#------------------------------------------------------------------------------ #$Date: 2024-01-06 09:54:06 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288775 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247647.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_7247647 loop_ _publ_author_name 'Ovcharenko, Victor' 'Fursova, Elena' 'Letyagin, Gleb' 'Morozov, Vitaly' 'Bogomyakov, Artem' 'Romanenko, Galina' _publ_section_title ; Alternating [ML2(MeOH)2] and [ML2(EtOH)2] layers in low-temperature ferromagnets [ML2(MeOH)2][ML2(EtOH)2] (M = CoII, NiII or CoII0.5NiII0.5) ; _journal_issue 44 _journal_name_full CrystEngComm _journal_page_first 6194 _journal_page_last 6203 _journal_paper_doi 10.1039/D3CE00912B _journal_volume 25 _journal_year 2023 _chemical_formula_sum 'C22 H34 F6 N4 Ni O6' _chemical_formula_weight 623.24 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _audit_block_doi 10.5517/ccdc.csd.cc2bjd1b _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2022-03-22 deposited with the CCDC. 2023-10-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 118.800(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.9504(11) _cell_length_b 15.8017(18) _cell_length_c 11.5358(17) _cell_measurement_reflns_used 9037 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 67.72 _cell_measurement_theta_min 4.37 _cell_volume 1429.7(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_unetI/netI 0.0305 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 13028 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 67.719 _diffrn_reflns_theta_min 5.194 _exptl_absorpt_coefficient_mu 1.716 _exptl_absorpt_correction_type none _exptl_crystal_colour light_green _exptl_crystal_density_diffrn 1.448 _exptl_crystal_description bulk _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.433 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.043 _refine_ls_extinction_coef 0.0038(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 247 _refine_ls_number_reflns 2560 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0320 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.5130P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0903 _refine_ls_wR_factor_ref 0.0915 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2448 _reflns_number_total 2560 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00912b1.cif _cod_data_source_block nime _cod_depositor_comments 'Adding full bibliography for 7247645--7247650.