# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Catherine E Housecroft' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Edwin Constable' ; ? # Address 2 ; ; ? # Footnote 2 ; 'Ana Hernandez Redondo' '' '' 'Markus Neuburger' '' '' 'Silvia Schaffner' '' '' _publ_contact_author_name 'Catherine E Housecroft' _publ_contact_author_email CATHERINE.HOUSECROFT@UNIBAS.CH _publ_section_title ; Copper(I) complexes of 6,6'-disubstituted 2,2' -bipyridine dicarboxylic acids: new complexes for incorporation into copper-based dye sensitised solar cells (DSCs). ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_name_full ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. ; _publ_contact_author_fax '+44 1865 285018' _publ_contact_author_phone '+44 1865 285024' # Check this file using the IUCr facility at: # http://journals.iucr.org/services/cif/checking/checkfull.html # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica C. The figures have been sent by mail. ; _publ_requested_category CO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' _publ_requested_journal 'Section C' # Attachment 'Dione.cif' data_ah067 _database_code_depnum_ccdc_archive 'CCDC 717559' _audit_creation_date 06-02-20 _audit_creation_method CRYSTALS_ver_12.24 _oxford_structure_analysis_title '2201204 ah067_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 37.4261(14) _cell_length_b 3.7745(2) _cell_length_c 18.0118(7) _cell_angle_alpha 90 _cell_angle_beta 118.174(2) _cell_angle_gamma 90 _cell_volume 2242.96(18) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 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' _cell_formula_units_Z 8 _chemical_formula_sum 'C14 H10 O4' _chemical_formula_moiety 'C14 H10 O4' _chemical_compound_source ? _chemical_formula_weight 242.23 _cell_measurement_reflns_used 4669 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.38 _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 # Sheldrick geometric definitions 0.99 0.99 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 173 _diffrn_reflns_number 9272 _reflns_number_total 2556 _diffrn_reflns_av_R_equivalents 0.026 # Number of reflections with Friedels Law is 2556 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2571 _diffrn_reflns_theta_min 3.332 _diffrn_reflns_theta_max 27.480 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.480 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -48 _diffrn_reflns_limit_h_max 47 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -48 _reflns_limit_h_max 42 _reflns_limit_k_min 0 _reflns_limit_k_max 4 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.20 _refine_diff_density_max 0.16 _refine_ls_number_reflns 1651 _refine_ls_number_restraints 0 _refine_ls_number_parameters 164 #_refine_ls_R_factor_ref 0.0470 _refine_ls_wR_factor_ref 0.0519 _refine_ls_goodness_of_fit_ref 1.1377 #_reflns_number_all 2547 _refine_ls_R_factor_all 0.0717 _refine_ls_wR_factor_all 0.0648 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.90u(I) _reflns_number_gt 1651 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_gt 0.0519 _refine_ls_shift/su_max 0.000379 # 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 F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _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: 1.71 1.87 1.20 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, (1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached 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 _atom_site_attached_hydrogens C1 C 0.31434(6) 0.4773(5) -0.15266(13) 0.0445 1.0000 Uani . . . . . . C2 C 0.30188(6) 0.3247(6) -0.22804(13) 0.0487 1.0000 Uani . . . . . . C3 C 0.33716(7) 0.2311(5) -0.23347(13) 0.0459 1.0000 Uani . . . . . . C4 C 0.36942(6) 0.3371(5) -0.16038(12) 0.0388 1.0000 Uani . . . . . . C5 C 0.41204(6) 0.3163(5) -0.13204(12) 0.0398 1.0000 Uani . . . . . . C6 C 0.44171(6) 0.4489(5) -0.06076(12) 0.0399 1.0000 Uani . . . . . . C7 C 0.48433(6) 0.4122(5) -0.04078(12) 0.0400 1.0000 Uani . . . . . . C8 C 0.43738(6) 0.3002(6) 0.21363(12) 0.0454 1.0000 Uani . . . . . . C9 C 0.44919(6) 0.1518(6) 0.16093(13) 0.0466 1.0000 Uani . . . . . . C10 C 0.41361(6) 0.0546(5) 0.08819(12) 0.0416 1.0000 Uani . . . . . . C11 C 0.38181(5) 0.1548(5) 0.10045(11) 0.0369 1.0000 Uani . . . . . . C12 C 0.33939(5) 0.1172(5) 0.04581(11) 0.0369 1.0000 Uani . . . . . . C13 C 0.30855(5) 0.2373(5) 0.05724(11) 0.0375 1.0000 Uani . . . . . . C14 C 0.26689(5) 0.1665(5) -0.00730(11) 0.0369 1.0000 Uani . . . . . . O1 O 0.35589(4) 0.4924(4) -0.10915(8) 0.0424 1.0000 Uani . . . . . . O2 O 0.49553(4) 0.2525(4) -0.08500(9) 0.0519 1.0000 Uani . . . . . . O3 O 0.39587(4) 0.3080(4) 0.17800(8) 0.0431 1.0000 Uani . . . . . . O4 O 0.25789(4) -0.0162(4) -0.06930(9) 0.0483 1.0000 Uani . . . . . . H11 H 0.2959 0.5714 -0.1313 0.0525 1.0000 Uiso R . . . . . H21 H 0.2732 0.2849 -0.2722 0.0571 1.0000 Uiso R . . . . . H31 H 0.3385 0.1064 -0.2811 0.0542 1.0000 Uiso R . . . . . H51 H 0.4208 0.1885 -0.1694 0.0497 1.0000 Uiso R . . . . . H61 H 0.4346 0.5735 -0.0205 0.0507 1.0000 Uiso R . . . . . H81 H 0.4562 0.3930 0.2710 0.0524 1.0000 Uiso R . . . . . H91 H 0.4776 0.1092 0.1716 0.0577 1.0000 Uiso R . . . . . H101 H 0.4117 -0.0554 0.0360 0.0494 1.0000 Uiso R . . . . . H121 H 0.3313 -0.0132 -0.0081 0.0446 1.0000 Uiso R . . . . . H131 H 0.3144 0.3757 0.1091 0.0457 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 0.0361(9) 0.0536(11) 0.0436(9) 0.0065(9) 0.0186(7) 0.0025(8) C2 0.0428(11) 0.0510(12) 0.0448(10) 0.0043(9) 0.0143(8) -0.0056(9) C3 0.0562(11) 0.0426(10) 0.0391(9) -0.0030(8) 0.0228(9) -0.0062(9) C4 0.0446(10) 0.0378(9) 0.0397(9) 0.0010(8) 0.0245(8) -0.0012(7) C5 0.0461(10) 0.0371(9) 0.0435(9) 0.0039(8) 0.0271(8) 0.0034(8) C6 0.0422(10) 0.0418(9) 0.0422(9) 0.0004(8) 0.0252(8) 0.0045(8) C7 0.0417(9) 0.0435(9) 0.0415(9) 0.0027(8) 0.0252(8) 0.0061(8) C8 0.0333(9) 0.0565(12) 0.0431(9) -0.0028(9) 0.0153(8) 0.0011(8) C9 0.0335(9) 0.0563(11) 0.0516(11) 0.0008(9) 0.0215(8) 0.0033(8) C10 0.0373(9) 0.0489(10) 0.0420(9) -0.0029(9) 0.0216(7) 0.0040(8) C11 0.0344(9) 0.0394(9) 0.0363(8) 0.0003(7) 0.0163(7) 0.0012(7) C12 0.0368(9) 0.0383(9) 0.0354(8) 0.0001(7) 0.0169(7) -0.0007(7) C13 0.0353(9) 0.0401(9) 0.0355(9) 0.0006(7) 0.0155(7) -0.0017(7) C14 0.0358(9) 0.0423(10) 0.0333(8) 0.0007(7) 0.0169(7) -0.0026(7) O1 0.0360(6) 0.0536(8) 0.0386(6) -0.0017(6) 0.0184(5) 0.0008(6) O2 0.0448(7) 0.0669(9) 0.0506(8) -0.0106(7) 0.0280(6) 0.0051(7) O3 0.0348(7) 0.0575(8) 0.0391(7) -0.0049(6) 0.0191(6) 0.0029(6) O4 0.0383(7) 0.0639(9) 0.0426(7) -0.0125(7) 0.0190(6) -0.0044(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3336(12) loop_ _oxford_twin_element_scale_factors 0.9042(15) 0.0958(15) 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 . 1.340(3) yes C1 . O1 . 1.373(2) yes C1 . H11 . 1.000 no C2 . C3 . 1.414(3) yes C2 . H21 . 1.000 no C3 . C4 . 1.360(3) yes C3 . H31 . 1.000 no C4 . C5 . 1.429(3) yes C4 . O1 . 1.376(2) yes C5 . C6 . 1.336(3) yes C5 . H51 . 1.000 no C6 . C7 . 1.467(3) yes C6 . H61 . 1.000 no C7 . C7 2_665 1.532(4) yes C7 . O2 . 1.220(2) yes C8 . C9 . 1.344(3) yes C8 . O3 . 1.373(2) yes C8 . H81 . 1.000 no C9 . C10 . 1.406(3) yes C9 . H91 . 1.000 no C10 . C11 . 1.363(2) yes C10 . H101 . 1.000 no C11 . C12 . 1.426(2) yes C11 . O3 . 1.367(2) yes C12 . C13 . 1.343(2) yes C12 . H121 . 1.000 no C13 . C14 . 1.464(2) yes C13 . H131 . 1.000 no C14 . C14 4_555 1.542(3) yes C14 . O4 . 1.217(2) yes 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 . O1 . 110.78(17) yes C2 . C1 . H11 . 124.758 no O1 . C1 . H11 . 124.457 no C1 . C2 . C3 . 106.74(18) yes C1 . C2 . H21 . 126.915 no C3 . C2 . H21 . 126.342 no C2 . C3 . C4 . 106.89(17) yes C2 . C3 . H31 . 127.104 no C4 . C3 . H31 . 125.994 no C3 . C4 . C5 . 131.33(18) yes C3 . C4 . O1 . 109.58(16) yes C5 . C4 . O1 . 119.09(16) yes C4 . C5 . C6 . 127.12(17) yes C4 . C5 . H51 . 116.768 no C6 . C5 . H51 . 116.112 no C5 . C6 . C7 . 120.96(16) yes C5 . C6 . H61 . 119.234 no C7 . C6 . H61 . 119.806 no C7 2_665 C7 . C6 . 116.49(18) yes C7 2_665 C7 . O2 . 119.8(2) yes C6 . C7 . O2 . 123.75(18) yes C9 . C8 . O3 . 110.83(17) yes C9 . C8 . H81 . 124.688 no O3 . C8 . H81 . 124.481 no C8 . C9 . C10 . 106.53(17) yes C8 . C9 . H91 . 127.269 no C10 . C9 . H91 . 126.167 no C9 . C10 . C11 . 106.98(17) yes C9 . C10 . H101 . 126.881 no C11 . C10 . H101 . 126.070 no C10 . C11 . C12 . 129.31(17) yes C10 . C11 . O3 . 109.80(16) yes C12 . C11 . O3 . 120.89(15) yes C11 . C12 . C13 . 128.16(17) yes C11 . C12 . H121 . 116.578 no C13 . C12 . H121 . 115.263 no C12 . C13 . C14 . 119.14(16) yes C12 . C13 . H131 . 119.543 no C14 . C13 . H131 . 121.309 no C14 4_555 C14 . C13 . 116.21(19) yes C14 4_555 C14 . O4 . 119.60(19) yes C13 . C14 . O4 . 124.18(16) yes C4 . O1 . C1 . 106.01(14) yes C8 . O3 . C11 . 