#------------------------------------------------------------------------------ #$Date: 2019-10-11 11:06:48 +0300 (Fri, 11 Oct 2019) $ #$Revision: 219284 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/45/7234549.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_7234549 loop_ _publ_author_name 'Martin Ipuy' 'Yuan-Yuan Liao' 'Erwann Jeanneau' 'Patrice L. Baldeck' 'Yann Bretonniere' 'Chantal Andraud' _publ_section_title ; Solid state red biphotonic excited emission from small dipolar fluorophores ; _journal_name_full 'Journal of Materials Chemistry C' _journal_page_first 766 _journal_page_last 779 _journal_paper_doi 10.1039/C5TC03465E _journal_volume 4 _journal_year 2016 _chemical_absolute_configuration . _chemical_formula_moiety 'C21 H19 N3 O4' _chemical_formula_sum 'C21 H19 N3 O4' _chemical_formula_weight 377.40 _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _cell_angle_alpha 90 _cell_angle_beta 92.397(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.229(2) _cell_length_b 7.5088(7) _cell_length_c 16.6390(10) _cell_measurement_reflns_used 7073 _cell_measurement_temperature 150 _cell_measurement_theta_max 66.8750 _cell_measurement_theta_min 2.7900 _cell_volume 1901.0(3) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _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 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 150 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.4685 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method \w _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.098 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 17984 _diffrn_reflns_theta_full 67.047 _diffrn_reflns_theta_max 67.047 _diffrn_reflns_theta_min 3.855 _diffrn_source 'sealed X-ray tube' _diffrn_source_type 'Enhance Ultra (Cu) X-ray Source' _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.765 _exptl_absorpt_correction_T_max 0.940 _exptl_absorpt_correction_T_min 0.755 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_description neddle _exptl_crystal_F_000 792 _exptl_crystal_preparation Luminescent _exptl_crystal_size_max 0.351 _exptl_crystal_size_mid 0.053 _exptl_crystal_size_min 0.048 _refine_diff_density_max 0.34 _refine_diff_density_min -0.35 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.0740 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 253 _refine_ls_number_reflns 3336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0693 _refine_ls_shift/su_max 0.0004823 _refine_ls_shift/su_mean 0.0001084 _refine_ls_structure_factor_coef Fsqd _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: 0.148E+04 0.232E+04 0.118E+04 291. ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1412 _refine_ls_wR_factor_gt 0.1247 _refine_ls_wR_factor_ref 0.1412 _reflns_limit_h_max 18 _reflns_limit_h_min -18 _reflns_limit_k_max 8 _reflns_limit_k_min 0 _reflns_limit_l_max 19 _reflns_limit_l_min 0 _reflns_number_gt 2852 _reflns_number_total 3353 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 2.86 _oxford_diffrn_Wilson_scale 0.03 _oxford_refine_ls_r_factor_ref 0.0762 _oxford_refine_ls_scale 5.50(12) _oxford_reflns_number_all 3336 _oxford_reflns_threshold_expression_ref I>0.0\s(I) _cod_data_source_file