#------------------------------------------------------------------------------ #$Date: 2016-03-24 14:12:59 +0200 (Thu, 24 Mar 2016) $ #$Revision: 179656 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/51/09/4510908.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_4510908 loop_ _publ_author_name 'Mukherjee, Arijit' 'Grobelny, Pawel' 'Thakur, Tejender S.' 'Desiraju, Gautam R.' _publ_section_title ; Polymorphs, Pseudopolymorphs, and Co-Crystals of Orcinol: Exploring the Structural Landscape with High Throughput Crystallography ; _journal_issue 6 _journal_name_full 'Crystal Growth & Design' _journal_page_first 2637 _journal_paper_doi 10.1021/cg200361x _journal_volume 11 _journal_year 2011 _chemical_compound_source 'see text' _chemical_formula_moiety '2(C7 H10 N2), C7 H8 O2' _chemical_formula_sum 'C21 H28 N4 O2' _chemical_formula_weight 368.47 _chemical_name_common 'Orcinol: N,N-dimethyl,4-aminopyridine' _chemical_name_systematic ? _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 83.929(6) _cell_angle_beta 81.521(6) _cell_angle_gamma 86.524(6) _cell_formula_units_Z 2 _cell_length_a 7.8586(19) _cell_length_b 8.1455(19) _cell_length_c 16.239(4) _cell_measurement_reflns_used 7658 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.7 _cell_measurement_theta_min 3.1 _cell_volume 1021.3(4) _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_detector CCD _diffrn_detector_area_resol_mean 13.6612 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4000 2theta: 29.6000 ; _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support Fiber _diffrn_orient_matrix_type FS_PROCESS _diffrn_orient_matrix_UB_11 -0.005598 _diffrn_orient_matrix_UB_12 0.114380 _diffrn_orient_matrix_UB_13 0.017657 _diffrn_orient_matrix_UB_21 0.091583 _diffrn_orient_matrix_UB_22 -0.033369 _diffrn_orient_matrix_UB_23 0.035983 _diffrn_orient_matrix_UB_31 0.090378 _diffrn_orient_matrix_UB_32 0.032833 _diffrn_orient_matrix_UB_33 -0.048035 _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0627 _diffrn_reflns_av_sigmaI/netI 0.0834 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 10823 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 3.08 _diffrn_source 'Sealed Tube' _diffrn_source_current 12.0 _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description Block _exptl_crystal_F_000 396 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.920 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.121 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 249 _refine_ls_number_reflns 4662 