105.86(14) yes # Attachment 'Ligand_H2_4_.cif' data_ah091_173k _database_code_depnum_ccdc_archive 'CCDC 717560' _audit_creation_date 06-10-25 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title '10251032 ah091_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 3.8591(6) _cell_length_b 8.1105(11) _cell_length_c 10.6066(16) _cell_angle_alpha 73.344(9) _cell_angle_beta 84.983(7) _cell_angle_gamma 77.881(10) _cell_volume 310.83(8) _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' 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 0.0061 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' 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' _cell_formula_units_Z 1 # Given Formula = C28 H20 N4 O8 # Dc = 2.89 Fooo = 142.00 Mu = 2.16 M = 270.24 # Found Formula = C14 H12 N2 O4 # Dc = 1.45 FOOO = 142.00 Mu = 1.09 M = 136.13 _chemical_formula_sum 'C14 H12 N2 O4' _chemical_formula_moiety 'C14 H12 N2 O4' _chemical_compound_source ? _chemical_formula_weight 272.26 _cell_measurement_reflns_used 1407 _cell_measurement_theta_min 1 _cell_measurement_theta_max 28 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_max 0.41 _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 142 _exptl_absorpt_coefficient_mu 0.109 # Sheldrick geometric approximatio 0.98 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 1.00 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 173 _diffrn_reflns_number 2789 _reflns_number_total 1468 _diffrn_reflns_av_R_equivalents 0.030 # Number of reflections with Friedels Law is 1468 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1485 _diffrn_reflns_theta_min 2.005 _diffrn_reflns_theta_max 27.893 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.335 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -5 _reflns_limit_h_max 5 _reflns_limit_k_min -9 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.34 _refine_diff_density_max 0.46 _refine_ls_number_reflns 1461 _refine_ls_number_restraints 0 _refine_ls_number_parameters 91 #_refine_ls_R_factor_ref 0.0834 _refine_ls_wR_factor_ref 0.1174 _refine_ls_goodness_of_fit_ref 1.0397 #_reflns_number_all 1461 _refine_ls_R_factor_all 0.0834 _refine_ls_wR_factor_all 0.1174 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 916 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_gt 0.0870 _refine_ls_shift/su_max 0.000057 # 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, 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: 16.1 20.8 6.42 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # 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 _atom_site_attached_hydrogens O1 O 0.6245(5) 0.2632(2) -0.47211(18) 0.0484 1.0000 Uani . . . . . . O2 O 0.2630(5) 0.4361(2) -0.36629(18) 0.0481 1.0000 Uani . . . . . . N1 N 0.2646(5) -0.1673(2) -0.06788(18) 0.0315 1.0000 Uani . . . . . . C1 C 0.6441(7) -0.3657(3) -0.1764(3) 0.0420 1.0000 Uani . . . . . . C2 C 0.4659(6) -0.1836(3) -0.1752(2) 0.0330 1.0000 Uani . . . . . . C3 C 0.5148(6) -0.0387(3) -0.2792(2) 0.0338 1.0000 Uani . . . . . . C4 C 0.3560(6) 0.1280(3) -0.2699(2) 0.0307 1.0000 Uani . . . . . . C5 C 0.4095(7) 0.2887(3) -0.3745(2) 0.0351 1.0000 Uani . . . . . . C6 C 0.1496(6) 0.1463(3) -0.1593(2) 0.0313 1.0000 Uani . . . . . . C7 C 0.1097(6) -0.0054(3) -0.0601(2) 0.0288 1.0000 Uani . . . . . . H1 H 0.6602 0.3624 -0.5227 0.0696 1.0000 Uiso R . . . . . H11 H 0.4746 -0.4393 -0.1642 0.0628 1.0000 Uiso R . . . . . H12 H 0.7991 -0.4150 -0.1024 0.0630 1.0000 Uiso R . . . . . H13 H 0.7832 -0.3674 -0.2572 0.0615 1.0000 Uiso R . . . . . H31 H 0.6634 -0.0534 -0.3565 0.0390 1.0000 Uiso R . . . . . H61 H 0.0347 0.2633 -0.1504 0.0377 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 0.0646(13) 0.0342(9) 0.0377(10) -0.0024(7) 0.0175(9) -0.0087(8) O2 0.0672(13) 0.0287(9) 0.0407(10) -0.0040(7) 0.0146(9) -0.0067(8) N1 0.0351(10) 0.0278(9) 0.0305(9) -0.0069(7) 0.0017(8) -0.0062(7) C1 0.0467(15) 0.0316(12) 0.0439(14) -0.0104(10) 0.0081(11) -0.0029(10) C2 0.0330(11) 0.0299(11) 0.0347(12) -0.0088(9) 0.0015(9) -0.0039(9) C3 0.0355(12) 0.0350(12) 0.0304(11) -0.0097(9) 0.0020(9) -0.0061(9) C4 0.0345(11) 0.0285(11) 0.0270(10) -0.0038(8) 0.0002(8) -0.0072(8) C5 0.0414(13) 0.0312(11) 0.0301(11) -0.0046(9) 0.0033(9) -0.0085(9) C6 0.0357(12) 0.0265(10) 0.0302(11) -0.0056(8) -0.0002(9) -0.0060(9) C7 0.0328(11) 0.0236(10) 0.0286(11) -0.0055(8) -0.0011(8) -0.0044(8) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.871(19) 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 . C5 . 1.306(3) yes O1 . H1 . 0.861 no O2 . C5 . 1.234(3) yes N1 . C2 . 1.344(3) yes N1 . C7 . 1.346(3) yes C1 . C2 . 1.496(3) yes C1 . H11 . 0.952 no C1 . H12 . 0.967 no C1 . H13 . 0.973 no C2 . C3 . 1.396(3) yes C3 . C4 . 1.390(3) yes C3 . H31 . 0.980 no C4 . C5 . 1.489(3) yes C4 . C6 . 1.385(3) yes C6 . C7 . 1.398(3) yes C6 . H61 . 0.987 no C7 . C7 2_555 1.482(4) yes 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 C5 . O1 . H1 . 109.7 no C2 . N1 . C7 . 118.67(19) yes C2 . C1 . H11 . 110.7 no C2 . C1 . H12 . 108.8 no H11 . C1 . H12 . 106.3 no C2 . C1 . H13 . 111.9 no H11 . C1 . H13 . 110.0 no H12 . C1 . H13 . 109.0 no C1 . C2 . N1 . 116.5(2) yes C1 . C2 . C3 . 121.3(2) yes N1 . C2 . C3 . 122.2(2) yes C2 . C3 . C4 . 118.8(2) yes C2 . C3 . H31 . 120.9 no C4 . C3 . H31 . 120.3 no C3 . C4 . C5 . 121.7(2) yes C3 . C4 . C6 . 119.5(2) yes C5 . C4 . C6 . 118.8(2) yes C4 . C5 . O1 . 115.8(2) yes C4 . C5 . O2 . 121.2(2) yes O1 . C5 . O2 . 122.9(2) yes C4 . C6 . C7 . 118.3(2) yes C4 . C6 . H61 . 121.0 no C7 . C6 . H61 . 120.7 no C7 2_555 C7 . C6 . 120.8(2) yes C7 2_555 C7 . N1 . 116.5(2) yes C6 . C7 . N1 . 122.6(2) yes 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 O1 . H1 . O2 2_664 177 0.86 1.78 2.645(2) yes # Attachment '[Cu_3_2][PF6].cif' data_ah158_15 _database_code_depnum_ccdc_archive 'CCDC 717561' _audit_creation_date 08-04-02 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'ah158_15_173k_0m in P-1' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.9016(2) _cell_length_b 10.9570(3) _cell_length_c 19.0865(4) _cell_angle_alpha 81.7240(10) _cell_angle_beta 81.0490(10) _cell_angle_gamma 88.7430(10) _cell_volume 1819.78(8) _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' 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 0.0061 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' 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' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C44 H36 Cu1 F6 N4 O4 P1 # Dc = 1.63 Fooo = 860.00 Mu = 7.29 M = 893.30 # Found Formula = C40 H32 Cu1 F6 N4 O4 P1 # Dc = 1.54 FOOO = 860.00 Mu = 7.24 M = 841.23 _chemical_formula_sum 'C40 H32 Cu1 F6 N4 O4 P1' _chemical_formula_moiety 'C40 H32 Cu N4 O4, F6 P' _chemical_compound_source ? _chemical_formula_weight 841.23 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_min 0.03 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_max 0.26 _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 0.724 # Sheldrick geometric approximatio 0.92 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.98 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 173 _diffrn_reflns_number 61611 _reflns_number_total 13054 _diffrn_reflns_av_R_equivalents 0.051 # Number of reflections with Friedels Law is 13054 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 13155 _diffrn_reflns_theta_min 2.034 _diffrn_reflns_theta_max 32.510 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 31.535 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min -16 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.43 _refine_diff_density_max 0.43 _refine_ls_number_reflns 7298 _refine_ls_number_restraints 35 _refine_ls_number_parameters 505 #_refine_ls_R_factor_ref 0.0378 _refine_ls_wR_factor_ref 0.0408 _refine_ls_goodness_of_fit_ref 1.1057 #_reflns_number_all 13008 _refine_ls_R_factor_all 0.0715 _refine_ls_wR_factor_all 0.0594 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 7298 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_gt 0.0408 _refine_ls_shift/su_max 0.000568 # 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 F _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, 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: 1.04 1.14 0.975 0.346 0.197 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # 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 _atom_site_attached_hydrogens Cu1 Cu 0.58510(3) 0.14265(2) 0.269198(12) 0.0342 1.0000 Uani . . . . . . N1 N 0.43676(18) 0.01785(15) 0.32969(7) 0.0311 1.0000 Uani . . . . . . N2 N 0.57633(18) 0.20453(15) 0.36398(8) 0.0320 1.0000 Uani . . . . . . N3 N 0.76692(17) 0.11890(15) 0.19653(8) 0.0307 1.0000 Uani . . . . . . N4 N 0.50674(17) 0.23234(15) 0.18167(7) 0.0300 1.0000 Uani . . . . . . C1 C 0.4304(3) -0.0972(2) 0.23151(10) 0.0454 1.0000 Uani . . . . . . C2 C 0.3709(2) -0.07434(19) 0.30638(9) 0.0343 1.0000 Uani . . . . . . C3 C 0.2550(2) -0.14424(19) 0.34897(10) 0.0343 1.0000 Uani . . . . . . C4 C 0.2047(2) -0.11895(19) 0.41834(9) 0.0321 1.0000 Uani . . . . . . C5 C 0.2719(2) -0.02253(19) 0.44182(9) 0.0329 1.0000 Uani . . . . . . C6 C 0.3880(2) 0.04446(18) 0.39661(9) 0.0298 1.0000 Uani . . . . . . C7 C 0.4682(2) 0.14854(18) 0.41614(9) 0.0304 1.0000 Uani . . . . . . C8 C 0.4380(2) 0.18754(19) 0.48294(9) 0.0332 1.0000 Uani . . . . . . C9 C 0.5204(2) 0.28453(19) 0.49722(9) 0.0343 1.0000 Uani . . . . . . C10 C 0.6336(2) 0.3387(2) 0.44401(10) 0.0360 1.0000 Uani . . . . . . C11 C 0.6588(2) 0.29663(19) 0.37793(10) 0.0356 1.0000 Uani . . . . . . C12 C 0.7786(3) 0.3521(2) 0.31884(11) 0.0453 1.0000 Uani . . . . . . C13 C 0.8998(3) -0.0053(3) 0.28315(12) 0.0537 1.0000 Uani . . . . . . C14 C 0.8952(2) 0.0573(2) 0.20831(10) 0.0366 1.0000 Uani . . . . . . C15 C 1.0153(2) 0.0509(2) 0.15354(11) 0.0385 1.0000 Uani . . . . . . C16 C 1.0069(2) 0.11083(18) 0.08504(10) 0.0325 1.0000 Uani . . . . . . C17 C 0.8749(2) 0.17619(18) 0.07359(9) 0.0312 1.0000 Uani . . . . . . C18 C 0.75642(19) 0.17612(17) 0.12972(9) 0.0277 1.0000 Uani . . . . . . C19 C 0.60669(19) 0.23359(16) 0.12056(9) 0.0272 1.0000 Uani . . . . . . C20 C 0.5690(2) 0.28136(17) 0.05439(9) 0.0302 1.0000 Uani . . . . . . C21 C 0.4253(2) 0.33125(17) 0.05024(9) 0.0306 1.0000 Uani . . . . . . C22 C 0.3230(2) 0.32906(19) 0.11347(10) 0.0351 1.0000 Uani . . . . . . C23 C 0.3669(2) 0.27909(19) 0.17791(10) 0.0340 1.0000 Uani . . . . . . C24 C 0.2601(2) 0.2733(2) 0.24724(11) 0.0477 1.0000 Uani . . . . . . C25 C 0.0870(2) -0.1965(2) 0.46422(10) 0.0365 1.0000 Uani . . . . . . C26 C 0.0094(3) -0.2952(2) 0.45499(12) 0.0480 1.0000 Uani . . . . . . C27 C -0.0845(3) -0.3351(3) 0.52149(14) 0.0541 1.0000 Uani . . . . . . C28 C -0.0578(3) -0.2577(3) 0.56565(13) 0.0522 1.0000 Uani . . . . . . C29 C 0.4901(2) 0.3261(2) 0.56708(10) 0.0375 1.0000 Uani . . . . . . C30 C 0.3731(3) 0.3003(2) 0.62127(11) 0.0462 1.0000 Uani . . . . . . C31 C 0.4084(4) 0.3620(3) 0.67767(12) 0.0598 1.0000 Uani . . . . . . C32 C 0.5398(4) 0.4183(3) 0.65462(14) 0.0608 1.0000 Uani . . . . . . C33 C 1.1295(2) 0.1023(2) 0.02640(11) 0.0377 1.0000 Uani . . . . . . C35 C 1.3372(3) 0.0592(3) -0.04405(15) 0.0556 1.0000 Uani . . . . . . C36 C 1.2547(3) 0.1350(2) -0.08203(13) 0.0522 1.0000 Uani . . . . . . C37 C 0.3830(2) 0.38435(19) -0.01796(10) 0.0370 1.0000 Uani . U . . . . C39 C 0.3749(6) 0.4520(3) -0.13109(15) 0.0828 1.0000 Uani . U . . . . C40 C 0.2434(5) 0.4700(3) -0.0947(2) 0.0827 1.0000 Uani . U . . . . O1 O 0.04719(17) -0.17015(16) 0.53278(8) 0.0453 1.0000 Uani . . . . . . O2 O 0.5940(2) 0.39979(16) 0.58560(9) 0.0500 1.0000 Uani . . . . . . P1 P 0.92238(7) 0.36405(6) 0.79295(3) 0.0422 1.0000 Uani . . . . . . F1 F 0.9800(2) 0.49935(15) 0.79588(9) 0.0667 1.0000 Uani . . . . . . F2 F 0.8667(2) 0.22908(17) 