J-Mater-Chem-C-2016-4-766.cif _cod_data_source_block 5 _cod_original_sg_symbol_H-M 'P 1 21/n 1 ' _cod_database_code 7234549 _iucr_refine_instruction_details_constraints ; # # Punched on 04/04/14 at 09:36:07 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 9,X'S) H ( 91,X'S) H ( 92,X'S) H ( 93,X'S) RIDE C ( 12,X'S) H ( 122,X'S) H ( 121,X'S) H ( 123,X'S) RIDE C ( 15,X'S) H ( 152,X'S) H ( 153,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 27,X'S) H ( 271,X'S) H ( 273,X'S) H ( 272,X'S) RIDE C ( 28,X'S) H ( 282,X'S) H ( 281,X'S) H ( 283,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 04/04/14 at 09:36:07 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.30660(12) 0.4110(2) 0.64675(10) 0.0301 1.0000 Uani . . . . . . C2 C 0.31177(17) 0.3927(3) 0.55850(14) 0.0268 1.0000 Uani . . . . . . C3 C 0.36950(16) 0.5468(3) 0.53720(14) 0.0244 1.0000 Uani . . . . . . C4 C 0.39588(16) 0.5917(3) 0.45827(14) 0.0253 1.0000 Uani . . . . . . C5 C 0.37436(16) 0.4969(3) 0.39093(14) 0.0256 1.0000 Uani . . . . . . C6 C 0.39863(16) 0.5357(3) 0.31002(13) 0.0237 1.0000 Uani . . . . . . C7 C 0.37042(17) 0.4173(3) 0.24772(14) 0.0247 1.0000 Uani . . . . . . O8 O 0.31858(12) 0.2778(2) 0.26766(11) 0.0307 1.0000 Uani . . . . . . C9 C 0.34181(19) 0.1043(3) 0.23983(17) 0.0357 1.0000 Uani . . . . . . H91 H 0.3231 0.0158 0.2782 0.0540 1.0000 Uiso R . . . . . H92 H 0.4048 0.0956 0.2362 0.0545 1.0000 Uiso R . . . . . H93 H 0.3126 0.0785 0.1880 0.0545 1.0000 Uiso R . . . . . C10 C 0.39147(17) 0.4513(3) 0.16909(14) 0.0265 1.0000 Uani . . . . . . O11 O 0.36194(13) 0.3381(3) 0.10819(10) 0.0344 1.0000 Uani . . . . . . C12 C 0.2898(2) 0.4061(5) 0.06306(19) 0.0497 1.0000 Uani . . . . . . H122 H 0.2776 0.3267 0.0174 0.0740 1.0000 Uiso R . . . . . H121 H 0.3009 0.5256 0.0454 0.0743 1.0000 Uiso R . . . . . H123 H 0.2394 0.4044 0.0968 0.0743 1.0000 Uiso R . . . . . C13 C 0.44246(18) 0.5996(3) 0.15118(14) 0.0269 1.0000 Uani . . . . . . O14 O 0.45947(14) 0.6181(3) 0.07216(10) 0.0383 1.0000 Uani . . . . . . C15 C 0.5093(2) 0.7686(4) 0.04955(17) 0.0418 1.0000 Uani . . . . . . H152 H 0.5135 0.7664 -0.0084 0.0631 1.0000 Uiso R . . . . . H153 H 0.5682 0.7642 0.0743 0.0625 1.0000 Uiso R . . . . . H151 H 0.4790 0.8777 0.0635 0.0623 1.0000 Uiso R . . . . . C16 C 0.46971(16) 0.7168(3) 0.21170(15) 0.0287 1.0000 Uani . . . . . . C17 C 0.44715(16) 0.6853(3) 0.28934(14) 0.0267 1.0000 Uani . . . . . . H171 H 0.4640 0.7682 0.3297 0.0320 1.0000 Uiso R . . . . . H161 H 0.5029 0.8189 0.1997 0.0344 1.0000 Uiso R . . . . . H51 H 0.3412 0.3899 0.3980 0.0299 1.0000 Uiso R . . . . . H41 H 0.4302 0.6963 0.4527 0.0309 1.0000 Uiso R . . . . . C18 C 0.39216(16) 0.6379(3) 0.60602(14) 0.0256 1.0000 Uani . . . . . . C19 C 0.35205(16) 0.5526(3) 0.67241(14) 0.0256 1.0000 Uani . . . . . . C20 C 0.35499(17) 0.5925(3) 0.75303(14) 0.0274 1.0000 Uani . . . . . . C21 C 0.39821(18) 0.7460(4) 0.78518(15) 0.0324 1.0000 Uani . . . . . . N22 N 0.43067(18) 0.8697(4) 0.81387(15) 0.0484 1.0000 Uani . . . . . . C23 C 0.31233(18) 0.4794(4) 0.80728(14) 0.0321 1.0000 Uani . . . . . . N24 N 0.27918(19) 0.3871(4) 0.85153(14) 0.0466 1.0000 Uani . . . . . . C25 C 0.44902(17) 0.7874(3) 0.60978(14) 0.0276 1.0000 Uani . . . . . . N26 N 