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.1706 _refine_ls_R_factor_gt 0.1087 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1805P)^2^+0.5977P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2962 _refine_ls_wR_factor_ref 0.3372 _reflns_number_gt 2565 _reflns_number_total 4662 _reflns_threshold_expression I>2\s(I) _cod_data_source_file 818153.cif _cod_data_source_block datam _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius ; _cod_database_code 4510908 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z 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 N1 0.055(2) 0.042(2) 0.054(2) 0.0001(18) -0.0031(18) -0.0074(17) N2 0.063(3) 0.044(2) 0.042(2) 0.0027(16) -0.0069(17) -0.0059(17) C8 0.066(3) 0.037(2) 0.049(3) -0.010(2) 0.001(2) -0.008(2) C9 0.062(3) 0.046(2) 0.039(2) -0.009(2) -0.003(2) -0.011(2) C10 0.039(2) 0.039(2) 0.034(2) -0.0026(17) 0.0013(16) -0.0091(17) C11 0.060(3) 0.043(2) 0.036(2) -0.0078(19) 0.0016(19) -0.007(2) C12 0.072(3) 0.048(3) 0.035(2) 0.000(2) -0.003(2) -0.007(2) C13 0.096(4) 0.058(3) 0.044(3) 0.009(2) -0.023(3) -0.019(3) C14 0.077(4) 0.039(2) 0.057(3) 0.000(2) 0.000(2) 0.005(2) N3 0.047(2) 0.0357(18) 0.046(2) -0.0028(16) -0.0101(16) -0.0020(15) N4 0.058(2) 0.0372(18) 0.0320(17) 0.0009(15) -0.0023(15) -0.0010(15) C15 0.048(3) 0.036(2) 0.050(3) -0.0138(19) -0.0163(19) 0.0027(17) C16 0.042(2) 0.041(2) 0.034(2) -0.0080(17) -0.0095(17) 0.0058(17) C17 0.035(2) 0.0329(19) 0.036(2) -0.0024(16) -0.0060(16) 0.0069(15) C18 0.046(2) 0.033(2) 0.031(2) -0.0029(16) -0.0085(16) 0.0025(16) C19 0.050(3) 0.037(2) 0.038(2) -0.0033(17) -0.0089(18) 0.0018(18) C20 0.075(3) 0.048(3) 0.033(2) 0.0049(19) 0.000(2) 0.006(2) C21 0.064(3) 0.039(2) 0.051(3) -0.003(2) -0.005(2) -0.008(2) O1 0.0410(17) 0.0413(16) 0.0569(19) 0.0069(14) -0.0038(13) -0.0112(13) O3 0.0411(17) 0.0386(16) 0.062(2) 0.0048(14) -0.0155(14) -0.0017(12) C1 0.034(2) 0.0316(19) 0.0327(19) -0.0088(15) 0.0006(15) -0.0076(15) C2 0.0269(19) 0.0354(19) 0.035(2) -0.0055(16) -0.0049(15) -0.0026(15) C3 0.037(2) 0.0301(18) 0.0338(19) -0.0084(15) -0.0069(15) 0.0012(15) C4 0.031(2) 0.0339(19) 0.0310(18) -0.0072(15) -0.0004(14) -0.0075(15) C5 0.033(2) 0.0354(19) 0.0265(18) -0.0084(15) -0.0026(14) -0.0045(15) C6 0.036(2) 0.0332(19) 0.0301(19) -0.0061(15) -0.0064(15) 0.0018(15) C7 0.034(2) 0.047(2) 0.044(2) -0.0069(19) -0.0038(17) -0.0033(17) loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N1 N Uani 0.8676(5) 0.7312(4) 0.0811(2) 1.000 0.0509(12) . . N2 N Uani 0.7007(5) 1.1616(4) -0.0548(2) 1.000 0.0501(14) . . C8 C Uani 0.8503(6) 0.7353(5) 