0.78931(13) 0.0884 1.0000 Uani . . . . . . F3 F 0.8789(2) 0.34419(19) 0.87734(8) 0.0751 1.0000 Uani . . . . . . F4 F 0.9644(2) 0.3872(2) 0.70807(9) 0.0877 1.0000 Uani . . . . . . F5 F 0.75606(18) 0.41553(18) 0.78578(10) 0.0713 1.0000 Uani . . . . . . F6 F 1.08746(18) 0.31297(19) 0.79981(10) 0.0742 1.0000 Uani . . . . . . C54 C 1.2579(2) 0.0369(2) 0.02690(12) 0.0493 0.7500 Uani . . . . . . O3 O 1.1230(2) 0.16267(17) -0.03898(10) 0.0477 0.7500 Uani . . . . . . C58 C 0.4721(3) 0.3955(2) -0.08267(11) 0.0560 0.7000 Uani . U . . . . O4 O 0.2415(2) 0.42930(18) -0.02172(12) 0.0566 0.7000 Uani . U . . . . O30 O 1.2579(2) 0.0369(2) 0.02690(12) 0.0493 0.2500 Uani . . . . . . C134 C 1.1230(2) 0.16267(17) -0.03898(10) 0.0477 0.2500 Uani . . . . . . O40 O 0.4721(3) 0.3955(2) -0.08267(11) 0.0560 0.3000 Uani . . . . . . C138 C 0.2415(2) 0.42930(18) -0.02172(12) 0.0566 0.3000 Uani . . . . . . H11 H 0.3956 -0.1736 0.2213 0.0676 1.0000 Uiso R . . . . . H12 H 0.5391 -0.0994 0.2248 0.0680 1.0000 Uiso R . . . . . H13 H 0.4001 -0.0316 0.1976 0.0679 1.0000 Uiso R . . . . . H31 H 0.2094 -0.2084 0.3327 0.0421 1.0000 Uiso R . . . . . H51 H 0.2413 -0.0017 0.4874 0.0383 1.0000 Uiso R . . . . . H81 H 0.3613 0.1494 0.5172 0.0395 1.0000 Uiso R . . . . . H101 H 0.6931 0.4051 0.4522 0.0450 1.0000 Uiso R . . . . . H121 H 0.8254 0.4196 0.3338 0.0679 1.0000 Uiso R . . . . . H122 H 0.8535 0.2899 0.3088 0.0684 1.0000 Uiso R . . . . . H123 H 0.7339 0.3811 0.2771 0.0680 1.0000 Uiso R . . . . . H131 H 0.9818 -0.0591 0.2864 0.0807 1.0000 Uiso R . . . . . H132 H 0.9071 0.0547 0.3140 0.0805 1.0000 Uiso R . . . . . H133 H 0.8102 -0.0501 0.3005 0.0806 1.0000 Uiso R . . . . . H151 H 1.1034 0.0065 0.1622 0.0465 1.0000 Uiso R . . . . . H171 H 0.8662 0.2202 0.0273 0.0381 1.0000 Uiso R . . . . . H201 H 0.6433 0.2797 0.0118 0.0373 1.0000 Uiso R . . . . . H221 H 0.2260 0.3620 0.1126 0.0433 1.0000 Uiso R . . . . . H241 H 0.1722 0.3210 0.2398 0.0702 1.0000 Uiso R . . . . . H242 H 0.3080 0.3050 0.2836 0.0706 1.0000 Uiso R . . . . . H243 H 0.2287 0.1899 0.2648 0.0702 1.0000 Uiso R . . . . . H261 H 0.0165 -0.3308 0.4117 0.0576 1.0000 Uiso R . . . . . H271 H -0.1528 -0.4040 0.5338 0.0637 1.0000 Uiso R . . . . . H281 H -0.1018 -0.2603 0.6142 0.0611 1.0000 Uiso R . . . . . H301 H 0.2885 0.2518 0.6225 0.0566 1.0000 Uiso R . . . . . H311 H 0.3480 0.3623 0.7223 0.0725 1.0000 Uiso R . . . . . H321 H 0.5934 0.4654 0.6800 0.0773 1.0000 Uiso R . . . . . H341 H 1.2849 -0.0102 0.0639 0.0517 0.7500 Uiso . . . . . . H351 H 1.4306 0.0268 -0.0611 0.0679 1.0000 Uiso R . . . . . H361 H 1.2791 0.1667 -0.1309 0.0631 1.0000 Uiso R . . . . . H391 H 0.3997 0.4720 -0.1797 0.1005 1.0000 Uiso R . . . . . H401 H 0.1607 0.5056 -0.1131 0.1096 1.0000 Uiso R . . . . . H381 H 0.5755 0.3711 -0.0933 0.0556 0.7000 Uiso . . . . . . H1341 H 1.0418 0.2153 -0.0531 0.0572 0.2500 Uiso . . . . . . H1381 H 0.1582 0.4327 0.0171 0.0721 0.3000 Uiso . . . . . . 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 Cu1 0.03480(12) 0.04433(14) 0.01970(9) 0.00120(8) 0.00176(8) 0.00563(10) N1 0.0322(7) 0.0380(8) 0.0208(6) 0.0002(6) -0.0019(5) 0.0066(6) N2 0.0327(7) 0.0384(9) 0.0228(6) -0.0003(6) -0.0019(5) 0.0055(6) N3 0.0306(7) 0.0347(8) 0.0252(6) -0.0024(6) -0.0019(5) 0.0048(6) N4 0.0298(7) 0.0341(8) 0.0230(6) -0.0001(6) 0.0012(5) 0.0045(6) C1 0.0495(12) 0.0586(14) 0.0259(8) -0.0107(9) 0.0060(8) -0.0076(10) C2 0.0349(9) 0.0439(11) 0.0218(7) -0.0009(7) -0.0013(6) 0.0071(8) C3 0.0322(9) 0.0424(11) 0.0270(8) -0.0035(7) -0.0024(7) 0.0022(8) C4 0.0262(8) 0.0419(10) 0.0251(7) 0.0017(7) -0.0013(6) 0.0070(7) C5 0.0324(8) 0.0425(10) 0.0216(7) -0.0019(7) -0.0013(6) 0.0090(8) C6 0.0302(8) 0.0359(9) 0.0211(7) 0.0006(6) -0.0032(6) 0.0091(7) C7 0.0306(8) 0.0371(10) 0.0215(7) 0.0007(6) -0.0033(6) 0.0096(7) C8 0.0347(9) 0.0411(10) 0.0216(7) -0.0003(7) -0.0029(6) 0.0071(8) C9 0.0389(9) 0.0389(10) 0.0244(8) -0.0022(7) -0.0070(7) 0.0115(8) C10 0.0393(10) 0.0373(10) 0.0313(9) -0.0043(7) -0.0061(7) 0.0035(8) C11 0.0363(9) 0.0405(11) 0.0272(8) 0.0008(7) -0.0026(7) 0.0057(8) C12 0.0457(11) 0.0504(13) 0.0353(10) -0.0029(9) 0.0061(8) -0.0070(10) C13 0.0463(12) 0.0735(17) 0.0363(10) 0.0079(10) -0.0078(9) 0.0204(12) C14 0.0344(9) 0.0415(11) 0.0320(9) -0.0013(8) -0.0035(7) 0.0070(8) C15 0.0287(9) 0.0454(11) 0.0402(10) -0.0062(8) -0.0028(7) 0.0085(8) C16 0.0281(8) 0.0352(10) 0.0336(9) -0.0097(7) 0.0021(7) -0.0018(7) C17 0.0312(8) 0.0358(9) 0.0246(7) -0.0041(7) 0.0018(6) -0.0003(7) C18 0.0285(8) 0.0297(9) 0.0237(7) -0.0033(6) -0.0011(6) 0.0019(7) C19 0.0283(8) 0.0293(8) 0.0223(7) -0.0018(6) -0.0005(6) 0.0013(6) C20 0.0346(9) 0.0331(9) 0.0221(7) -0.0036(6) -0.0022(6) -0.0013(7) C21 0.0371(9) 0.0280(9) 0.0275(8) -0.0015(6) -0.0097(7) -0.0029(7) C22 0.0295(8) 0.0375(10) 0.0362(9) 0.0012(8) -0.0053(7) 0.0030(7) C23 0.0302(8) 0.0374(10) 0.0305(8) 0.0018(7) 0.0006(7) 0.0042(7) C24 0.0365(10) 0.0598(14) 0.0367(10) 0.0081(9) 0.0095(8) 0.0163(10) C25 0.0303(9) 0.0477(12) 0.0280(8) 0.0002(8) -0.0002(7) 0.0066(8) C26 0.0415(11) 0.0618(15) 0.0383(10) -0.0034(10) -0.0007(9) -0.0061(10) C27 0.0402(12) 0.0631(16) 0.0511(13) 0.0069(12) 0.0049(10) -0.0069(11) C28 0.0389(11) 0.0690(16) 0.0388(11) 0.0065(11) 0.0115(9) 0.0013(11) C29 0.0450(11) 0.0413(11) 0.0263(8) -0.0047(7) -0.0069(7) 0.0102(9) C30 0.0489(12) 0.0541(14) 0.0333(10) -0.0034(9) -0.0028(9) 0.0030(10) C31 0.0822(19) 0.0644(17) 0.0305(10) -0.0098(10) -0.0011(11) 0.0188(15) C32 0.089(2) 0.0593(16) 0.0425(12) -0.0213(11) -0.0247(13) 0.0144(15) C33 0.0300(9) 0.0435(11) 0.0393(10) -0.0147(8) 0.0046(7) -0.0045(8) C35 0.0313(10) 0.0686(17) 0.0667(16) -0.0284(13) 0.0109(10) -0.0009(11) C36 0.0612(15) 0.0483(13) 0.0428(12) -0.0139(10) 0.0137(10) -0.0114(11) C37 0.0479(11) 0.0340(10) 0.0319(8) -0.0009(7) -0.0179(8) -0.0055(8) C39 0.166(3) 0.0539(16) 0.0355(12) 0.0012(11) -0.0402(16) -0.027(2) C40 0.131(3) 0.0490(15) 0.089(2) -0.0005(15) -0.0891(19) -0.0016(18) O1 0.0397(8) 0.0596(10) 0.0314(7) -0.0028(6) 0.0072(6) 0.0034(7) O2 0.0594(10) 0.0516(10) 0.0420(8) -0.0123(7) -0.0128(7) 0.0063(8) P1 0.0404(3) 0.0520(3) 0.0355(3) -0.0059(2) -0.0093(2) -0.0030(2) F1 0.0704(10) 0.0587(10) 0.0739(11) -0.0060(8) -0.0223(8) -0.0089(8) F2 0.0951(14) 0.0579(11) 0.1204(17) -0.0134(11) -0.0395(13) -0.0149(10) F3 0.0727(11) 0.1090(15) 0.0380(7) 0.0050(8) -0.0063(7) 0.0037(10) F4 0.0949(14) 0.1332(18) 0.0360(8) -0.0176(9) -0.0057(8) -0.0176(13) F5 0.0469(8) 0.0917(13) 0.0746(11) 0.0030(9) -0.0218(8) 0.0049(8) F6 0.0492(9) 0.0946(13) 0.0839(12) -0.0267(10) -0.0161(8) 0.0190(9) C54 0.0346(9) 0.0666(14) 0.0460(11) -0.0082(10) -0.0046(8) 0.0063(9) O3 0.0484(9) 0.0440(9) 0.0480(9) -0.0083(7) 0.0020(7) 0.0035(7) C58 0.0804(16) 0.0476(12) 0.0401(10) -0.0093(9) -0.0042(10) -0.0155(11) O4 0.0590(11) 0.0499(11) 0.0687(12) -0.0054(9) -0.0372(10) 0.0015(9) O30 0.0346(9) 0.0666(14) 0.0460(11) -0.0082(10) -0.0046(8) 0.0063(9) C134 0.0484(9) 0.0440(9) 0.0480(9) -0.0083(7) 0.0020(7) 0.0035(7) O40 0.0804(16) 0.0476(12) 0.0401(10) -0.0093(9) -0.0042(10) -0.0155(11) C138 0.0590(11) 0.0499(11) 0.0687(12) -0.0054(9) -0.0372(10) 0.0015(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4059(4) 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 Cu1 . N1 . 2.0241(16) yes Cu1 . N2 . 2.0113(16) yes Cu1 . N3 . 1.9995(15) yes Cu1 . N4 . 2.0257(15) yes N1 . C2 . 1.341(3) yes N1 . C6 . 1.354(2) yes N2 . C7 . 1.359(2) yes N2 . C11 . 1.341(3) yes N3 . C14 . 1.347(2) yes N3 . C18 . 1.354(2) yes N4 . C19 . 1.351(2) yes N4 . C23 . 1.344(2) yes C1 . C2 . 1.499(3) yes C1 . H11 . 0.955 no C1 . H12 . 0.957 no C1 . H13 . 0.959 no C2 . C3 . 1.381(3) yes C3 . C4 . 1.395(3) yes C3 . H31 . 0.932 no C4 . C5 . 1.386(3) yes C4 . C25 . 1.458(3) yes C5 . C6 . 1.387(3) yes C5 . H51 . 0.930 no C6 . C7 . 1.480(3) yes C7 . C8 . 1.388(2) yes C8 . C9 . 1.386(3) yes C8 . H81 . 0.929 no C9 . C10 . 1.391(3) yes C9 . C29 . 1.454(3) yes C10 . C11 . 1.389(3) yes C10 . H101 . 0.953 no C11 . C12 . 1.496(3) yes C12 . H121 . 0.956 no C12 . H122 . 0.961 no C12 . H123 . 0.956 no C13 . C14 . 1.499(3) yes C13 . H131 . 0.932 no C13 . H132 . 0.953 no C13 . H133 . 0.936 no C14 . C15 . 1.382(3) yes C15 . C16 . 1.388(3) yes C15 . H151 . 0.938 no C16 . C17 . 1.393(3) yes C16 . C33 . 1.448(2) yes C17 . C18 . 1.381(2) yes C17 . H171 . 0.957 no C18 . C19 . 1.486(2) yes C19 . C20 . 1.384(2) yes C20 . C21 . 1.390(3) yes C20 . H201 . 0.967 no C21 . C22 . 1.392(3) yes C21 . C37 . 1.449(2) yes C22 . C23 . 1.383(3) yes C22 . H221 . 0.930 no C23 . C24 . 1.499(3) yes C24 . H241 . 0.949 no C24 . H242 . 0.976 no C24 . H243 . 0.959 no C25 . C26 . 1.342(3) yes C25 . O1 . 1.372(2) yes C26 . C27 . 1.424(3) yes C26 . H261 . 0.956 no C27 . C28 . 1.328(4) yes C27 . H271 . 0.959 no C28 . O1 . 1.368(3) yes C28 . H281 . 0.944 no C29 . C30 . 1.352(3) yes C29 . O2 . 1.360(3) yes C30 . C31 . 1.428(4) yes C30 . H301 . 0.927 no C31 . C32 . 1.318(4) yes C31 . H311 . 0.935 no C32 . O2 . 1.372(3) yes C32 . H321 . 0.940 no C33 . C54 . 1.337(3) yes C33 . O3 . 1.334(3) yes C33 . O30 . 1.337(3) yes C33 . C134 . 1.334(3) yes C35 . C36 . 1.311(4) yes C35 . C54 . 1.416(3) yes C35 . O30 . 1.416(3) yes C35 . H351 . 0.928 no C36 . O3 . 1.378(3) yes C36 . C134 . 1.378(3) yes C36 . H361 . 0.941 no C37 . C58 . 1.351(3) yes C37 . O4 . 1.351(3) yes C37 . O40 . 1.351(3) yes C37 . C138 . 1.351(3) yes C39 . C40 . 1.291(5) yes C39 . C58 . 1.431(4) yes C39 . O40 . 1.431(4) yes C39 . H391 . 0.916 no C40 . O4 . 1.397(4) yes C40 . C138 . 1.397(4) yes C40 . H401 . 0.920 no P1 . F1 . 1.5907(18) yes P1 . F2 . 1.5843(19) yes P1 . F3 . 1.5812(16) yes P1 . F4 . 1.5894(17) yes P1 . F5 . 1.5915(16) yes P1 . F6 . 1.5787(17) yes C54 . H341 . 0.875 no O3 . H1341 . 0.963 no C58 . H381 . 0.952 no O4 . H1381 . 0.967 no O30 . H341 . 0.875 no C134 . H1341 . 0.963 no O40 . H381 . 0.952 no C138 . H1381 . 0.967 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 N1 . Cu1 . N2 . 81.27(7) yes N1 . Cu1 . N3 . 130.31(7) yes N2 . Cu1 . N3 . 128.77(7) yes N1 . Cu1 . N4 . 113.72(6) yes N2 . Cu1 . N4 . 126.03(6) yes N3 . Cu1 . N4 . 81.94(6) yes Cu1 . N1 . C2 . 125.98(12) yes Cu1 . N1 . C6 . 113.90(13) yes C2 . N1 . C6 . 119.45(16) yes Cu1 . N2 . C7 . 113.76(13) yes Cu1 . N2 . C11 . 126.65(12) yes C7 . N2 . C11 . 119.49(16) yes Cu1 . N3 . C14 . 126.95(12) yes Cu1 . N3 . C18 . 