0.49689(17) 0.9054(3) 0.60885(14) 0.0387 1.0000 Uani . . . . . . C27 C 0.35257(18) 0.2123(4) 0.54561(15) 0.0312 1.0000 Uani . . . . . . H271 H 0.3562 0.1888 0.4890 0.0471 1.0000 Uiso R . . . . . H273 H 0.4105 0.2098 0.5707 0.0463 1.0000 Uiso R . . . . . H272 H 0.3199 0.1179 0.5696 0.0465 1.0000 Uiso R . . . . . C28 C 0.21762(18) 0.4083(4) 0.52472(16) 0.0351 1.0000 Uani . . . . . . H282 H 0.2152 0.3968 0.4675 0.0527 1.0000 Uiso R . . . . . H281 H 0.1821 0.3155 0.5463 0.0528 1.0000 Uiso R . . . . . H283 H 0.1951 0.5202 0.5384 0.0519 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 0.0404(10) 0.0333(10) 0.0168(8) -0.0011(8) 0.0036(7) -0.0076(8) C2 0.0330(13) 0.0336(14) 0.0139(11) -0.0049(10) 0.0005(9) -0.0030(10) C3 0.0279(12) 0.0275(12) 0.0177(11) -0.0003(10) -0.0003(9) 0.0055(10) C4 0.0308(13) 0.0286(12) 0.0164(11) 0.0014(10) 0.0008(9) 0.0003(10) C5 0.0301(12) 0.0277(13) 0.0188(11) 0.0012(10) -0.0001(9) 0.0029(10) C6 0.0314(13) 0.0248(12) 0.0146(11) 0.0013(9) -0.0024(9) 0.0028(10) C7 0.0322(13) 0.0226(12) 0.0194(12) -0.0002(10) 0.0004(10) -0.0013(9) O8 0.0384(10) 0.0260(9) 0.0283(9) -0.0044(7) 0.0067(7) -0.0052(8) C9 0.0433(16) 0.0266(14) 0.0371(15) -0.0012(11) 0.0030(12) -0.0037(12) C10 0.0379(14) 0.0250(12) 0.0163(11) -0.0035(9) -0.0016(10) 0.0002(10) O11 0.0516(12) 0.0327(10) 0.0186(9) -0.0047(8) -0.0018(8) -0.0050(9) C12 0.058(2) 0.0493(19) 0.0407(17) -0.0107(15) -0.0153(15) -0.0030(16) C13 0.0359(13) 0.0310(13) 0.0138(11) 0.0010(10) 0.0010(9) 0.0006(11) O14 0.0567(13) 0.0384(11) 0.0207(9) 0.0001(8) 0.0106(8) -0.0102(9) C15 0.0523(17) 0.0431(17) 0.0307(15) 0.0068(13) 0.0106(13) -0.0105(14) C16 0.0325(13) 0.0277(13) 0.0257(13) 0.0001(10) -0.0004(10) -0.0030(11) C17 0.0335(13) 0.0261(13) 0.0202(12) -0.0010(10) -0.0026(9) -0.0013(10) C18 0.0334(13) 0.0276(13) 0.0156(11) -0.0010(9) 0.0005(9) 0.0021(10) C19 0.0300(13) 0.0284(13) 0.0185(11) -0.0039(10) 0.0011(9) 0.0011(10) C20 0.0335(14) 0.0317(13) 0.0172(11) -0.0021(10) 0.0031(10) -0.0017(10) C21 0.0356(14) 0.0399(15) 0.0221(12) -0.0040(11) 0.0039(10) -0.0059(12) N22 0.0547(16) 0.0534(17) 0.0378(14) -0.0118(13) 0.0108(12) -0.0167(14) C23 0.0395(14) 0.0378(15) 0.0193(12) -0.0056(11) 0.0024(11) -0.0028(12) N24 0.0593(17) 0.0519(17) 0.0290(13) -0.0015(12) 0.0069(12) -0.0155(13) C25 0.0365(13) 0.0276(13) 0.0188(12) -0.0031(10) 0.0026(10) 0.0042(11) N26 0.0484(15) 0.0330(13) 0.0348(13) -0.0001(10) 0.0026(11) -0.0066(11) C27 0.0404(14) 0.0301(14) 0.0231(12) -0.0001(11) 0.0011(10) -0.0020(11) C28 0.0328(14) 0.0446(16) 0.0279(13) -0.0020(12) 0.0007(11) 0.0001(12) 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 0.0181 0.0091 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 0.0311 0.0180 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 0.0492 0.0322 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' 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 . O1 . C19 . 110.14(18) yes O1 . C2 . C3 . 102.60(18) yes O1 . C2 . C27 . 105.28(19) yes C3 . C2 . C27 . 114.1(2) yes O1 . C2 . C28 . 105.7(2) yes C3 . C2 . C28 . 113.8(2) yes C27 . C2 . C28 . 113.8(2) yes C2 . C3 . C4 . 125.9(2) yes C2 . C3 . C18 . 108.5(2) yes C4 . C3 . C18 . 125.6(2) yes C3 . C4 . C5 . 124.6(2) yes C3 . C4 . H41 . 