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247647 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; TITL nimes in P2(1)/c nime.res created by SHELXL-2018/3 at 20:54:01 on 07-Jun-2018 CELL 1.54178 8.95040 15.80170 11.53582 90.0000 118.7996 90.0000 ZERR 2.00 0.00110 0.00180 0.00170 0.0000 0.0037 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O F NI UNIT 44 68 8 12 12 2 TEMP 23.000 l.s. 20 fmap 2 plan 20 htab EQIV $1 -x, -y, -z HTAB C51 O1_$1 HTAB C52 O1_$1 EQIV $2 -x, y+1/2, -z-1/2 HTAB O01 O11_$2 acta WGHT 0.050700 0.513000 EXTI 0.003786 FVAR 0.23931 NI 6 0.000000 0.000000 0.000000 10.50000 0.03150 0.02366 = 0.02942 -0.00256 0.01293 0.00003 O1 4 0.235718 -0.014358 0.150613 11.00000 0.03718 0.03901 = 0.03746 -0.01080 0.00949 0.00564 C1 1 0.343720 -0.071793 0.167213 11.00000 0.03339 0.03530 = 0.03201 0.00124 0.01475 0.00170 C11 1 0.508078 -0.062352 0.297179 11.00000 0.03731 0.05074 = 0.03920 -0.00684 0.01324 0.00237 F1 5 0.620212 -0.124068 0.322008 11.00000 0.04921 0.08406 = 0.05146 -0.00758 0.00589 0.02735 F2 5 0.479069 -0.060486 0.399204 11.00000 0.05847 0.13252 = 0.03492 -0.01518 0.01502 0.01390 F3 5 0.587778 0.008432 0.299921 11.00000 0.05686 0.07423 = 0.09843 0.00113 0.00068 -0.02520 C2 1 0.329157 -0.136650 0.085012 11.00000 0.03946 0.03432 = 0.03567 0.00099 0.01735 0.00768 H2 2 0.417064 -0.175458 0.112099 11.00000 0.04252 C3 1 0.184161 -0.150227 -0.040703 11.00000 0.04231 0.02666 = 0.03564 -0.00154 0.02024 0.00160 C4 1 0.187525 -0.222979 -0.125188 11.00000 0.05251 0.03305 = 0.04196 -0.00855 0.01891 0.00561 C41 1 0.331940 -0.215310 -0.158687 11.00000 0.06953 0.07165 = 0.06219 -0.02206 0.03814 0.00529 H411 2 0.308902 -0.252474 -0.222539 11.00000 0.07878 H412 2 0.441936 -0.230174 -0.081532 11.00000 0.08072 H413 2 0.327876 -0.164569 -0.195976 11.00000 0.07748 C42 1 0.187582 -0.308998 -0.065185 11.00000 0.08914 0.03230 = 0.06780 -0.00375 0.02871 0.00687 H421 2 0.291166 -0.317136 0.011175 11.00000 0.06597 H422 2 0.169339 -0.351509 -0.125750 11.00000 0.08659 H423 2 0.094157 -0.312890 -0.042156 11.00000 0.08672 N11 3 0.024660 -0.207550 -0.243172 11.00000 0.05754 0.03765 = 0.04232 -0.01664 0.01453 0.00433 O11 4 -0.027734 -0.248269 -0.351710 11.00000 0.08352 0.04807 = 0.04972 -0.02504 0.01658 0.00561 C5 1 -0.072689 -0.136541 -0.228531 11.00000 0.04638 0.03418 = 0.03828 -0.01466 0.00966 0.00193 C51 1 -0.103398 -0.070701 -0.333568 11.00000 0.07570 0.05323 = 0.03251 -0.00608 0.01178 0.01624 H511 2 -0.161584 -0.095515 -0.411426 11.00000 0.07557 H512 2 -0.167577 -0.024118 -0.325388 11.00000 0.07455 H513 2 0.001562 -0.050376 -0.322912 11.00000 0.09242 C52 1 -0.235767 -0.171130 -0.237484 11.00000 0.05003 0.05177 = 0.08658 -0.03006 0.02068 -0.01013 H521 2 -0.298098 -0.204562 -0.321642 11.00000 0.07901 H522 2 -0.294877 -0.129094 -0.226927 11.00000 0.10181 H523 2 -0.209891 -0.210670 -0.169323 11.00000 0.08247 N1 3 0.045716 -0.105101 -0.094454 11.00000 0.03853 0.02577 = 0.03134 -0.00515 0.01392 -0.00024 O01 4 0.088243 0.083063 -0.095663 11.00000 0.06029 0.03613 = 0.06712 0.00936 0.04135 0.00098 H01 2 0.053990 0.132046 -0.106731 11.00000 0.07785 C01 1 0.249959 0.080406 -0.087510 11.00000 0.07854 0.06677 = 0.12784 0.01992 0.07629 0.00205 H011 2 0.284043 0.029391 -0.091565 11.00000 0.12302 H012 2 0.263356 0.115999 -0.139631 11.00000 0.10709 H013 2 0.328231 0.110420 -0.005578 11.00000 0.15806 HKLF 4 REM nimes in P2(1)/c REM wR2 = 0.0915, GooF = S = 1.032, Restrained GooF = 1.032 for all data REM R1 = 0.0320 for 2448 Fo > 4sig(Fo) and 0.0330 for all 2560 data REM 247 parameters refined using 0 restraints END WGHT 0.0457 0.5704 REM Instructions for potential hydrogen bonds HTAB C51 O1_$1 HTAB C52 O1_$1 HTAB O01 O11_$2 REM Highest difference peak 0.433, deepest hole -0.285, 1-sigma level 0.043 Q1 1 0.5146 -0.0086 0.3810 11.00000 0.05 0.43 Q2 1 -0.0747 -0.2750 -0.3070 11.00000 0.05 0.28 Q3 1 0.1888 -0.1865 -0.0812 11.00000 0.05 0.24 Q4 1 0.6286 -0.0710 0.2949 11.00000 0.05 0.23 Q5 1 0.0334 -0.0644 -0.0608 11.00000 0.05 0.22 Q6 1 -0.0182 -0.1194 -0.1609 11.00000 0.05 0.22 Q7 1 0.2878 -0.0064 0.1340 11.00000 0.05 0.21 Q8 1 0.1380 0.0993 -0.0134 11.00000 0.05 0.17 Q9 1 0.3130 -0.1209 0.1392 11.00000 0.05 0.17 Q10 1 0.3525 -0.0894 0.1071 11.00000 0.05 0.17 Q11 1 0.5579 -0.1335 0.3528 11.00000 0.05 0.16 Q12 1 0.2437 -0.1524 0.0351 11.00000 0.05 0.16 Q13 1 0.0894 -0.1348 -0.0558 11.00000 0.05 0.16 Q14 1 0.4234 -0.0753 0.2304 11.00000 0.05 0.16 Q15 1 0.3523 0.0496 0.0058 11.00000 0.05 0.15 Q16 1 0.1852 -0.2652 -0.0958 11.00000 0.05 0.15 Q17 1 -0.0351 -0.2241 -0.2059 11.00000 0.05 0.15 Q18 1 0.5196 -0.1122 0.3877 11.00000 0.05 0.15 Q19 1 0.5899 0.0364 0.2384 11.00000 0.05 0.14 Q20 1 0.0797 0.0390 -0.0640 11.00000 0.05 0.13 ; _shelx_res_checksum 4606 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni 0.000000 0.000000 0.000000 0.02892(15) Uani 1 2 d S . P . . O1 O 0.23572(15) -0.01436(7) 0.15061(11) 0.0414(3) Uani 1 1 d . . . . . C1 C 0.34372(19) -0.07179(10) 0.16721(14) 0.0340(3) Uani 1 1 d . . . . . C11 C 0.5081(2) -0.06235(12) 0.29718(16) 0.0446(4) Uani 1 1 d . . . . . F1 F 0.62021(15) -0.12407(9) 0.32201(11) 0.0693(4) Uani 1 1 d . . . . . F2 F 0.47907(16) -0.06049(11) 0.39920(11) 0.0784(4) Uani 1 1 d . . . . . F3 F 0.58778(19) 0.00843(9) 0.29992(18) 0.0919(5) Uani 1 1 d . . . . . C2 C 0.3292(2) -0.13665(10) 0.08501(15) 0.0368(3) Uani 1 1 d . . . . . H2 H 0.417(3) -0.1755(13) 0.1121(19) 0.043(5) Uiso 1 1 d . . . . . C3 C 0.1842(2) -0.15023(9) -0.04070(15) 0.0343(3) Uani 1 1 d . . . . . C4 