113.95(12) yes C14 . N3 . C18 . 119.06(15) yes Cu1 . N4 . C19 . 113.41(11) yes Cu1 . N4 . C23 . 127.43(12) yes C19 . N4 . C23 . 118.90(15) yes C2 . C1 . H11 . 112.5 no C2 . C1 . H12 . 109.5 no H11 . C1 . H12 . 107.8 no C2 . C1 . H13 . 110.1 no H11 . C1 . H13 . 108.8 no H12 . C1 . H13 . 108.0 no C1 . C2 . N1 . 116.17(17) yes C1 . C2 . C3 . 121.9(2) yes N1 . C2 . C3 . 121.88(17) yes C2 . C3 . C4 . 119.36(19) yes C2 . C3 . H31 . 121.8 no C4 . C3 . H31 . 118.8 no C3 . C4 . C5 . 118.50(17) yes C3 . C4 . C25 . 119.15(19) yes C5 . C4 . C25 . 122.33(17) yes C4 . C5 . C6 . 119.54(16) yes C4 . C5 . H51 . 121.5 no C6 . C5 . H51 . 118.9 no C5 . C6 . N1 . 121.25(18) yes C5 . C6 . C7 . 124.15(16) yes N1 . C6 . C7 . 114.60(16) yes C6 . C7 . N2 . 115.46(15) yes C6 . C7 . C8 . 123.34(17) yes N2 . C7 . C8 . 121.19(19) yes C7 . C8 . C9 . 119.63(18) yes C7 . C8 . H81 . 119.6 no C9 . C8 . H81 . 120.8 no C8 . C9 . C10 . 118.56(17) yes C8 . C9 . C29 . 120.17(18) yes C10 . C9 . C29 . 121.3(2) yes C9 . C10 . C11 . 119.5(2) yes C9 . C10 . H101 . 120.8 no C11 . C10 . H101 . 119.7 no C10 . C11 . N2 . 121.58(18) yes C10 . C11 . C12 . 121.6(2) yes N2 . C11 . C12 . 116.82(18) yes C11 . C12 . H121 . 109.4 no C11 . C12 . H122 . 108.3 no H121 . C12 . H122 . 109.5 no C11 . C12 . H123 . 109.8 no H121 . C12 . H123 . 109.4 no H122 . C12 . H123 . 110.4 no C14 . C13 . H131 . 113.0 no C14 . C13 . H132 . 110.0 no H131 . C13 . H132 . 107.7 no C14 . C13 . H133 . 110.0 no H131 . C13 . H133 . 108.2 no H132 . C13 . H133 . 107.7 no C13 . C14 . N3 . 116.70(17) yes C13 . C14 . C15 . 122.02(18) yes N3 . C14 . C15 . 121.27(18) yes C14 . C15 . C16 . 120.22(18) yes C14 . C15 . H151 . 120.6 no C16 . C15 . H151 . 119.2 no C15 . C16 . C17 . 118.13(16) yes C15 . C16 . C33 . 121.13(18) yes C17 . C16 . C33 . 120.70(18) yes C16 . C17 . C18 . 119.21(17) yes C16 . C17 . H171 . 120.3 no C18 . C17 . H171 . 120.4 no C17 . C18 . N3 . 122.04(16) yes C17 . C18 . C19 . 122.64(15) yes N3 . C18 . C19 . 115.27(14) yes C18 . C19 . N4 . 115.05(14) yes C18 . C19 . C20 . 123.04(15) yes N4 . C19 . C20 . 121.88(16) yes C19 . C20 . C21 . 119.49(16) yes C19 . C20 . H201 . 119.4 no C21 . C20 . H201 . 121.1 no C20 . C21 . C22 . 118.16(16) yes C20 . C21 . C37 . 120.99(17) yes C22 . C21 . C37 . 120.86(18) yes C21 . C22 . C23 . 119.65(17) yes C21 . C22 . H221 . 120.4 no C23 . C22 . H221 . 120.0 no C22 . C23 . N4 . 121.91(17) yes C22 . C23 . C24 . 121.54(17) yes N4 . C23 . C24 . 116.55(17) yes C23 . C24 . H241 . 109.4 no C23 . C24 . H242 . 111.1 no H241 . C24 . H242 . 109.0 no C23 . C24 . H243 . 110.5 no H241 . C24 . H243 . 108.3 no H242 . C24 . H243 . 108.5 no C4 . C25 . C26 . 133.43(19) yes C4 . C25 . O1 . 116.28(19) yes C26 . C25 . O1 . 110.23(18) yes C25 . C26 . C27 . 106.8(2) yes C25 . C26 . H261 . 126.0 no C27 . C26 . H261 . 127.2 no C26 . C27 . C28 . 106.0(2) yes C26 . C27 . H271 . 128.6 no C28 . C27 . H271 . 125.3 no C27 . C28 . O1 . 111.6(2) yes C27 . C28 . H281 . 126.6 no O1 . C28 . H281 . 121.8 no C9 . C29 . C30 . 130.5(2) yes C9 . C29 . O2 . 118.68(19) yes C30 . C29 . O2 . 110.79(19) yes C29 . C30 . C31 . 105.3(2) yes C29 . C30 . H301 . 127.9 no C31 . C30 . H301 . 126.7 no C30 . C31 . C32 . 107.3(2) yes C30 . C31 . H311 . 125.7 no C32 . C31 . H311 . 127.0 no C31 . C32 . O2 . 110.8(2) yes C31 . C32 . H321 . 127.2 no O2 . C32 . H321 . 122.0 no C16 . C33 . C54 . 128.4(2) yes C16 . C33 . O3 . 121.05(19) yes C54 . C33 . O3 . 110.56(18) yes C16 . C33 . O30 . 128.4(2) yes O3 . C33 . O30 . 110.56(18) yes C16 . C33 . C134 . 121.05(19) yes C54 . C33 . C134 . 110.56(18) yes O30 . C33 . C134 . 110.56(18) yes C36 . C35 . C54 . 107.7(2) yes C36 . C35 . O30 . 107.7(2) yes C36 . C35 . H351 . 125.5 no C54 . C35 . H351 . 126.8 no O30 . C35 . H351 . 126.8 no C35 . C36 . O3 . 109.3(2) yes C35 . C36 . C134 . 109.3(2) yes C35 . C36 . H361 . 126.8 no O3 . C36 . H361 . 124.0 no C134 . C36 . H361 . 124.0 no C21 . C37 . C58 . 126.9(2) yes C21 . C37 . O4 . 120.5(2) yes C58 . C37 . O4 . 112.6(2) yes C21 . C37 . O40 . 126.9(2) yes O4 . C37 . O40 . 112.6(2) yes C21 . C37 . C138 . 120.5(2) yes C58 . C37 . C138 . 112.6(2) yes O40 . C37 . C138 . 112.6(2) yes C40 . C39 . C58 . 108.4(3) yes C40 . C39 . O40 . 108.4(3) yes C40 . C39 . H391 . 124.9 no C58 . C39 . H391 . 126.7 no O40 . C39 . H391 . 126.7 no C39 . C40 . O4 . 111.1(3) yes C39 . C40 . C138 . 111.1(3) yes C39 . C40 . H401 . 125.7 no O4 . C40 . H401 . 123.1 no C138 . C40 . H401 . 123.1 no C25 . O1 . C28 . 105.34(19) yes C32 . O2 . C29 . 105.7(2) yes F1 . P1 . F2 . 179.32(12) yes F1 . P1 . F3 . 89.52(10) yes F2 . P1 . F3 . 91.00(12) yes F1 . P1 . F4 . 89.50(11) yes F2 . P1 . F4 . 89.99(12) yes F3 . P1 . F4 . 178.65(12) yes F1 . P1 . F5 . 90.47(10) yes F2 . P1 . F5 . 89.97(11) yes F3 . P1 . F5 . 89.90(10) yes F4 . P1 . F5 . 89.19(11) yes F1 . P1 . F6 . 89.56(10) yes F2 . P1 . F6 . 90.00(11) yes F3 . P1 . F6 . 90.27(10) yes F4 . P1 . F6 . 90.65(11) yes F5 . P1 . F6 . 179.83(10) yes C35 . C54 . C33 . 105.7(2) yes C35 . C54 . H341 . 128.3 no C33 . C54 . H341 . 126.0 no C36 . O3 . C33 . 106.78(19) yes C36 . O3 . H1341 . 126.8 no C33 . O3 . H1341 . 126.4 no C39 . C58 . C37 . 103.9(3) yes C39 . C58 . H381 . 128.4 no C37 . C58 . H381 . 127.7 no C40 . O4 . C37 . 104.0(3) yes C40 . O4 . H1381 . 128.0 no C37 . O4 . H1381 . 128.0 no C35 . O30 . C33 . 105.7(2) yes C35 . O30 . H341 . 128.3 no C33 . O30 . H341 . 126.0 no C36 . C134 . C33 . 106.78(19) yes C36 . C134 . H1341 . 126.8 no C33 . C134 . H1341 . 126.4 no C39 . O40 . C37 . 103.9(3) yes C39 . O40 . H381 . 128.4 no C37 . O40 . H381 . 127.7 no C40 . C138 . C37 . 104.0(3) yes C40 . C138 . H1381 . 128.0 no C37 . C138 . H1381 . 128.0 no # Attachment '[Cu_H22__H2_].cif' data_ah099_173k _database_code_depnum_ccdc_archive 'CCDC 717562' _audit_creation_date 08-12-19 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title '10171521 ah099_173k' _chemical_name_systematic ? _chemical_melting_point ? _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_related_literature # Not in version 2.3.1 ############################################################### # Essential references (e.g. to the origin of the material studied, related # structural studies, and to information supporting the reported structure) # should be cited in this section, with appropriate very brief explanatory # text, for example `The synthesis of the complex is described by Jones # (2001). The anhydrous complex has essentially the same coordination # geometry (Smith, 2003).' In addition, all references included in the # supplementary materials, but not elsewhere in the published article, # should be given here. The simple text `For related literature, see:...' # may be used, but further details should be provided in the Comment # section, which forms part of the supplementary material. ############################################################### ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fig. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; # data_1 _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 19.3405(4) _cell_length_b 19.6142(4) _cell_length_c 15.5801(3) _cell_angle_alpha 90 _cell_angle_beta 114.0211(9) _cell_angle_gamma 90 _cell_volume 5398.43(19) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 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' 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' 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' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C112 H96 Cl4 Cu4 N16 O32 # Dc = 1.58 Fooo = 2556.00 Mu = 9.68 M = 643.52 # Found Formula = C112 H98 Cu4 N16 O35 # Dc = 1.53 FOOO = 2556.00 Mu = 8.71 M = 620.57 _chemical_formula_sum 'C112 H98 Cu4 N16 O35' _chemical_formula_moiety '4(C28 H23 Cu N4 O8), 3(H2 O)' _chemical_compound_source ? _chemical_formula_weight 2482.28 _cell_measurement_reflns_used 23026 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_max 0.37 _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2556 _exptl_absorpt_coefficient_mu 0.871 # Sheldrick geometric approximatio 0.86 0.92 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.92 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 173 _diffrn_reflns_number 45813 _reflns_number_total 6190 _diffrn_reflns_av_R_equivalents 0.033 # Number of reflections with Friedels Law is 6190 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 6188 _diffrn_reflns_theta_min 1.764 _diffrn_reflns_theta_max 27.479 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.479 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _reflns_limit_h_min -25 _reflns_limit_h_max 22 _reflns_limit_k_min 0 _reflns_limit_k_max 25 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.36 _refine_diff_density_max 0.49 # 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>3.0\s(I) _refine_ls_number_reflns 4532 _refine_ls_number_restraints 313 _refine_ls_number_parameters 449 _oxford_refine_ls_R_factor_ref 0.0341 _refine_ls_wR_factor_ref 0.0357 _refine_ls_goodness_of_fit_ref 1.0436 _refine_ls_shift/su_max 0.024773 # The values computed from all data _oxford_reflns_number_all 6126 _refine_ls_R_factor_all 0.0468 _refine_ls_wR_factor_all 0.0394 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4865 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_gt 0.0364 # 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 F _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, 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: 0.962 0.176 0.672 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # 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 Cu1 Cu 0.728933(12) 0.530835(11) 0.762241(14) 0.0287 1.0000 Uani . . . . . . . N1 N 0.80723(9) 0.47887(7) 0.87441(10) 0.0295 1.0000 Uani . . . . . . . N2 N 0.72372(8) 0.58872(7) 0.86857(10) 0.0277 1.0000 Uani . . . . . . . N3 N 0.64896(8) 0.49254(7) 0.64103(10) 0.0275 1.0000 Uani . . . . . . . N4 N 0.75867(9) 0.58243(8) 0.66779(10) 0.0327 1.0000 Uani . . . . . . . C1 C 0.84561(12) 0.42192(10) 0.87216(13) 0.0356 1.0000 Uani . . . . . . . C2 C 0.91053(12) 0.40300(10) 0.95020(14) 0.0383 1.0000 Uani . . . . . . . C3 C 0.93650(13) 0.44437(12) 1.02900(16) 0.0496 1.0000 Uani . . . . . . . C4 C 0.89494(12) 0.50105(11) 1.03235(15) 0.0459 1.0000 Uani . . . . . . . C5 