117.5 no C5 . C4 . H41 . 117.9 no C4 . C5 . C6 . 127.1(2) yes C4 . C5 . H51 . 116.6 no C6 . C5 . H51 . 116.2 no C5 . C6 . C7 . 118.3(2) yes C5 . C6 . C17 . 123.5(2) yes C7 . C6 . C17 . 118.1(2) yes C6 . C7 . O8 . 117.7(2) yes C6 . C7 . C10 . 120.0(2) yes O8 . C7 . C10 . 122.2(2) yes C7 . O8 . C9 . 117.88(19) yes O8 . C9 . H91 . 109.1 no O8 . C9 . H92 . 109.9 no H91 . C9 . H92 . 108.3 no O8 . C9 . H93 . 111.0 no H91 . C9 . H93 . 108.1 no H92 . C9 . H93 . 110.5 no C7 . C10 . O11 . 119.9(2) yes C7 . C10 . C13 . 120.1(2) yes O11 . C10 . C13 . 120.0(2) yes C10 . O11 . C12 . 113.1(2) yes O11 . C12 . H122 . 108.2 no O11 . C12 . H121 . 111.1 no H122 . C12 . H121 . 111.2 no O11 . C12 . H123 . 107.9 no H122 . C12 . H123 . 108.3 no H121 . C12 . H123 . 110.0 no C10 . C13 . O14 . 114.7(2) yes C10 . C13 . C16 . 120.2(2) yes O14 . C13 . C16 . 125.1(2) yes C13 . O14 . C15 . 117.6(2) yes O14 . C15 . H152 . 108.0 no O14 . C15 . H153 . 110.7 no H152 . C15 . H153 . 108.8 no O14 . C15 . H151 . 110.0 no H152 . C15 . H151 . 107.7 no H153 . C15 . H151 . 111.5 no C13 . C16 . C17 . 119.7(2) yes C13 . C16 . H161 . 120.5 no C17 . C16 . H161 . 119.8 no C6 . C17 . C16 . 121.8(2) yes C6 . C17 . H171 . 119.2 no C16 . C17 . H171 . 119.0 no C3 . C18 . C19 . 108.7(2) yes C3 . C18 . C25 . 124.5(2) yes C19 . C18 . C25 . 126.8(2) yes C18 . C19 . O1 . 110.0(2) yes C18 . C19 . C20 . 131.1(2) yes O1 . C19 . C20 . 118.9(2) yes C19 . C20 . C21 . 122.7(2) yes C19 . C20 . C23 . 119.7(2) yes C21 . C20 . C23 . 117.6(2) yes C20 . C21 . N22 . 177.0(3) yes C20 . C23 . N24 . 178.9(3) yes C18 . C25 . N26 . 176.2(3) yes C2 . C27 . H271 . 110.1 no C2 . C27 . H273 . 109.4 no H271 . C27 . H273 . 109.5 no C2 . C27 . H272 . 112.3 no H271 . C27 . H272 . 108.8 no H273 . C27 . H272 . 106.7 no C2 . C28 . H282 . 111.0 no C2 . C28 . H281 . 110.0 no H282 . C28 . H281 . 108.0 no C2 . C28 . H283 . 109.1 no H282 . C28 . H283 . 108.8 no H281 . C28 . H283 . 110.0 no 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 . C2 . 1.480(3) yes O1 . C19 . 1.329(3) yes C2 . C3 . 1.505(3) yes C2 . C27 . 1.509(4) yes C2 . C28 . 1.523(4) yes C3 . C4 . 1.430(3) yes C3 . C18 . 1.366(3) yes C4 . C5 . 1.356(3) yes C4 . H41 . 0.951 no C5 . C6 . 1.441(3) yes C5 . H51 . 0.959 no C6 . C7 . 1.418(3) yes C6 . C17 . 1.396(3) yes C7 . O8 . 1.361(3) yes C7 . C10 . 1.384(3) yes O8 . C9 . 1.432(3) yes C9 . H91 . 0.973 no C9 . H92 . 0.965 no C9 . H93 . 0.973 no C10 . O11 . 1.383(3) yes C10 . C13 . 1.397(4) yes O11 . C12 . 1.401(4) yes C12 . H122 . 0.977 no C12 . H121 . 0.962 no C12 . H123 . 0.969 no C13 . O14 . 1.358(3) yes C13 . C16 . 1.388(4) yes O14 . C15 . 1.421(3) yes C15 . H152 . 0.969 no C15 . H153 . 0.972 no C15 . H151 . 0.973 no C16 . C17 . 1.371(3) yes C16 . H161 . 0.945 no C17 . H171 . 0.943 no C18 . C19 . 1.435(3) yes C18 . C25 . 1.418(4) yes C19 . C20 . 1.373(3) yes C20 . C21 . 1.421(4) yes C20 . C23 . 1.416(4) yes C21 . N22 . 1.146(4) yes C23 . N24 . 1.144(4) yes C25 . N26 . 1.148(3) yes C27 . H271 . 0.962 no C27 . H273 . 0.961 no C27 . H272 . 0.962 no C28 . H282 . 0.955 no C28 . H281 . 0.961 no C28 . H283 . 0.939 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 C16 . H161 . N22 2_676 167.60(8) 0.945 2.561 3.490(4) yes