C 0.1875(2) -0.22298(10) -0.12519(17) 0.0441(4) Uani 1 1 d . . . . . C41 C 0.3319(3) -0.21531(18) -0.1587(3) 0.0651(6) Uani 1 1 d . . . . . H411 H 0.309(4) -0.2525(18) -0.223(3) 0.079(8) Uiso 1 1 d . . . . . H412 H 0.442(4) -0.2302(17) -0.082(3) 0.081(8) Uiso 1 1 d . . . . . H413 H 0.328(4) -0.165(2) -0.196(3) 0.077(8) Uiso 1 1 d . . . . . C42 C 0.1876(4) -0.30900(13) -0.0652(3) 0.0669(6) Uani 1 1 d . . . . . H421 H 0.291(3) -0.3171(16) 0.011(3) 0.066(7) Uiso 1 1 d . . . . . H422 H 0.169(4) -0.3515(19) -0.126(3) 0.087(8) Uiso 1 1 d . . . . . H423 H 0.094(4) -0.3129(19) -0.042(3) 0.087(9) Uiso 1 1 d . . . . . N11 N 0.0247(2) -0.20755(9) -0.24317(15) 0.0498(4) Uani 1 1 d . . . . . O11 O -0.0277(2) -0.24827(9) -0.35171(13) 0.0669(4) Uani 1 1 d . . . . . C5 C -0.0727(2) -0.13654(11) -0.22853(16) 0.0441(4) Uani 1 1 d . . . . . C51 C -0.1034(4) -0.07070(14) -0.33357(19) 0.0598(6) Uani 1 1 d . . . . . H511 H -0.162(3) -0.0955(17) -0.411(3) 0.076(7) Uiso 1 1 d . . . . . H512 H -0.168(4) -0.0241(19) -0.325(3) 0.075(7) Uiso 1 1 d . . . . . H513 H 0.002(4) -0.050(2) -0.323(3) 0.092(10) Uiso 1 1 d . . . . . C52 C -0.2358(3) -0.17113(16) -0.2375(3) 0.0679(7) Uani 1 1 d . . . . . H521 H -0.298(4) -0.2046(18) -0.322(3) 0.079(8) Uiso 1 1 d . . . . . H522 H -0.295(4) -0.129(2) -0.227(3) 0.102(10) Uiso 1 1 d . . . . . H523 H -0.210(4) -0.211(2) -0.169(3) 0.082(9) Uiso 1 1 d . . . . . N1 N 0.04572(17) -0.10510(8) -0.09445(12) 0.0331(3) Uani 1 1 d . . . . . O01 O 0.08824(18) 0.08306(8) -0.09566(14) 0.0501(3) Uani 1 1 d . . . . . H01 H 0.054(4) 0.1320(18) -0.107(3) 0.078(8) Uiso 1 1 d . . . . . C01 C 0.2500(4) 0.0804(2) -0.0875(4) 0.0799(8) Uani 1 1 d . . . . . H011 H 0.284(5) 0.029(3) -0.092(4) 0.123(13) Uiso 1 1 d . . . . . H012 H 0.263(4) 0.116(2) -0.140(4) 0.107(11) Uiso 1 1 d . . . . . H013 H 0.328(6) 0.110(3) -0.006(5) 0.158(19) Uiso 1 1 d . . . . . 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 Ni 0.0315(2) 0.0237(2) 0.0294(2) -0.00256(12) 0.01293(16) 0.00003(12) O1 0.0372(6) 0.0390(6) 0.0375(6) -0.0108(5) 0.0095(5) 0.0056(5) C1 0.0334(7) 0.0353(8) 0.0320(7) 0.0012(6) 0.0148(6) 0.0017(6) C11 0.0373(8) 0.0507(10) 0.0392(8) -0.0068(7) 0.0132(7) 0.0024(7) F1 0.0492(6) 0.0841(9) 0.0515(6) -0.0076(6) 0.0059(5) 0.0274(6) F2 0.0585(7) 0.1325(13) 0.0349(6) -0.0152(6) 0.0150(5) 0.0139(8) F3 0.0569(8) 0.0742(9) 0.0984(11) 0.0011(7) 0.0007(8) -0.0252(7) C2 0.0395(8) 0.0343(8) 0.0357(8) 0.0010(6) 0.0174(7) 0.0077(6) C3 0.0423(8) 0.0267(7) 0.0356(7) -0.0015(6) 0.0202(7) 0.0016(6) C4 0.0525(10) 0.0331(8) 0.0420(9) -0.0085(7) 0.0189(8) 0.0056(7) C41 0.0695(14) 0.0717(15) 0.0622(13) -0.0221(12) 0.0381(12) 0.0053(12) C42 