C 0.82902(10) 0.51560(9) 0.95451(12) 0.0301 1.0000 Uani . . . . . . . C6 C 0.77806(10) 0.57271(8) 0.95332(12) 0.0283 1.0000 Uani . . . . . . . C7 C 0.78475(11) 0.60603(10) 1.03478(13) 0.0365 1.0000 Uani . . . . . . . C8 C 0.73418(11) 0.65765(10) 1.02795(13) 0.0369 1.0000 Uani . . . . . . . C9 C 0.67940(10) 0.67649(9) 0.94064(13) 0.0323 1.0000 Uani . . . . . . . C10 C 0.67525(10) 0.64027(9) 0.86052(12) 0.0312 1.0000 Uani . . . . . . . C11 C 0.95431(13) 0.33800(11) 0.95555(14) 0.0447 1.0000 Uani . . . . . . . C12 C 0.81441(16) 0.38149(13) 0.78264(16) 0.0557 1.0000 Uani . . . . . . . C13 C 0.61843(13) 0.65481(13) 0.76273(15) 0.0501 1.0000 Uani . . . . . . . C14 C 0.62640(11) 0.73386(11) 0.93420(15) 0.0406 1.0000 Uani . . . . . . . C15 C 0.59947(11) 0.44186(10) 0.63410(13) 0.0354 1.0000 Uani . U . . . . . C16 C 0.55390(11) 0.41363(10) 0.54643(13) 0.0358 1.0000 Uani . U . . . . . C17 C 0.55820(11) 0.44017(10) 0.46659(13) 0.0355 1.0000 Uani . U . . . . . C18 C 0.60741(11) 0.49341(10) 0.47369(13) 0.0336 1.0000 Uani . . . . . . . C19 C 0.65311(9) 0.51761(8) 0.56283(12) 0.0268 1.0000 Uani . . . . . . . C20 C 0.71069(10) 0.57170(9) 0.57772(12) 0.0279 1.0000 Uani . . . . . . . C21 C 0.71532(13) 0.60851(12) 0.50472(14) 0.0443 1.0000 Uani . . . . . . . C22 C 0.77202(13) 0.65660(11) 0.52492(14) 0.0438 1.0000 Uani . U . . . . . C23 C 0.82164(12) 0.66731(11) 0.61669(14) 0.0416 1.0000 Uani . U . . . . . C24 C 0.81320(13) 0.62988(12) 0.68805(14) 0.0479 1.0000 Uani . U . . . . . C25 C 0.59809(17) 0.41958(16) 0.72566(16) 0.0663 1.0000 Uani . . . . . . . C26 C 0.4948(10) 0.3577(11) 0.5345(13) 0.0514 0.5000 Uani . U . . . . . C27 C 0.8720(3) 0.7303(3) 0.6379(4) 0.0439 0.5000 Uani . U . . . . . C28 C 0.8584(3) 0.6468(3) 0.7907(3) 0.0633 0.7500 Uani . U . . . . . C36 C 0.5065(10) 0.3513(10) 0.5348(13) 0.0510 0.5000 Uani . U . . . . . C37 C 0.8927(4) 0.7100(3) 0.6340(4) 0.0471 0.5000 Uani . U . . . . . C38 C 0.8778(10) 0.6193(8) 0.7853(11) 0.0650 0.2500 Uani . U . . . . . O1 O 0.62510(9) 0.74905(8) 1.01545(11) 0.0479 1.0000 Uani . . . . . . . O2 O 0.59085(11) 0.76425(10) 0.86186(12) 0.0656 1.0000 Uani . . . . . . . O3 O 0.91341(11) 0.28585(8) 0.92064(14) 0.0667 1.0000 Uani . . . . . . . O4 O 1.02368(10) 0.34029(9) 0.99527(12) 0.0552 1.0000 Uani . . . . . . . O5 O 0.4819(7) 0.3270(7) 0.4549(10) 0.0452 0.5000 Uani . U . . . . . O6 O 0.4709(2) 0.3523(2) 0.5956(3) 0.0602 0.5000 Uani . U . . . . . O7 O 0.9228(2) 0.7188(2) 0.6043(3) 0.0645 0.5000 Uani . U . . . . . O8 O 0.8653(2) 0.78074(17) 0.6765(3) 0.0610 0.5000 Uani . U . . . . . O9 O 0.500000(10) 0.87270(15) 0.750000(10) 0.0851 1.0000 Uani S T . . . . . O10 O 0.4389(7) 0.9914(6) 0.7601(6) 0.1013 0.2500 Uani . . . . . . . O50 O 0.4665(7) 0.3279(8) 0.4558(10) 0.0498 0.5000 Uani . U . . . . . O60 O 0.5069(3) 0.3197(2) 0.6073(3) 0.0710 0.5000 Uani . U . . . . . O70 O 0.9572(2) 0.6899(2) 0.6706(3) 0.0651 0.5000 Uani . U . . . . . O80 O 0.8720(2) 0.7705(2) 0.6031(3) 0.0654 0.5000 Uani . U . . . . . H1 H 0.5875 0.7714 1.0030 0.0712 1.0000 Uiso R . . . . . . H2 H 0.9337 0.2483 0.9238 0.0702 1.0000 Uiso R . . . . . . H4 H 0.5187 0.8457 0.7930 0.1151 1.0000 Uiso R . . . . . . H6 H 0.4417 0.9497 0.7597 0.1192 0.2500 Uiso R . . . . . . H31 H 0.9815 0.4327 1.0802 0.0544 1.0000 Uiso R . . . . . . H41 H 0.9115 0.5292 1.0855 0.0499 1.0000 Uiso R . . . . . . H71 H 0.8224 0.5945 1.0914 0.0410 1.0000 Uiso R . . . . . . H81 H 0.7377 0.6807 1.0828 0.0433 1.0000 Uiso R . . . . . . H121 H 0.8561 0.3627 0.7690 0.0785 1.0000 Uiso R . . . . . . H122 H 0.7827 0.4112 0.7318 0.0783 1.0000 Uiso R . . . . . . H123 H 0.7839 0.3436 0.7918 0.0801 1.0000 Uiso R . . . . . . H131 H 0.6167 0.6181 0.7215 0.0696 1.0000 Uiso R . . . . . . H132 H 0.5699 0.6626 0.7626 0.0694 1.0000 Uiso R . . . . . . H133 H 0.6337 0.6958 0.7425 0.0700 1.0000 Uiso R . . . . . . H171 H 0.5280 0.4220 0.4068 0.0417 1.0000 Uiso R . . . . . . H181 H 0.6094 0.5118 0.4210 0.0403 1.0000 Uiso R . . . . . . H211 H 0.6805 0.6015 0.4432 0.0517 1.0000 Uiso R . . . . . . H231 H 0.7763 0.6828 0.4758 0.0537 1.0000 Uiso R . . . . . . H251 H 0.6075 0.3715 0.7348 0.1003 1.0000 Uiso R . . . . . . H252 H 0.6369 0.4445 0.7771 0.0997 1.0000 Uiso R . . . . . . H253 H 0.5493 0.4288 0.7279 0.1005 1.0000 Uiso R . . . . . . H281 H 0.8800 0.6053 0.8212 0.0828 0.7500 Uiso R . . . . . . H282 H 0.8239 0.6648 0.8142 0.0828 0.7500 Uiso R . . . . . . H283 H 0.8975 0.6785 0.7980 0.0828 0.7500 Uiso R . . . . . . H381 H 0.9180 0.6494 0.7918 0.0847 0.2500 Uiso R . . . . . . H382 H 0.8980 0.5768 0.8137 0.0847 0.2500 Uiso R . . . . . . H383 H 0.8531 0.6383 0.8214 0.0847 0.2500 Uiso R . . . . . . H5 H 0.4759 1.0080 0.7548 0.1192 0.2500 Uiso R . . . . . . H7 H 0.9541 0.7483 0.6087 0.0822 0.5000 Uiso R . . . . . . H8 H 0.9040 0.7990 0.6064 0.0768 0.5000 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 Cu1 0.03153(11) 0.02964(11) 0.02293(10) -0.00010(9) 0.00915(7) -0.00137(9) N1 0.0358(8) 0.0280(7) 0.0253(6) 0.0018(5) 0.0130(6) 0.0085(6) N2 0.0298(7) 0.0238(7) 0.0270(7) -0.0008(5) 0.0090(6) 0.0037(5) N3 0.0267(7) 0.0287(7) 0.0280(7) -0.0037(6) 0.0119(6) -0.0063(6) N4 0.0311(7) 0.0368(8) 0.0260(7) 0.0012(6) 0.0072(6) -0.0111(6) C1 0.0446(10) 0.0331(9) 0.0295(9) 0.0006(7) 0.0155(8) 0.0115(8) C2 0.0435(10) 0.0344(9) 0.0356(9) 0.0015(8) 0.0145(8) 0.0164(8) C3 0.0467(12) 0.0470(11) 0.0388(11) -0.0056(9) 0.0009(9) 0.0240(10) C4 0.0452(12) 0.0428(11) 0.0363(10) -0.0100(9) 0.0028(9) 0.0178(9) C5 0.0331(9) 0.0264(8) 0.0293(8) 0.0002(6) 0.0111(7) 0.0082(6) C6 0.0310(8) 0.0238(8) 0.0283(8) -0.0005(6) 0.0103(7) 0.0057(6) C7 0.0389(10) 0.0365(10) 0.0270(8) -0.0020(7) 0.0063(7) 0.0112(8) C8 0.0396(10) 0.0360(9) 0.0321(9) -0.0061(7) 0.0114(8) 0.0109(8) C9 0.0308(9) 0.0293(8) 0.0351(9) -0.0027(7) 0.0116(7) 0.0058(7) C10 0.0297(8) 0.0283(8) 0.0320(9) -0.0010(7) 0.0090(7) 0.0048(7) C11 0.0545(13) 0.0390(11) 0.0339(10) -0.0020(8) 0.0111(9) 0.0231(10) C12 0.0722(16) 0.0506(13) 0.0354(10) -0.0076(9) 0.0126(10) 0.0267(12) C13 0.0481(12) 0.0536(13) 0.0341(10) -0.0053(9) 0.0017(9) 0.0238(10) C14 0.0363(10) 0.0396(10) 0.0398(10) -0.0047(8) 0.0093(8) 0.0123(8) C15 0.0366(9) 0.0383(9) 0.0327(8) -0.0024(7) 0.0153(7) -0.0125(8) C16 0.0347(9) 0.0349(9) 0.0359(9) -0.0048(7) 0.0123(7) -0.0136(7) C17 0.0366(9) 0.0351(9) 0.0300(8) -0.0076(7) 0.0085(7) -0.0107(8) C18 0.0388(10) 0.0335(9) 0.0263(8) -0.0030(7) 0.0111(7) -0.0103(7) C19 0.0275(8) 0.0259(8) 0.0262(8) -0.0027(6) 0.0102(6) -0.0042(6) C20 0.0302(8) 0.0275(8) 0.0265(8) -0.0030(6) 0.0119(6) -0.0061(6) C21 0.0525(12) 0.0510(12) 0.0266(9) -0.0033(8) 0.0134(8) -0.0228(10) C22 0.0530(12) 0.0473(11) 0.0324(9) 0.0000(8) 0.0188(8) -0.0227(10) C23 0.0446(10) 0.0429(10) 0.0364(9) -0.0028(8) 0.0156(8) -0.0197(9) C24 0.0479(11) 0.0568(13) 0.0318(9) -0.0012(9) 0.0087(8) -0.0280(10) C25 0.0771(17) 0.0882(19) 0.0349(11) -0.0054(12) 0.0239(11) -0.0508(16) C26 0.047(4) 0.053(4) 0.0476(19) -0.0037(15) 0.012(3) -0.0288(17) C27 0.052(2) 0.0450(18) 0.031(2) -0.0039(14) 0.0129(18) -0.0217(14) C28 0.066(3) 0.077(3) 0.0343(15) -0.002(2) 0.0072(18) -0.047(2) C36 0.046(5) 0.054(4) 0.0455(16) -0.0036(19) 0.011(3) -0.030(2) C37 0.0480(17) 0.055(2) 0.041(2) -0.0083(17) 0.0213(16) -0.0248(14) C38 0.060(5) 0.070(6) 0.037(4) 0.004(5) -0.009(4) -0.037(4) O1 0.0458(8) 0.0506(9) 0.0453(8) -0.0054(7) 0.0164(7) 0.0221(7) O2 0.0721(12) 0.0653(11) 0.0449(9) -0.0003(8) 0.0092(8) 0.0436(10) O3 0.0655(11) 0.0368(8) 0.0723(12) -0.0074(8) 0.0020(9) 0.0264(8) O4 0.0506(9) 0.0551(10) 0.0499(9) -0.0074(7) 0.0102(7) 0.0286(8) O5 0.046(4) 0.031(3) 0.0444(16) 0.0022(15) 0.004(3) -0.022(3) O6 0.063(2) 0.065(3) 0.0492(18) 0.0013(18) 0.0189(18) -0.0475(18) O7 0.078(2) 0.067(2) 0.0647(19) -0.0173(15) 0.0456(17) -0.0442(14) O8 0.065(2) 0.0388(15) 0.072(2) -0.0115(15) 0.0215(17) -0.0220(14) O9 0.084(2) 0.0529(16) 0.092(2) 0.0000 0.0090(17) 0.0000 O10 0.135(9) 0.116(8) 0.042(4) -0.008(5) 0.024(5) 0.052(7) O50 0.043(4) 0.046(3) 0.0460(16) 0.0003(18) 0.003(2) -0.025(2) O60 0.087(3) 0.071(3) 0.0552(16) -0.0023(18) 0.029(2) -0.0433(19) O70 0.0431(14) 0.076(2) 0.080(2) -0.0143(17) 0.0298(16) -0.0262(13) O80 0.065(2) 0.0598(17) 0.071(2) 0.0108(15) 0.0269(18) -0.0336(13) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2445(3) 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 Cu1 . N1 . 2.0571(14) yes Cu1 . N2 . 2.0445(14) yes Cu1 . N3 . 2.0359(14) yes Cu1 . N4 . 2.0517(15) yes N1 . C1 . 1.350(2) yes N1 . C5 . 1.351(2) yes N2 . C6 . 1.348(2) yes N2 . C10 . 1.349(2) yes N3 . C15 . 1.353(2) yes N3 . C19 . 1.346(2) yes N4 . C20 . 1.347(2) yes N4 . C24 . 1.344(2) yes C1 . C2 . 1.396(3) yes C1 . C12 . 1.501(3) yes C2 . C3 . 1.384(3) yes C2 . C11 . 1.514(3) yes C3 . C4 . 1.385(3) yes C3 . H31 . 0.938 no C4 . C5 . 1.385(3) yes C4 . H41 . 0.937 no C5 . C6 . 1.487(2) yes C6 . C7 . 1.386(2) yes C7 . C8 . 1.381(3) yes C7 . H71 . 0.915 no C8 . C9 . 1.391(3) yes C8 . H81 . 0.944 no C9 . C10 . 1.410(3) yes C9 . C14 . 1.498(3) yes C10 . C13 . 1.499(3) yes C11 . O3 . 1.272(3) yes C11 . O4 . 1.228(3) yes C12 . H121 . 0.985 no C12 . H122 . 0.973 no C12 . H123 . 0.994 no C13 . H131 . 0.956 no C13 . H132 . 0.949 no C13 . H133 . 0.953 no C14 . O1 . 1.311(3) yes C14 . O2 . 1.211(3) yes C15 . C16 . 1.403(3) yes C15 . C25 . 1.503(3) yes C16 . C17 . 1.382(3) yes C16 . C26 . 1.54(2) yes C16 . C36 . 1.49(2) yes C17 . C18 . 1.387(3) yes C17 . H171 . 0.946 no C18 . C19 . 1.391(2) yes C18 . H181 . 0.912 no C19 . C20 . 1.486(2) yes C20 . C21 . 1.381(3) yes C21 . C22 . 1.382(3) yes C21 . H211 . 0.930 no C22 . C23 . 1.376(3) yes C22 . H231 . 0.954 no C23 . C24 . 1.396(3) yes C23 . C27 . 1.525(6) yes C23 . C37 . 1.536(6) yes C24 . C28 . 1.515(5) yes C24 . C38 . 1.535(16) yes C25 . H251 . 0.960 no C25 . H252 . 0.978 no C25 . H253 . 0.975 no C26 . O5 . 1.31(3) yes C26 . O6 . 1.219(15) yes C27 . O7 . 1.308(7) yes C27 . O8 . 1.191(7) yes C28 . H281 . 0.950 no C28 . H282 . 0.950 no C28 . H283 . 0.950 no C36 . O50 . 1.25(3) yes C36 . O60 . 1.285(15) yes C37 . O70 . 1.208(8) yes C37 . O80 . 1.283(8) yes C38 . H281 . 0.609 no C38 . H381 . 0.950 no C38 . H382 . 0.950 no C38 . H383 . 0.950 no O1 . H1 . 0.802 no O3 . H2 . 0.827 no O7 . H7 . 0.820 no O9 . H4 5_656 0.813 no O9 . H4 . 0.813 no O10 . H6 . 0.820 no O10 . H5 . 0.820 no O80 . H8 . 