0.0003(3) 1.000 0.0509(16) . . C9 C Uani 0.7935(6) 0.8729(5) -0.0474(3) 1.000 0.0487(14) . . C10 C Uani 0.7509(5) 1.0212(5) -0.0111(2) 1.000 0.0378(12) . . C11 C Uani 0.7668(6) 1.0172(5) 0.0741(3) 1.000 0.0467(14) . . C12 C Uani 0.8254(7) 0.8731(6) 0.1158(3) 1.000 0.0523(16) . . C13 C Uani 0.6900(8) 1.1671(6) -0.1436(3) 1.000 0.0651(19) . . C14 C Uani 0.6540(7) 1.3117(5) -0.0150(3) 1.000 0.0593(18) . . N3 N Uani 0.1310(4) 0.2475(4) 0.5754(2) 1.000 0.0426(11) . . N4 N Uani 0.3202(5) 0.6796(4) 0.4384(2) 1.000 0.0432(11) . . C15 C Uani 0.1442(6) 0.2703(5) 0.4919(3) 1.000 0.0432(16) . . C16 C Uani 0.2065(5) 0.4087(5) 0.4438(2) 1.000 0.0386(12) . . C17 C Uani 0.2605(5) 0.5379(5) 0.4831(2) 1.000 0.0350(11) . . C18 C Uani 0.2483(5) 0.5146(5) 0.5705(2) 1.000 0.0366(12) . . C19 C Uani 0.1836(5) 0.3703(5) 0.6120(3) 1.000 0.0416(14) . . C20 C Uani 0.3416(7) 0.6950(6) 0.3472(3) 1.000 0.0538(16) . . C21 C Uani 0.3681(6) 0.8150(5) 0.4795(3) 1.000 0.0515(16) . . O1 O Uani 1.0408(4) 0.5058(3) 0.17206(19) 1.000 0.0472(10) . . O3 O Uani 1.0426(4) 0.0057(3) 0.34325(19) 1.000 0.0471(10) . . C1 C Uani 0.9476(5) 0.3788(4) 0.2132(2) 1.000 0.0327(11) . . C2 C Uani 1.0353(5) 0.2534(4) 0.2578(2) 1.000 0.0322(11) . . C3 C Uani 0.9482(5) 0.1217(4) 0.3012(2) 1.000 0.0332(11) . . C4 C Uani 0.7728(5) 0.1123(4) 0.2998(2) 1.000 0.0318(11) . . C5 C Uani 0.6838(5) 0.2376(4) 0.2553(2) 1.000 0.0313(11) . . C6 C Uani 0.7723(5) 0.3720(5) 0.2119(2) 1.000 0.0329(11) . . C7 C Uani 0.4958(5) 0.2285(5) 0.2539(3) 1.000 0.0416(12) . . H8 H Uiso 0.87910 0.63690 -0.02630 1.000 0.0610 calc R H9 H Uiso 0.78330 0.86690 -0.10460 1.000 0.0590 calc R H11 H Uiso 0.73740 1.11290 0.10280 1.000 0.0560 calc R H12 H Uiso 0.83660 0.87450 0.17320 1.000 0.0630 calc R H13A H Uiso 0.79450 1.11410 -0.17190 1.000 0.0970 calc R H13B H Uiso 0.67910 1.28240 -0.16720 1.000 0.0970 calc R H13C H Uiso 0.58930 1.10850 -0.15160 1.000 0.0970 calc R H14A H Uiso 0.54980 1.29550 0.02570 1.000 0.0890 calc R H14B H Uiso 0.63210 1.40220 -0.05750 1.000 0.0890 calc R H14C H Uiso 0.74830 1.33910 0.01360 1.000 0.0890 calc R H15 H Uiso 0.10780 0.18490 0.46380 1.000 0.0520 calc R H16 H Uiso 0.21310 0.41690 0.38470 1.000 0.0470 calc R H18 H Uiso 0.28410 0.59700 0.60060 1.000 0.0440 calc R H19 H Uiso 0.17600 0.35740 0.67130 1.000 0.0500 calc R H20A H Uiso 0.42710 0.61100 0.32620 1.000 0.0810 calc R H20B H Uiso 0.38090 0.80520 0.32540 1.000 0.0810 calc R H20C H Uiso 0.23120 0.67900 0.32850 1.000 0.0810 calc R H21A H Uiso 0.27390 0.84380 0.52290 1.000 0.0770 calc R H21B H Uiso 0.39110 