0.0891(18) 0.0323(10) 0.0678(14) -0.0037(9) 0.0287(14) 0.0069(10) N11 0.0575(9) 0.0376(7) 0.0423(8) -0.0166(6) 0.0145(7) 0.0043(7) O11 0.0835(10) 0.0481(8) 0.0497(8) -0.0250(6) 0.0166(7) 0.0056(7) C5 0.0464(9) 0.0342(8) 0.0383(8) -0.0147(6) 0.0097(7) 0.0019(7) C51 0.0757(15) 0.0532(12) 0.0325(9) -0.0061(8) 0.0118(9) 0.0162(11) C52 0.0500(12) 0.0518(12) 0.0866(17) -0.0301(13) 0.0207(11) -0.0101(10) N1 0.0385(7) 0.0258(6) 0.0313(6) -0.0051(5) 0.0139(5) -0.0002(5) O01 0.0603(8) 0.0361(6) 0.0671(8) 0.0094(6) 0.0413(7) 0.0010(6) C01 0.0785(17) 0.0668(16) 0.128(3) 0.0199(17) 0.0763(19) 0.0020(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ni O1 180.00(13) 3 . ? O1 Ni O01 91.21(6) 3 3 ? O1 Ni O01 88.79(6) . 3 ? O1 Ni O01 88.79(6) 3 . ? O1 Ni O01 91.21(6) . . ? O01 Ni O01 180.0 3 . ? O1 Ni N1 91.51(5) 3 . ? O1 Ni N1 88.49(5) . . ? O01 Ni N1 89.72(5) 3 . ? O01 Ni N1 90.28(5) . . ? O1 Ni N1 88.49(5) 3 3 ? O1 Ni N1 91.51(5) . 3 ? O01 Ni N1 90.28(5) 3 3 ? O01 Ni N1 89.72(5) . 3 ? N1 Ni N1 180.0 . 3 ? C1 O1 Ni 128.31(10) . . ? O1 C1 C2 128.52(15) . . ? O1 C1 C11 112.52(13) . . ? C2 C1 C11 118.96(14) . . ? F3 C11 F2 107.20(17) . . ? F3 C11 F1 105.89(16) . . ? F2 C11 F1 106.05(15) . . ? F3 C11 C1 111.24(15) . . ? F2 C11 C1 111.63(14) . . ? F1 C11 C1 114.36(14) . . ? C1 C2 C3 124.00(14) . . ? N1 C3 C2 126.60(13) . . ? N1 C3 C4 114.76(14) . . ? C2 C3 C4 118.62(14) . . ? N11 C4 C3 98.78(13) . . ? N11 C4 C41 109.83(17) . . ? C3 C4 C41 112.64(16) . . ? N11 C4 C42 110.75(17) . . ? C3 C4 C42 112.31(16) . . ? C41 C4 C42 111.81(19) . . ? O11 N11 C4 124.05(14) . . ? O11 N11 C5 122.34(15) . . ? C4 N11 C5 113.53(12) . . ? N1 C5 N11 102.10(13) . . ? N1 C5 C52 111.98(17) . . ? N11 C5 C52 108.64(16) . . ? N1 C5 C51 111.58(15) . . ? N11 C5 C51 108.59(16) . . ? C52 C5 C51 113.3(2) . . ? C3 N1 C5 110.69(12) . . ? C3 N1 Ni 123.88(10) . . ? C5 N1 Ni 125.43(10) . . ? C01 O01 Ni 125.63(15) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni O1 1.9974(12) 3 ? Ni O1 1.9974(12) . ? Ni O01 2.0986(12) 3 ? Ni O01 2.0986(12) . ? Ni N1 2.1313(12) . ? Ni N1 2.1313(12) 3 ? O1 C1 1.2714(19) . ? C1 C2 1.359(2) . ? C1 C11 1.520(2) . ? C11 F3 1.319(2) . ? C11 F2 1.322(2) . ? C11 F1 1.328(2) . ? C2 C3 1.421(2) . ? C3 N1 1.299(2) . ? C3 C4 1.517(2) . ? C4 N11 1.458(2) . ? C4 C41 1.522(3) . ? C4 C42 1.525(3) . ? N11 O11 1.2790(19) . ? N11 C5 1.479(2) . ? C5 N1 1.4775(19) . ? C5 C52 1.515(3) . ? C5 C51 1.518(3) . ? O01 C01 1.405(3) . ? 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 C51 H512 O1 0.97(3) 2.45(3) 3.174(3) 132(2) 3 yes C52 H522 O1 0.89(4) 2.40(3) 3.098(3) 135(3) 3 yes O01 H01 O11 0.82(3) 1.94(3) 2.7292(19) 162(3) 2_554 yes