0.820 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 N1 . Cu1 . N2 . 81.30(6) yes N1 . Cu1 . N3 . 128.59(6) yes N2 . Cu1 . N3 . 133.40(6) yes N1 . Cu1 . N4 . 121.97(6) yes N2 . Cu1 . N4 . 115.34(6) yes N3 . Cu1 . N4 . 81.12(6) yes Cu1 . N1 . C1 . 127.63(12) yes Cu1 . N1 . C5 . 111.43(11) yes C1 . N1 . C5 . 119.82(15) yes Cu1 . N2 . C6 . 112.86(11) yes Cu1 . N2 . C10 . 127.03(12) yes C6 . N2 . C10 . 120.05(15) yes Cu1 . N3 . C15 . 126.20(12) yes Cu1 . N3 . C19 . 113.70(11) yes C15 . N3 . C19 . 119.79(15) yes Cu1 . N4 . C20 . 113.25(11) yes Cu1 . N4 . C24 . 126.53(13) yes C20 . N4 . C24 . 119.65(16) yes N1 . C1 . C2 . 120.43(17) yes N1 . C1 . C12 . 116.37(17) yes C2 . C1 . C12 . 123.21(17) yes C1 . C2 . C3 . 119.32(17) yes C1 . C2 . C11 . 123.80(18) yes C3 . C2 . C11 . 116.86(17) yes C2 . C3 . C4 . 119.82(19) yes C2 . C3 . H31 . 119.2 no C4 . C3 . H31 . 121.0 no C3 . C4 . C5 . 118.27(18) yes C3 . C4 . H41 . 120.7 no C5 . C4 . H41 . 121.0 no C4 . C5 . N1 . 121.92(16) yes C4 . C5 . C6 . 122.35(16) yes N1 . C5 . C6 . 115.73(15) yes C5 . C6 . N2 . 115.86(15) yes C5 . C6 . C7 . 121.97(16) yes N2 . C6 . C7 . 122.15(15) yes C6 . C7 . C8 . 118.41(17) yes C6 . C7 . H71 . 120.6 no C8 . C7 . H71 . 121.0 no C7 . C8 . C9 . 120.22(17) yes C7 . C8 . H81 . 119.5 no C9 . C8 . H81 . 120.3 no C8 . C9 . C10 . 118.56(16) yes C8 . C9 . C14 . 119.53(16) yes C10 . C9 . C14 . 121.90(16) yes C9 . C10 . N2 . 120.54(16) yes C9 . C10 . C13 . 123.91(16) yes N2 . C10 . C13 . 115.54(16) yes C2 . C11 . O3 . 114.67(19) yes C2 . C11 . O4 . 117.9(2) yes O3 . C11 . O4 . 127.33(19) yes C1 . C12 . H121 . 110.1 no C1 . C12 . H122 . 108.7 no H121 . C12 . H122 . 110.4 no C1 . C12 . H123 . 107.4 no H121 . C12 . H123 . 109.7 no H122 . C12 . H123 . 110.5 no C10 . C13 . H131 . 110.5 no C10 . C13 . H132 . 110.4 no H131 . C13 . H132 . 110.7 no C10 . C13 . H133 . 107.4 no H131 . C13 . H133 . 110.2 no H132 . C13 . H133 . 107.6 no C9 . C14 . O1 . 112.81(17) yes C9 . C14 . O2 . 123.07(19) yes O1 . C14 . O2 . 124.06(18) yes N3 . C15 . C16 . 120.73(17) yes N3 . C15 . C25 . 115.03(17) yes C16 . C15 . C25 . 124.24(17) yes C15 . C16 . C17 . 118.92(16) yes C15 . C16 . C26 . 122.7(7) yes C17 . C16 . C26 . 118.3(7) yes C15 . C16 . C36 . 123.5(7) yes C17 . C16 . C36 . 117.3(7) yes C16 . C17 . C18 . 120.18(16) yes C16 . C17 . H171 . 120.3 no C18 . C17 . H171 . 119.5 no C17 . C18 . C19 . 118.23(17) yes C17 . C18 . H181 . 120.3 no C19 . C18 . H181 . 121.4 no C18 . C19 . N3 . 122.07(15) yes C18 . C19 . C20 . 122.04(15) yes N3 . C19 . C20 . 115.87(14) yes C19 . C20 . N4 . 115.39(15) yes C19 . C20 . C21 . 122.71(16) yes N4 . C20 . C21 . 121.90(16) yes C20 . C21 . C22 . 118.74(18) yes C20 . C21 . H211 . 120.6 no C22 . C21 . H211 . 120.7 no C21 . C22 . C23 . 119.61(18) yes C21 . C22 . H231 . 120.4 no C23 . C22 . H231 . 120.0 no C22 . C23 . C24 . 119.29(18) yes C22 . C23 . C27 . 117.6(2) yes C24 . C23 . C27 . 121.7(3) yes C22 . C23 . C37 . 117.5(3) yes C24 . C23 . C37 . 122.2(3) yes C23 . C24 . N4 . 120.79(18) yes C23 . C24 . C28 . 121.5(2) yes N4 . C24 . C28 . 117.4(2) yes C23 . C24 . C38 . 123.0(7) yes N4 . C24 . C38 . 112.5(6) yes C15 . C25 . H251 . 110.6 no C15 . C25 . H252 . 109.2 no H251 . C25 . H252 . 109.5 no C15 . C25 . H253 . 111.8 no H251 . C25 . H253 . 107.7 no H252 . C25 . H253 . 108.0 no C16 . C26 . O5 . 106.8(13) yes C16 . C26 . O6 . 117.8(18) yes O5 . C26 . O6 . 135(2) yes C23 . C27 . O7 . 106.9(4) yes C23 . C27 . O8 . 126.2(5) yes O7 . C27 . O8 . 126.9(5) yes C24 . C28 . H281 . 106.8 no C24 . C28 . H282 . 107.1 no H281 . C28 . H282 . 111.2 no C24 . C28 . H283 . 111.0 no H281 . C28 . H283 . 109.5 no H282 . C28 . H283 . 111.2 no C16 . C36 . O50 . 121.6(15) yes C16 . C36 . O60 . 120.3(17) yes O50 . C36 . O60 . 118(2) yes C23 . C37 . O70 . 125.7(5) yes C23 . C37 . O80 . 108.6(5) yes O70 . C37 . O80 . 125.7(6) yes C24 . C38 . H381 . 108.8 no H281 . C38 . H381 . 115.7 no C24 . C38 . H382 . 126.4 no H281 . C38 . H382 . 46.7 no H381 . C38 . H382 . 109.5 no C24 . C38 . H383 . 97.4 no H381 . C38 . H383 . 106.2 no H382 . C38 . H383 . 106.2 no C14 . O1 . H1 . 105.2 no C11 . O3 . H2 . 119.6 no C27 . O7 . H7 . 119.6 no H4 5_656 O9 . H4 . 98.9 no H6 . O10 . H5 . 109.5 no C37 . O80 . H8 . 119.7 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 O1 . H1 . O4 3_455 163 0.80 1.80 2.578(6) yes O3 . H2 . O5 8_555 168 0.83 1.71 2.522(6) yes O3 . H2 . O50 8_555 163 0.83 1.62 2.424(6) yes O9 . H4 . O2 . 153 0.81 2.11 2.856(6) yes O10 . H6 . O9 . 145 0.82 1.93 2.644(6) yes O10 . H5 . O10 5_656 146 0.82 1.79 2.508(6) yes O7 . H7 . O6 3_555 145 0.82 2.09 2.802(6) yes O7 . H7 . O60 3_555 170 0.82 1.74 2.550(6) yes O80 . H8 . O6 3_555 170 0.82 1.72 2.536(6) yes O80 . H8 . O60 3_555 148 0.82 2.02 2.757(6) yes # Attachment '[H36].cif' data_ah161_2_173k _database_code_depnum_ccdc_archive 'CCDC 717563' _audit_creation_date 08-05-22 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'ah161_2_173k_0m in P-1' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.0489(7) _cell_length_b 9.8221(8) _cell_length_c 17.5416(13) _cell_angle_alpha 93.451(5) _cell_angle_beta 98.501(5) _cell_angle_gamma 95.971(5) _cell_volume 1529.1(2) _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' 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 0.0061 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' 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' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C36 H24 F12 N3 O10 # Dc = 1.93 Fooo = 748.00 Mu = 1.87 M = 886.58 # Found Formula = C30 H19 F9 N2 O10 # Dc = 1.60 FOOO = 748.00 Mu = 1.55 M = 738.47 _chemical_formula_sum 'C30 H19 F9 N2 O10' _chemical_formula_moiety 'C24 H17 N2 O4, 2(C2 H F3 O2), C2 F3 O2' _chemical_compound_source ? _chemical_formula_weight 738.47 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 173 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_min 0.01 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_max 0.31 _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 0.155 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 1.00 _exptl_absorpt_correction_T_max 1.00 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 173 _diffrn_reflns_number 33221 _reflns_number_total 9445 _diffrn_reflns_av_R_equivalents 0.075 # Number of reflections with Friedels Law is 9445 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 9760 _diffrn_reflns_theta_min 2.291 _diffrn_reflns_theta_max 31.013 _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.121 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min -13 _reflns_limit_h_max 12 _reflns_limit_k_min -14 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.62 _refine_diff_density_max 0.62 _refine_ls_number_reflns 4614 _refine_ls_number_restraints 192 _refine_ls_number_parameters 505 #_refine_ls_R_factor_ref 0.0833 _refine_ls_wR_factor_ref 0.0638 _refine_ls_goodness_of_fit_ref 1.2854 #_reflns_number_all 9405 _refine_ls_R_factor_all 0.1798 _refine_ls_wR_factor_all 0.0966 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.0\s(I) _reflns_number_gt 4614 _refine_ls_R_factor_gt 0.0833 _refine_ls_wR_factor_gt 0.0638 _refine_ls_shift/su_max 0.000191 # 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 F _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, 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: 3.24 4.04 2.22 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # 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 _atom_site_attached_hydrogens O1 O -0.2178(2) 0.7232(2) 0.36422(11) 0.0279 1.0000 Uani . . . . . . O2 O -0.1367(2) 0.5799(2) 0.45072(12) 0.0345 1.0000 Uani . . . . . . O3 O 0.6380(3) 0.1605(3) 0.51057(13) 0.0395 1.0000 Uani . . . . . . O4 O 0.4531(2) 0.2425(2) 0.56204(12) 0.0354 1.0000 Uani . . . . . . O5 O 0.5167(3) 0.2127(3) 0.75551(15) 0.0428 1.0000 Uani . . . . . . O6 O 0.4438(3) -0.0047(2) 0.70777(14) 0.0388 1.0000 Uani . . . . . . O7 O 0.7600(3) -0.3448(3) 0.84242(15) 0.0458 1.0000 Uani . . . . . . O8 O 0.6421(3) -0.1578(3) 0.82301(14) 0.0433 1.0000 Uani . . . . . . O9 O 0.7861(3) -0.1339(2) 0.70519(13) 0.0377 1.0000 Uani . . . . . . O10 O 0.6678(3) 0.0079(3) 0.62942(13) 0.0397 1.0000 Uani . . . . . . N1 N 0.2380(2) 0.6011(2) 0.27367(12) 0.0207 1.0000 Uani . . . . . . N2 N 0.4624(2) 0.4602(2) 0.31008(12) 0.0194 1.0000 Uani . . . . . . C1 C 0.1326(3) 0.6761(3) 0.24285(14) 0.0186 1.0000 Uani . . . . . . C2 C 0.0129(3) 0.6923(3) 0.28270(14) 0.0195 1.0000 Uani . . . . . . C3 C 0.0071(3) 0.6303(3) 0.35089(14) 0.0190 1.0000 Uani . . . . . . C4 C 0.1185(3) 0.5508(3) 0.37999(14) 0.0214 1.0000 Uani . . . . . . C5 C 0.2363(3) 0.5364(3) 0.33955(14) 0.0187 1.0000 Uani . . . . . . C6 C 0.3665(3) 0.4588(3) 0.36105(14) 0.0180 1.0000 Uani . . . . . . C7 C 0.3825(3) 0.3892(3) 0.42761(14) 0.0199 1.0000 Uani . . . . . . C8 C 0.5056(3) 0.3157(3) 0.43990(14) 0.0192 1.0000 Uani . . . . . . C9 C 0.6047(3) 0.3162(3) 0.38795(15) 0.0215 1.0000 Uani . . . . . . C10 C 0.5817(3) 0.3908(3) 0.32266(15) 0.0205 1.0000 Uani . . . . . . C11 C -0.1242(3) 0.6416(3) 0.39441(15) 0.0215 1.0000 Uani . . . . . . C12 C 0.5273(3) 0.2360(3) 0.51063(16) 0.0231 1.0000 Uani . . . . . . C13 C 0.1471(3) 0.7345(3) 0.16810(15) 0.0214 1.0000 Uani . . . . . . C14 C 0.0914(3) 0.8573(3) 0.15230(17) 0.0294 1.0000 Uani . . . . . . C15 C 0.1060(4) 0.9119(4) 0.0818(2) 0.0382 1.0000 Uani . . . . . . C16 C 0.1769(4) 0.8443(4) 0.02901(18) 0.0395 1.0000 Uani . . . . . . C17 C 0.2305(4) 0.7211(4) 0.04411(17) 0.0385 1.0000 Uani . . . . . . C18 C 0.2153(3) 0.6651(3) 0.11342(16) 0.0276 1.0000 Uani . . . . . . C19 C 0.6863(3) 0.3969(3) 0.26497(14) 0.0193 1.0000 Uani . . . . . . C20 C 0.6691(3) 0.4849(3) 0.20524(16) 0.0247 1.0000 Uani . . . . . . C21 C 0.7668(3) 0.4906(3) 0.15173(17) 0.0296 1.0000 Uani . . . . . . C22 C 0.8841(3) 0.4104(3) 0.15688(17) 0.0289 1.0000 Uani . . . . . . C23 C 0.9028(3) 0.3223(3) 0.21528(18) 0.0308 1.0000 Uani . . . . . . C24 C 0.8055(3) 0.3159(3) 0.26882(17) 0.0269 1.0000 Uani . . . . . . C25 C 0.4427(3) 0.1039(3) 0.75248(17) 0.0282 1.0000 Uani . . . . . . C26 C 0.3310(4) 0.0797(3) 0.8082(2) 0.0451 1.0000 Uani D U . . . . C27 C 0.6845(3) -0.2600(3) 0.86063(17) 0.0296 1.0000 Uani . . . . . . C28 C 0.6292(5) -0.2606(4) 0.9395(2) 0.0441 1.0000 Uani . . . . . . C29 C 