0.91100 0.43840 1.000 0.0770 calc R H21C H Uiso 0.47190 0.78210 0.50520 1.000 0.0770 calc R H1 H Uiso 0.97570 0.57380 0.14760 1.000 0.0710 calc R H2 H Uiso 1.15550 0.25880 0.25840 1.000 0.0390 calc R H3 H Uiso 0.97850 -0.06890 0.36750 1.000 0.0710 calc R H4 H Uiso 0.71320 0.02080 0.32900 1.000 0.0380 calc R H6 H Uiso 0.71250 0.45770 0.18180 1.000 0.0400 calc R H7A H Uiso 0.44950 0.33570 0.23150 1.000 0.0620 calc R H7B H Uiso 0.43770 0.20040 0.31090 1.000 0.0620 calc R H7C H Uiso 0.47640 0.14330 0.21840 1.000 0.0620 calc R loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 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 C1 O1 H1 109.00 no C3 O3 H3 109.00 no C8 N1 C12 115.5(4) yes C13 N2 C14 117.4(4) yes C10 N2 C13 121.2(3) yes C10 N2 C14 121.4(3) yes C15 N3 C19 115.7(4) yes C17 N4 C20 120.2(3) yes C20 N4 C21 118.4(4) yes C17 N4 C21 121.3(3) yes N1 C8 C9 124.6(4) yes C8 C9 C10 119.8(4) no C9 C10 C11 116.0(4) no N2 C10 C11 121.2(4) yes N2 C10 C9 122.8(3) yes C10 C11 C12 119.5(4) no N1 C12 C11 124.7(4) yes N1 C8 H8 118.00 no C9 C8 H8 118.00 no C8 C9 H9 120.00 no C10 C9 H9 120.00 no C10 C11 H11 120.00 no C12 C11 H11 120.00 no C11 C12 H12 118.00 no N1 C12 H12 118.00 no N2 C13 H13B 109.00 no H13A C13 H13C 109.00 no N2 C13 H13A 109.00 no N2 C13 H13C 109.00 no H13A C13 H13B 109.00 no H13B C13 H13C 110.00 no H14B C14 H14C 109.00 no N2 C14 H14A 109.00 no N2 C14 H14B 109.00 no N2 C14 H14C 109.00 no H14A C14 H14B 109.00 no H14A C14 H14C 110.00 no N3 C15 C16 124.6(4) yes C15 C16 C17 119.2(3) no N4 C17 C18 121.8(4) yes C16 C17 C18 116.5(3) no N4 C17 C16 121.6(3) yes C17 C18 C19 119.0(4) no N3 C19 C18 125.0(4) yes N3 C15 H15 118.00 no C16 C15 H15 118.00 no C15 C16 H16 120.00 no C17 C16 H16 120.00 no C19 C18 H18 121.00 no C17 C18 H18 120.00 no N3 C19 H19 118.00 no C18 C19 H19 118.00 no N4 C20 H20B 110.00 no N4 C20 H20A 110.00 no H20A C20 H20C 109.00 no H20B C20 H20C 109.00 no N4 C20 H20C 110.00 no H20A C20 H20B 109.00 no N4 C21 H21C 109.00 no N4 C21 H21A 109.00 no N4 C21 H21B 110.00 no H21B C21 H21C 109.00 no H21A C21 H21C 109.00 no H21A C21 H21B 109.00 no O1 C1 C6 122.2(3) yes O1 C1 C2 117.5(3) yes C2 C1 C6 120.3(3) no C1 C2 C3 120.3(4) no O3 C3 C2 116.6(3) yes C2 C3 C4 120.0(3) no O3 C3 C4 123.3(3) yes C3 C4 C5 120.0(3) no C4 C5 C6 119.8(4) no C4 C5 C7 120.3(3) no C6 C5 C7 119.9(3) no C1 C6 C5 119.5(3) no C1 C2 H2 120.00 no C3 C2 H2 120.00 no C3 C4 H4 120.00 no C5 C4 H4 120.00 no C1 C6 H6 120.00 no C5 C6 H6 120.00 no C5 C7 H7A 109.00 no C5 C7 H7B 109.00 no C5 C7 H7C 109.00 no H7A C7 H7B 109.00 no H7A C7 H7C 