18 C17 N2 111.45(16) yes C18 C17 H171 108.8 no N2 C17 H171 109.1 no C18 C17 H172 109.4 no N2 C17 H172 108.6 no H171 C17 H172 109.5 no C14 C18 C17 107.05(15) yes C14 C18 C19 113.21(17) yes C17 C18 C19 111.08(17) yes C14 C18 H181 108.6 no C17 C18 H181 108.8 no C19 C18 H181 108.0 no C18 C19 C20 125.1(2) yes C18 C19 H191 117.3 no C20 C19 H191 117.5 no C19 C20 H201 121.0 no C19 C20 H202 119.0 no H201 C20 H202 120.0 no C22 C21 O21 124.75(19) yes C22 C21 O22 112.17(17) yes O21 C21 O22 123.08(19) yes C21 C22 C23 116.94(17) yes C21 C22 C27 123.98(18) yes C23 C22 C27 119.08(18) yes C22 C23 C24 121.14(18) yes C22 C23 H231 119.2 no C24 C23 H231 119.6 no C23 C24 C25 119.54(18) yes C23 C24 H241 120.5 no C25 C24 H241 120.0 no C24 C25 C26 119.65(18) yes C24 C25 O23 116.72(18) yes C26 C25 O23 123.63(18) yes C25 C26 C27 120.15(19) yes C25 C26 H261 119.5 no C27 C26 H261 120.4 no C22 C27 C26 120.40(19) yes C22 C27 H271 119.6 no C26 C27 H271 120.0 no O22 C28 H281 109.7 no O22 C28 H282 109.1 no H281 C28 H282 109.5 no O22 C28 H283 109.6 no H281 C28 H283 109.5 no H282 C28 H283 109.5 no C10 O1 C8 116.67(15) yes C11 O2 H1 113.3 no C28 O22 C21 114.70(18) yes C25 O23 H2 111.7 no C5 N1 C1 117.25(16) yes C17 N2 C12 111.14(14) yes C17 N2 C16 107.97(15) yes C12 N2 C16 107.21(14) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.404(3) yes C1 N1 1.317(3) yes C1 H11 0.950 no C2 C3 1.374(3) yes C2 H21 0.950 no C3 C4 1.425(2) yes C3 C11 1.517(3) yes C4 C5 1.416(2) yes C4 C9 1.427(2) yes C5 C6 1.417(3) yes C5 N1 1.371(2) yes C6 C7 1.360(3) yes C6 H61 0.950 no C7 C8 1.415(3) yes C7 H71 0.950 no C8 C9 1.371(3) yes C8 O1 1.372(2) yes C9 H91 0.950 no C10 O1 1.426(3) yes C10 H101 0.950 no C10 H102 0.950 no C10 H103 0.950 no C11 C12 1.537(2) yes C11 O2 1.424(2) yes C11 H111 0.950 no C12 C13 1.539(2) yes C12 N2 1.490(2) yes C12 H121 0.950 no C13 C14 1.539(2) yes C13 H131 0.950 no C13 H132 0.950 no C14 C15 1.542(3) yes C14 C18 1.534(3) yes C14 H141 0.950 no C15 C16 1.540(3) yes C15 H151 0.950 no C15 H152 0.950 no C16 N2 1.483(2) yes C16 H161 0.950 no C16 H162 0.950 no C17 C18 1.555(3) yes C17 N2 1.491(2) yes C17 H171 0.950 no C17 H172 0.950 no C18 C19 1.502(3) yes C18 H181 0.950 no C19 C20 1.301(3) yes C19 H191 0.950 no C20 H201 0.950 no C20 H202 0.950 no C21 C22 1.484(3) yes C21 O21 1.206(3) yes C21 O22 1.338(3) yes C22 C23 1.393(3) yes C22 C27 1.389(3) yes C23 C24 1.375(3) yes C23 H231 0.950 no C24 C25 1.401(3) yes C24 H241 0.950 no C25 C26 1.391(3) yes C25 O23 1.348(2) yes C26 C27 1.384(3) yes C26 H261 0.950 no C27 H271 0.950 no C28 O22 1.454(3) yes C28 H281 0.950 no C28 H282 0.950 no C28 H283 0.950 no O2 H1 0.896 no O23 H2 1.046 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_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 O23 H2 N2 . 156 1.05 1.63 2.620(2) yes O2 H1 N1 3_645 157 0.90 1.98 2.826(2) yes