0.7698(3) -0.0649(3) 0.64959(16) 0.0252 1.0000 Uani . . . . . . C30 C 0.8923(3) -0.0651(3) 0.59721(18) 0.0369 1.0000 Uani D U . . . . F1 F 0.2931(3) 0.1939(2) 0.83854(15) 0.0630 1.0000 Uani D U . . . . F2 F 0.1922(4) 0.0271(4) 0.7631(3) 0.0572 0.7000 Uani D U . . . . F3 F 0.3539(6) -0.0152(4) 0.8545(3) 0.0655 0.7000 Uani D U . . . . F4 F 0.6001(3) -0.3878(3) 0.95872(14) 0.0653 1.0000 Uani . . . . . . F5 F 0.7342(4) -0.1978(4) 0.99255(15) 0.1026 1.0000 Uani . . . . . . F6 F 0.5057(4) -0.2050(4) 0.9404(2) 0.0996 1.0000 Uani . . . . . . F7 F 0.9587(5) -0.1804(5) 0.6005(3) 0.0591 0.6500 Uani D U . . . . F8 F 0.8245(4) -0.0792(5) 0.52201(16) 0.0568 0.6500 Uani D U . . . . F9 F 0.9848(6) 0.0399(5) 0.6069(4) 0.0812 0.6500 Uani D U . . . . F11 F 0.2229(11) -0.0154(9) 0.7943(6) 0.0676 0.3000 Uani D U . . . . F12 F 0.4203(10) 0.0494(10) 0.8747(5) 0.0586 0.3000 Uani D U . . . . F17 F 0.9005(8) 0.0440(8) 0.5557(5) 0.0571 0.3500 Uani D U . . . . F18 F 1.0290(7) -0.0299(9) 0.6460(4) 0.0620 0.3500 Uani D U . . . . F19 F 0.9054(11) -0.1768(8) 0.5614(6) 0.0726 0.3500 Uani D U . . . . H1 H 0.3129 0.5936 0.2499 0.0269 1.0000 Uiso R . . . . . H2 H -0.3028 0.7168 0.3758 0.0489 1.0000 Uiso R . . . . . H3 H 0.6527 0.1054 0.5437 0.0690 1.0000 Uiso R . . . . . H4 H 0.5132 -0.0065 0.6826 0.0652 1.0000 Uiso R . . . . . H5 H 0.6687 -0.1452 0.7805 0.0553 1.0000 Uiso R . . . . . H21 H -0.0634 0.7426 0.2629 0.0270 1.0000 Uiso R . . . . . H41 H 0.1132 0.5087 0.4254 0.0272 1.0000 Uiso R . . . . . H71 H 0.3144 0.3898 0.4623 0.0249 1.0000 Uiso R . . . . . H91 H 0.6886 0.2690 0.3966 0.0295 1.0000 Uiso R . . . . . H141 H 0.0436 0.9021 0.1881 0.0380 1.0000 Uiso R . . . . . H151 H 0.0691 0.9954 0.0708 0.0499 1.0000 Uiso R . . . . . H161 H 0.1886 0.8827 -0.0176 0.0520 1.0000 Uiso R . . . . . H171 H 0.2772 0.6746 0.0077 0.0508 1.0000 Uiso R . . . . . H181 H 0.2511 0.5824 0.1238 0.0379 1.0000 Uiso R . . . . . H201 H 0.5917 0.5404 0.2023 0.0339 1.0000 Uiso R . . . . . H211 H 0.7522 0.5475 0.1116 0.0388 1.0000 Uiso R . . . . . H221 H 0.9524 0.4182 0.1218 0.0370 1.0000 Uiso R . . . . . H231 H 0.9822 0.2675 0.2185 0.0409 1.0000 Uiso R . . . . . H241 H 0.8192 0.2568 0.3084 0.0368 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 0.0225(9) 0.0392(11) 0.0288(10) 0.0134(9) 0.0140(8) 0.0147(8) O2 0.0329(11) 0.0530(14) 0.0267(10) 0.0182(10) 0.0183(9) 0.0185(10) O3 0.0430(13) 0.0558(14) 0.0331(11) 0.0269(10) 0.0219(10) 0.0319(11) O4 0.0356(12) 0.0515(14) 0.0291(11) 0.0199(10) 0.0196(9) 0.0209(10) O5 0.0359(12) 0.0400(13) 0.0491(14) 0.0050(11) 0.0045(10) -0.0088(11) O6 0.0429(13) 0.0339(12) 0.0459(13) 0.0056(10) 0.0245(11) 0.0080(10) O7 0.0520(15) 0.0472(14) 0.0476(14) 0.0187(11) 0.0218(12) 0.0209(12) O8 0.0594(16) 0.0449(14) 0.0348(12) 0.0153(10) 0.0219(11) 0.0215(12) O9 0.0464(13) 0.0431(13) 0.0295(10) 0.0147(10) 0.0128(10) 0.0169(10) O10 0.0440(13) 0.0515(14) 0.0364(12) 0.0262(10) 0.0242(10) 0.0264(11) N1 0.0191(10) 0.0250(11) 0.0206(11) 0.0048(9) 0.0084(8) 0.0051(9) N2 0.0188(10) 0.0228(11) 0.0184(10) 0.0041(8) 0.0061(8) 0.0046(8) C1 0.0213(12) 0.0199(12) 0.0171(11) 0.0058(9) 0.0090(9) 0.0029(10) C2 0.0193(12) 0.0210(13) 0.0203(11) 0.0053(9) 0.0072(9) 0.0045(10) C3 0.0188(12) 0.0225(12) 0.0173(10) 0.0003(10) 0.0065(9) 0.0058(10) C4 0.0216(12) 0.0274(14) 0.0182(11) 0.0051(10) 0.0088(9) 0.0074(10) C5 0.0181(11) 0.0245(13) 0.0142(10) 0.0051(9) 0.0031(9) 0.0022(10) C6 0.0169(12) 0.0177(12) 0.0216(11) 0.0048(10) 0.0067(9) 0.0047(9) C7 0.0201(12) 0.0215(13) 0.0202(11) 0.0014(10) 0.0084(9) 0.0051(10) C8 0.0195(12) 0.0184(12) 0.0200(11) 0.0048(10) 0.0011(10) 0.0042(10) C9 0.0214(12) 0.0243(13) 0.0220(12) 0.0046(10) 0.0084(10) 0.0089(10) C10 0.0172(11) 0.0220(13) 0.0238(12) 0.0037(10) 0.0056(9) 0.0043(10) C11 0.0208(12) 0.0269(13) 0.0188(11) 0.0010(10) 0.0092(9) 0.0042(10) C12 0.0222(12) 0.0245(13) 0.0254(12) 0.0077(11) 0.0053(10) 0.0105(10) C13 0.0170(11) 0.0301(15) 0.0185(11) 0.0086(10) 0.0041(9) 0.0038(10) C14 0.0303(14) 0.0315(15) 0.0287(14) 0.0079(12) 0.0081(11) 0.0065(12) C15 0.0428(18) 0.0396(18) 0.0341(16) 0.0187(14) 0.0045(13) 0.0062(14) C16 0.0454(19) 0.050(2) 0.0247(14) 0.0151(14) 0.0091(13) 0.0004(16) C17 0.0451(18) 0.057(2) 0.0172(13) 0.0080(13) 0.0135(12) 0.0089(16) C18 0.0288(14) 0.0312(15) 0.0258(13) 0.0053(11) 0.0111(11) 0.0057(11) C19 0.0198(12) 0.0234(12) 0.0168(11) 0.0022(9) 0.0068(9) 0.0062(10) C20 0.0238(13) 0.0284(14) 0.0252(12) 0.0032(11) 0.0101(10) 0.0079(11) C21 0.0314(15) 0.0366(16) 0.0240(13) 0.0064(12) 0.0113(11) 0.0069(13) C22 0.0308(15) 0.0316(15) 0.0263(13) -0.0029(12) 0.0147(11) 0.0017(12) C23 0.0273(14) 0.0329(16) 0.0368(16) 0.0040(13) 0.0160(12) 0.0084(12) C24 0.0310(14) 0.0274(15) 0.0271(13) 0.0087(11) 0.0118(11) 0.0115(11) C25 0.0230(13) 0.0339(16) 0.0301(14) 0.0070(12) 0.0079(11) 0.0068(12) C26 0.054(2) 0.0377(18) 0.056(2) 0.0171(16) 0.0341(18) 0.0196(16) C27 0.0285(14) 0.0337(15) 0.0275(14) 0.0079(12) 0.0052(11) 0.0032(12) C28 0.055(2) 0.047(2) 0.0347(17) 0.0097(15) 0.0203(16) 0.0033(17) C29 0.0295(14) 0.0269(14) 0.0222(12) 0.0042(11) 0.0091(10) 0.0081(11) C30 0.0308(16) 0.0494(19) 0.0368(16) 0.0137(15) 0.0143(13) 0.0150(14) F1 0.0794(17) 0.0538(13) 0.0690(15) 0.0078(11) 0.0430(13) 0.0233(12) F2 0.0461(18) 0.050(2) 0.087(3) 0.0205(18) 0.0382(17) 0.0118(15) F3 0.082(3) 0.060(2) 0.076(3) 0.048(2) 0.052(2) 0.0299(19) F4 0.0895(19) 0.0614(15) 0.0535(14) 0.0285(12) 0.0317(13) 0.0056(13) F5 0.127(3) 0.134(3) 0.0331(13) -0.0112(15) 0.0207(16) -0.054(2) F6 0.124(3) 0.120(3) 0.095(2) 0.061(2) 0.088(2) 0.073(2) F7 0.067(3) 0.072(2) 0.055(2) 0.0174(19) 0.0298(19) 0.048(2) F8 0.0492(19) 0.106(3) 0.0233(14) 0.0042(16) 0.0158(13) 0.032(2) F9 0.071(3) 0.079(3) 0.092(3) -0.028(3) 0.052(3) -0.032(2) F11 0.083(5) 0.051(4) 0.081(5) 0.020(4) 0.058(4) -0.010(4) F12 0.074(5) 0.059(5) 0.062(4) 0.036(4) 0.048(3) 0.027(4) F17 0.047(3) 0.081(4) 0.064(4) 0.051(3) 0.041(3) 0.027(3) F18 0.032(3) 0.087(5) 0.071(4) 0.023(4) 0.018(3) 0.004(3) F19 0.064(5) 0.073(4) 0.085(5) -0.018(4) 0.042(4) 0.001(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3012(9) 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 . C11 . 1.304(3) yes O1 . H2 . 0.821 no O2 . C11 . 1.203(3) yes O3 . C12 . 1.307(3) yes O3 . H3 . 0.823 no O4 . C12 . 1.204(3) yes O5 . C25 . 1.195(4) yes O6 . C25 . 1.287(4) yes O6 . H4 . 0.821 no O7 . C27 . 1.189(4) yes O8 . C27 . 1.294(4) yes O8 . H5 . 0.830 no O9 . C29 . 1.221(3) yes O10 . C29 . 1.249(3) yes N1 . C1 . 1.337(3) yes N1 . C5 . 1.353(3) yes N1 . H1 . 0.854 no N2 . C6 . 1.335(3) yes N2 . C10 . 1.334(3) yes C1 . C2 . 1.390(3) yes C1 . C13 . 1.480(3) yes C2 . C3 . 1.380(3) yes C2 . H21 . 0.929 no C3 . C4 . 1.396(4) yes C3 . C11 . 1.514(3) yes C4 . C5 . 1.379(3) yes C4 . H41 . 0.925 no C5 . C6 . 1.484(3) yes C6 . C7 . 1.385(3) yes C7 . C8 . 1.386(3) yes C7 . H71 . 0.929 no C8 . C9 . 1.370(3) yes C8 . C12 . 1.506(3) yes C9 . C10 . 1.398(4) yes C9 . H91 . 0.928 no C10 . C19 . 1.484(3) yes C13 . C14 . 1.383(4) yes C13 . C18 . 1.396(4) yes C14 . C15 . 1.396(4) yes C14 . H141 . 0.928 no C15 . C16 . 1.378(5) yes C15 . H151 . 0.937 no C16 . C17 . 1.376(5) yes C16 . H161 . 0.936 no C17 . C18 . 1.383(4) yes C17 . H171 . 0.938 no C18 . H181 . 0.923 no C19 . C20 . 1.399(4) yes C19 . C24 . 1.402(4) yes C20 . C21 . 1.381(4) yes C20 . H201 . 0.929 no C21 . C22 . 1.382(4) yes C21 . H211 . 0.927 no C22 . C23 . 1.383(4) yes C22 . H221 . 0.936 no C23 . C24 . 1.379(4) yes C23 . H231 . 0.939 no C24 . H241 . 0.933 no C25 . C26 . 1.518(4) yes C26 . F1 . 1.312(4) yes C26 . F2 . 1.412(5) yes C26 . F3 . 1.285(4) yes C26 . F11 . 1.265(8) yes C26 . F12 . 1.383(8) yes C27 . C28 . 1.540(4) yes C28 . F4 . 1.323(4) yes C28 . F5 . 1.303(5) yes C28 . F6 . 1.296(5) yes C29 . C30 . 1.540(4) yes C30 . F7 . 1.336(5) yes C30 . F8 . 1.363(4) yes C30 . F9 . 1.245(5) yes C30 . F17 . 1.333(6) yes C30 . F18 . 1.395(7) yes C30 . F19 . 1.256(7) yes 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 C11 . O1 . H2 . 118.1 no C12 . O3 . H3 . 120.2 no C25 . O6 . H4 . 117.3 no C27 . O8 . H5 . 119.9 no C1 . N1 . C5 . 125.5(2) yes C1 . N1 . H1 . 117.3 no C5 . N1 . H1 . 117.3 no C6 . N2 . C10 . 119.2(2) yes N1 . C1 . C2 . 117.5(2) yes N1 . C1 . C13 . 118.8(2) yes C2 . C1 . C13 . 123.7(2) yes C1 . C2 . C3 . 119.3(2) yes C1 . C2 . H21 . 120.2 no C3 . C2 . H21 . 120.5 no C2 . C3 . C4 . 121.0(2) yes C2 . C3 . C11 . 120.8(2) yes C4 . C3 . C11 . 118.1(2) yes C3 . C4 . C5 . 118.6(2) yes C3 . C4 . H41 . 120.6 no C5 . C4 . H41 . 120.9 no C4 . C5 . N1 . 118.1(2) yes C4 . C5 . C6 . 127.0(2) yes N1 . C5 . C6 . 114.9(2) yes C5 . C6 . N2 . 114.1(2) yes C5 . C6 . C7 . 121.9(2) yes N2 . C6 . C7 . 124.0(2) yes C6 . C7 . C8 . 116.6(2) yes C6 . C7 . H71 . 122.5 no C8 . C7 . H71 . 120.9 no C7 . C8 . C9 . 119.9(2) yes C7 . C8 . C12 . 119.0(2) yes C9 . C8 . C12 . 121.1(2) yes C8 . C9 . C10 . 120.0(2) yes C8 . C9 . H91 . 120.2 no C10 . C9 . H91 . 119.8 no C9 . C10 . N2 . 120.3(2) yes C9 . C10 . C19 . 122.5(2) yes N2 . C10 . C19 . 117.2(2) yes C3 . C11 . O1 . 112.9(2) yes C3 . C11 . O2 . 121.6(2) yes O1 . C11 . O2 . 125.5(2) yes C8 . C12 . O3 . 112.2(2) yes C8 . C12 . O4 . 124.0(2) yes O3 . C12 . O4 . 123.7(2) yes C1 . C13 . C14 . 119.7(2) yes C1 . C13 . C18 . 120.2(2) yes C14 . C13 . C18 . 120.1(2) yes C13 . C14 . C15 . 119.4(3) yes C13 . C14 . H141 . 120.1 no C15 . C14 . H141 . 120.6 no C14 . C15 . C16 . 120.0(3) yes C14 . C15 . H151 . 119.8 no C16 . C15 . H151 . 120.2 no C15 . C16 . C17 . 120.7(3) yes C15 . C16 . H161 . 119.5 no C17 . C16 . H161 . 119.8 no C16 . C17 . C18 . 119.8(3) yes C16 . C17 . H171 . 120.4 no C18 . C17 . H171 . 119.7 no C13 . C18 . C17 . 119.9(3) yes C13 . C18 . H181 . 120.0 no C17 . C18 . H181 . 120.1 no C10 . C19 . C20 . 120.7(2) yes C10 . C19 . C24 . 121.3(2) yes C20 . C19 . C24 . 118.0(2) yes C19 . C20 . C21 . 120.6(3) yes C19 . C20 . H201 . 119.2 no C21 . C20 . H201 . 120.2 no C20 . C21 . C22 . 120.4(3) yes C20 . C21 . H211 . 119.6 no C22 . C21 . H211 . 120.0 no C21 . C22 . C23 . 119.9(2) yes C21 . C22 . H221 . 119.7 no C23 . C22 . H221 . 120.3 no C22 . C23 . C24 . 119.9(3) yes C22 . C23 . H231 . 119.8 no C24 . C23 . H231 . 120.3 no C19 . C24 . C23 . 121.1(3) yes C19 . C24 . H241 . 119.4 no C23 . C24 . H241 . 119.6 no O6 . C25 . O5 . 129.2(3) yes O6 . C25 . C26 . 