110.00 no H7B C7 H7C 109.00 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.362(4) yes O3 C3 1.356(5) yes O1 H1 0.8400 no O3 H3 0.8400 no N1 C12 1.342(6) yes N1 C8 1.336(6) yes N2 C13 1.453(6) yes N2 C14 1.446(5) yes N2 C10 1.350(5) yes N3 C19 1.332(5) yes N3 C15 1.339(6) yes N4 C17 1.367(5) yes N4 C21 1.444(6) yes N4 C20 1.459(6) yes C8 C9 1.383(6) no C9 C10 1.401(6) no C10 C11 1.404(6) no C11 C12 1.381(7) no C8 H8 0.9500 no C9 H9 0.9500 no C11 H11 0.9500 no C12 H12 0.9500 no C13 H13B 0.9800 no C13 H13A 0.9800 no C13 H13C 0.9800 no C14 H14C 0.9800 no C14 H14B 0.9800 no C14 H14A 0.9800 no C15 C16 1.374(6) no C16 C17 1.404(6) no C17 C18 1.402(5) no C18 C19 1.378(6) no C15 H15 0.9500 no C16 H16 0.9500 no C18 H18 0.9500 no C19 H19 0.9500 no C20 H20C 0.9800 no C20 H20A 0.9800 no C20 H20B 0.9800 no C21 H21B 0.9800 no C21 H21C 0.9800 no C21 H21A 0.9800 no C1 C6 1.385(6) no C1 C2 1.396(5) no C2 C3 1.380(5) no C3 C4 1.389(6) no C4 C5 1.400(5) no C5 C7 1.487(6) no C5 C6 1.401(5) no C2 H2 0.9500 no C4 H4 0.9500 no C6 H6 0.9500 no C7 H7A 0.9800 no C7 H7B 0.9800 no C7 H7C 0.9800 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 N1 2.669(5) . no O3 N3 2.663(4) 2_656 no O3 C20 3.350(6) 1_645 no O1 H8 2.7200 2_765 no O1 H13B 2.8700 2_775 no O3 H15 2.6900 1_655 no N1 O1 2.669(5) . no N3 O3 2.663(4) 2_656 no N1 H6 2.8400 . no N1 H1 1.8400 . no N3 H4 2.8600 2_656 no N3 H3 1.8300 2_656 no C5 C11 3.566(6) 1_545 no C9 C11 3.575(7) 2_775 no C11 C9 3.575(7) 2_775 no C11 C5 3.566(6) 1_565 no C13 C20 3.417(7) 2_675 no C15 C17 3.446(6) 2_566 no C17 C15 3.446(6) 2_566 no C20 C13 3.417(7) 2_675 no C20 O3 3.350(6) 1_465 no C1 H19 3.0200 2_666 no C2 H9 2.9100 2_765 no C4 H12 2.9400 1_545 no C4 H21A 2.9100 2_666 no C4 H18 2.9800 2_666 no C5 H18 2.8700 2_666 no C5 H11 2.7400 1_545 no C6 H11 2.9400 1_545 no C6 H18 3.0500 2_666 no C7 H2 2.6600 1_455 no C7 H11 3.0700 1_545 no C8 H1 2.8800 . no C9 H13A 2.6700 . no C9 H13C 2.9800 . no C9 H14A 3.0600 2_675 no C11 H13C 3.0800 2_675 no C11 H14C 2.7000 . no C11 H14A 2.8700 . no C12 H1 2.6800 . no C13 H20B 3.0700 2_675 no C13 H9 2.5500 . no C14 H11 2.5100 . no C15 H21C 3.0300 2_666 no C15 H3 2.7500 2_656 no C16 H21C 3.0600 2_666 no C16 H20A 2.8400 . no C16 H20C 2.7300 . no C18 H21A 2.7200 . no C18 H21C 2.9000 . no C19 H3 2.8000 2_656 no C20 H13B 2.9400 2_675 no C20 H16 2.5200 . no C21 H18 2.5400 . no H1 C8 2.8800 . no H1 N1 1.8400 . no H1 H6 2.3000 . no H1 C12 2.6800 . no H2 H7B 2.4900 1_655 no H2 C7 2.6600 1_655 no H2 H7A 2.4000 1_655 no H3 N3 1.8300 2_656 no H3 H4 2.3200 . no H3 C15 2.7500 2_656 no H3 C19 2.8000 2_656 no H4 H3 2.3200 . no H4 H7B 2.5700 . no H4 N3 2.8600 2_656 no H6 N1 2.8400 . no H6 H1 2.3000 . no H6 H7A 2.3400 . no H7A H6 2.3400 . no H7A H2 2.4000 1_455 no H7B H4 2.5700 . no H7B H2 2.4900 1_455 no H7C H13C 2.5300 2_665 no H7C H11 2.5900 1_545 no H8 O1 2.7200 2_765 no H9 H13C 2.5400 . no H9 C2 2.9100 2_765 no H9 H13A 2.1900 . no H9 C13 2.5500 . no H11 C5 2.7400 1_565 no H11 C14 2.5100 . no H11 C6 2.9400 1_565 no H11 H14A 2.4200 . no H11 C7 3.0700 1_565 no H11 H7C 2.5900 1_565 no H11 H14C 2.2200 . no H12 C4 2.9400 1_565 no H13A H9 2.1900 . no H13A C9 2.6700 . no H13B O1 2.8700 2_775 no H13B C20 2.9400 2_675 no H13B H14B 2.1000 . no H13C C11 3.0800 2_675 no H13C H7C 2.5300 2_665 no H13C H9 2.5400 . no H13C C9 2.9800 . no H14A H11 2.4200 . no H14A C9 3.0600 2_675 no H14A C11 2.8700 . no H14B H13B 2.1000 . no H14C C11 2.7000 . no H14C H11 2.2200 . no H15 O3 2.6900 1_455 no H16 H20A 2.4000 . no H16 C20 2.5200 . no H16 H20C 2.2400 . no H18 H21C 2.4400 . no H18 H21A 2.2600 . no H18 C6 3.0500 2_666 no H18 C4 2.9800 2_666 no H18 C5 2.8700 2_666 no H18 C21 2.5400 . no H19 C1 3.0200 2_666 no H20A H16 2.4000 . no H20A C16 2.8400 . no H20B H21B 2.1200 . no H20B C13 3.0700 2_675 no H20C H16 2.2400 . no H20C C16 2.7300 . no H21A C4 2.9100 2_666 no H21A C18 2.7200 . no H21A H18 2.2600 . no H21B H20B 2.1200 . no H21C C18 2.9000 . no H21C H18 2.4400 . no H21C C15 3.0300 2_666 no H21C C16 3.0600 2_666 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1 H1 N1 0.8400 1.8400 2.669(5) 170.00 . yes O3 H3 N3 0.8400 1.8300 2.663(4) 171.00 2_656 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C12 N1 C8 C9 0.0(7) no C8 N1 C12 C11 0.2(7) no C14 N2 C10 C9 178.6(4) no C13 N2 C10 C11 177.9(4) no C14 N2 C10 C11 -2.7(6) no C13 N2 C10 C9 -0.8(7) no C19 N3 C15 C16 -0.1(6) no C15 N3 C19 C18 0.1(6) no C21 N4 C17 C16 177.1(4) no C20 N4 C17 C18 176.0(4) no C21 N4 C17 C18 -2.2(6) no C20 N4 C17 C16 -4.7(6) no N1 C8 C9 C10 0.5(7) no C8 C9 C10 N2 177.5(4) no C8 C9 C10 C11 -1.2(6) no N2 C10 C11 C12 -177.3(4) no C9 C10 C11 C12 1.4(6) no C10 C11 C12 N1 -1.0(8) no N3 C15 C16 C17 -0.3(7) no C15 C16 C17 C18 0.7(6) no C15 C16 C17 N4 -178.7(4) no C16 C17 C18 C19 -0.7(6) no N4 C17 C18 C19 178.6(4) no C17 C18 C19 N3 0.3(6) no O1 C1 C2 C3 179.7(3) no C6 C1 C2 C3 -0.2(5) no O1 C1 C6 C5 179.8(3) no C2 C1 C6 C5 -0.4(5) no C1 C2 C3 O3 -179.7(3) no C1 C2 C3 C4 0.8(5) no O3 C3 C4 C5 179.6(3) no C2 C3 C4 C5 -0.9(5) no C3 C4 C5 C6 0.3(5) no C3 C4 C5 C7 -179.7(3) no C4 C5 C6 C1 0.4(5) no C7 C5 C6 C1 -179.6(3) no