111.1(3) yes O5 . C25 . C26 . 119.8(3) yes C25 . C26 . F1 . 113.1(3) yes C25 . C26 . F2 . 106.7(3) yes F1 . C26 . F2 . 99.7(3) yes C25 . C26 . F3 . 116.5(3) yes F1 . C26 . F3 . 116.1(3) yes F2 . C26 . F3 . 102.0(4) yes C25 . C26 . F11 . 121.5(5) yes F1 . C26 . F11 . 113.1(6) yes C25 . C26 . F12 . 103.1(4) yes F1 . C26 . F12 . 95.4(5) yes F11 . C26 . F12 . 106.3(7) yes O8 . C27 . O7 . 128.5(3) yes O8 . C27 . C28 . 111.5(3) yes O7 . C27 . C28 . 120.0(3) yes C27 . C28 . F4 . 110.8(3) yes C27 . C28 . F5 . 109.3(3) yes F4 . C28 . F5 . 107.6(3) yes C27 . C28 . F6 . 113.3(3) yes F4 . C28 . F6 . 105.8(3) yes F5 . C28 . F6 . 109.8(4) yes O10 . C29 . O9 . 128.9(3) yes O10 . C29 . C30 . 114.9(2) yes O9 . C29 . C30 . 116.2(3) yes C29 . C30 . F7 . 111.5(3) yes C29 . C30 . F8 . 108.7(3) yes F7 . C30 . F8 . 100.1(4) yes C29 . C30 . F9 . 114.4(3) yes F7 . C30 . F9 . 112.5(4) yes F8 . C30 . F9 . 108.6(4) yes C29 . C30 . F17 . 113.3(3) yes C29 . C30 . F18 . 106.0(4) yes F17 . C30 . F18 . 96.7(5) yes C29 . C30 . F19 . 117.6(5) yes F17 . C30 . F19 . 114.8(7) yes F18 . C30 . F19 . 105.4(6) yes 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 O1 . H2 . O4 2_566 155 0.82 1.92 2.689(2) yes O3 . H3 . O10 . 168 0.82 1.83 2.638(2) yes O6 . H4 . O10 . 174 0.82 1.79 2.609(2) yes O8 . H5 . O9 . 160 0.83 1.81 2.611(2) yes # Attachment 'compound_5.cif' data_ah156 _database_code_depnum_ccdc_archive 'CCDC 717564' _audit_creation_date 07-02-21 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title '2211152 ah156_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 33.495(2) _cell_length_b 33.495(2) _cell_length_c 5.1499(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 5003.7(5) _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'R -3 ' _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/3,y+2/3,z+2/3 -x+1/3,-y+2/3,-z+2/3 x+2/3,y+1/3,z+1/3 -x+2/3,-y+1/3,-z+1/3 -y,x-y,z y,-x+y,-z -y+1/3,x-y+2/3,z+2/3 y+1/3,-x+y+2/3,-z+2/3 -y+2/3,x-y+1/3,z+1/3 y+2/3,-x+y+1/3,-z+1/3 -x+y,-x,z x-y,x,-z -x+y+1/3,-x+2/3,z+2/3 x-y+1/3,x+2/3,-z+2/3 -x+y+2/3,-x+1/3,z+1/3 x-y+2/3,x+1/3,-z+1/3 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' 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' 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' _cell_formula_units_Z 9 # Given Formula = C30 H20 N2 O2 # Dc = 1.32 Fooo = 2070.00 Mu = 0.83 M = 220.25 # Found Formula = C30 H20 N2 O2 # Dc = 1.32 FOOO = 2070.00 Mu = 0.83 M = 220.25 _chemical_formula_sum 'C30 H20 N2 O2' _chemical_formula_moiety 'C30 H20 N2 O2' _chemical_compound_source ? _chemical_formula_weight 440.50 _cell_measurement_reflns_used 8865 _cell_measurement_theta_min 1 _cell_measurement_theta_max 26 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 2070 _exptl_absorpt_coefficient_mu 0.083 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 173 _diffrn_reflns_number 21185 _reflns_number_total 2084 _diffrn_reflns_av_R_equivalents 0.050 # Number of reflections with Friedels Law is 2084 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2200 _diffrn_reflns_theta_min 2.432 _diffrn_reflns_theta_max 26.060 _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 25.017 _diffrn_measured_fraction_theta_full 0.949 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 5 _reflns_limit_h_min -40 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 41 _reflns_limit_l_min 0 _reflns_limit_l_max 6 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.30 _refine_diff_density_max 0.33 _refine_ls_number_reflns 2064 _refine_ls_number_restraints 0 _refine_ls_number_parameters 155 #_refine_ls_R_factor_ref 0.0773 _refine_ls_wR_factor_ref 0.0800 _refine_ls_goodness_of_fit_ref 1.0180 #_reflns_number_all 2064 _refine_ls_R_factor_all 0.0773 _refine_ls_wR_factor_all 0.0800 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1195 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_gt 0.0554 _refine_ls_shift/su_max 0.000362 # 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, 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: 5.43 6.23 1.57 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # 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 _atom_site_attached_hydrogens O1 O 0.33364(5) 0.44099(6) 0.0194(3) 0.0548 1.0000 Uani . . . . . . N1 N 0.46916(6) 0.52756(6) 0.6189(4) 0.0420 1.0000 Uani . . . . . . C1 C 0.45093(8) 0.58300(8) 0.9478(4) 0.0476 1.0000 Uani . . . . . . C2 C 0.44391(9) 0.61364(8) 1.0948(5) 0.0534 1.0000 Uani . . . . . . C3 C 0.40793(9) 0.62082(9) 1.0374(5) 0.0570 1.0000 Uani . . . . . . C4 C 0.37901(9) 0.59826(9) 0.8335(5) 0.0578 1.0000 Uani . . . . . . C5 C 0.38531(8) 0.56726(8) 0.6874(5) 0.0513 1.0000 Uani . . . . . . C6 C 0.42125(7) 0.55916(7) 0.7417(4) 0.0421 1.0000 Uani . . . . . . C7 C 0.42896(7) 0.52666(7) 0.5807(4) 0.0412 1.0000 Uani . . . . . . C8 C 0.39667(8) 0.49757(7) 0.3982(4) 0.0432 1.0000 Uani . . . . . . C9 C 0.40620(7) 0.46938(7) 0.2436(4) 0.0411 1.0000 Uani . . . . . . C10 C 0.44788(7) 0.47047(7) 0.2828(4) 0.0406 1.0000 Uani . . . . . . C11 C 0.47783(7) 0.49919(7) 0.4728(4) 0.0409 1.0000 Uani . . . . . . C12 C 0.37362(7) 0.43932(7) 0.0466(5) 0.0425 1.0000 Uani . . . . . . C13 C 0.37381(8) 0.40889(8) -0.1255(5) 0.0485 1.0000 Uani . . . . . . C14 C 0.33160(9) 0.39055(8) -0.2682(5) 0.0534 1.0000 Uani . . . . . . C15 C 0.30877(8) 0.41085(9) -0.1751(5) 0.0563 1.0000 Uani . . . . . . H11 H 0.4752 0.5777 0.9872 0.0543 1.0000 Uiso R . . . . . H21 H 0.4637 0.6294 1.2375 0.0590 1.0000 Uiso R . . . . . H31 H 0.4031 0.6414 1.1384 0.0658 1.0000 Uiso R . . . . . H41 H 0.3548 0.6041 0.7902 0.0698 1.0000 Uiso R . . . . . H51 H 0.3645 0.5514 0.5477 0.0615 1.0000 Uiso R . . . . . H81 H 0.3685 0.4970 0.3789 0.0500 1.0000 Uiso R . . . . . H101 H 0.4555 0.4522 0.1782 0.0490 1.0000 Uiso R . . . . . H131 H 0.3969 0.4019 -0.1501 0.0588 1.0000 Uiso R . . . . . H141 H 0.3220 0.3686 -0.4003 0.0595 1.0000 Uiso R . . . . . H151 H 0.2804 0.4076 -0.2239 0.0634 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 0.0446(9) 0.0560(10) 0.0658(11) -0.0139(8) -0.0149(8) 0.0266(8) N1 0.0393(10) 0.0380(10) 0.0473(11) 0.0016(8) -0.0035(8) 0.0183(8) C1 0.0456(13) 0.0416(12) 0.0489(14) 0.0017(10) 0.0015(11) 0.0168(11) C2 0.0510(14) 0.0461(14) 0.0497(15) -0.0058(11) 0.0026(11) 0.0143(12) C3 0.0524(15) 0.0484(14) 0.0624(17) -0.0073(12) 0.0106(13) 0.0192(12) C4 0.0488(14) 0.0565(15) 0.0679(18) -0.0054(13) 0.0045(13) 0.0262(12) C5 0.0458(13) 0.0521(14) 0.0557(16) -0.0053(11) -0.0009(11) 0.0242(12) C6 0.0391(12) 0.0375(12) 0.0447(13) 0.0039(10) 0.0018(10) 0.0154(10) C7 0.0405(12) 0.0364(11) 0.0451(14) 0.0033(9) -0.0015(10) 0.0181(10) C8 0.0371(12) 0.0399(12) 0.0511(14) 0.0030(10) -0.0040(10) 0.0180(10) C9 0.0401(12) 0.0358(11) 0.0440(13) 0.0029(9) -0.0045(10) 0.0164(10) C10 0.0410(12) 0.0356(11) 0.0453(13) 0.0003(9) -0.0058(10) 0.0193(10) C11 0.0396(12) 0.0367(11) 0.0449(13) 0.0039(9) -0.0034(10) 0.0180(10) C12 0.0371(12) 0.0389(12) 0.0488(14) 0.0027(10) -0.0049(10) 0.0170(10) C13 0.0470(13) 0.0479(13) 0.0524(15) 0.0034(11) 0.0002(11) 0.0252(11) C14 0.0545(15) 0.0465(14) 0.0477(15) -0.0056(11) -0.0100(11) 0.0167(12) C15 0.0440(14) 0.0555(15) 0.0620(17) -0.0098(12) -0.0183(12) 0.0194(12) _refine_ls_extinction_coef 150(10) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.18349(15) 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 . C12 . 1.375(2) yes O1 . C15 . 1.370(3) yes N1 . C7 . 1.346(3) yes N1 . C11 . 1.352(3) yes C1 . C2 . 1.387(3) yes C1 . C6 . 1.399(3) yes C1 . H11 . 0.939 no C2 . C3 . 1.374(4) yes C2 . H21 . 0.953 no C3 . C4 . 1.371(3) yes C3 . H31 . 0.940 no C4 . C5 . 1.381(3) yes C4 . H41 . 0.951 no C5 . C6 . 1.389(3) yes C5 . H51 . 0.957 no C6 . C7 . 1.490(3) yes C7 . C8 . 1.396(3) yes C8 . C9 . 1.389(3) yes C8 . H81 . 0.939 no C9 . C10 . 1.393(3) yes C9 . C12 . 1.461(3) yes C10 . C11 . 1.387(3) yes C10 . H101 . 0.942 no C11 . C11 2_666 1.486(4) yes C12 . C13 . 1.353(3) yes C13 . C14 . 1.431(3) yes C13 . H131 . 0.921 no C14 . C15 . 1.340(4) yes C14 . H141 . 0.933 no C15 . H151 . 0.936 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 C12 . O1 . C15 . 106.87(18) yes C7 . N1 . C11 . 117.82(18) yes C2 . C1 . C6 . 120.1(2) yes C2 . C1 . H11 . 120.5 no C6 . C1 . H11 . 119.4 no C1 . C2 . C3 . 120.0(2) yes C1 . C2 . H21 . 120.2 no C3 . C2 . H21 . 119.7 no C2 . C3 . C4 . 120.5(2) yes C2 . C3 . H31 . 119.8 no C4 . C3 . H31 . 119.7 no C3 . C4 . C5 . 120.0(3) yes C3 . C4 . H41 . 120.4 no C5 . C4 . H41 . 119.6 no C4 . C5 . C6 . 120.7(2) yes C4 . C5 . H51 . 118.9 no C6 . C5 . H51 . 120.4 no C1 . C6 . C5 . 118.6(2) yes C1 . C6 . C7 . 120.4(2) yes C5 . C6 . C7 . 121.0(2) yes C6 . C7 . N1 . 116.05(19) yes C6 . C7 . C8 . 121.9(2) yes N1 . C7 . C8 . 122.1(2) yes C7 . C8 . C9 . 120.0(2) yes C7 . C8 . H81 . 120.4 no C9 . C8 . H81 . 119.7 no C8 . C9 . C10 . 117.8(2) yes C8 . C9 . C12 . 121.3(2) yes C10 . C9 . C12 . 120.8(2) yes C9 . C10 . C11 . 119.2(2) yes C9 . C10 . H101 . 119.7 no C11 . C10 . H101 . 121.1 no C11 2_666 C11 . C10 . 121.4(2) yes C11 2_666 C11 . N1 . 115.6(2) yes C10 . C11 . N1 . 123.01(19) yes C9 . C12 . O1 . 116.71(19) yes C9 . C12 . C13 . 133.7(2) yes O1 . C12 . C13 . 109.6(2) yes C12 . C13 . C14 . 106.5(2) yes C12 . C13 . H131 . 126.9 no C14 . C13 . H131 . 126.5 no C13 . C14 . C15 . 106.9(2) yes C13 . C14 . H141 . 126.2 no C15 . C14 . H141 . 127.0 no O1 . C15 . C14 . 110.1(2) yes O1 . C15 . H151 . 119.3 no C14 . C15 . H151 . 130.5 no # Attachment 'ligand_3.cif' data_ah038 _database_code_depnum_ccdc_archive 'CCDC 717565' _audit_creation_date 06-02-21 _audit_creation_method CRYSTALS_ver_12.24 _oxford_structure_analysis_title '2211012 ah038_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.51940(10) _cell_length_b 12.1847(2) _cell_length_c 19.5707(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1554.64(4) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P c a b ' _symmetry_space_group_name_Hall '-P 2bc 2ac' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y,z+1/2 x+1/2,-y,-z+1/2 x+1/2,-y+1/2,z -x+1/2,y+1/2,-z -x,-y+1/2,z+1/2 x,y+1/2,-z+1/2 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' 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' 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' _cell_formula_units_Z 4 _chemical_formula_sum 'C20 H16 N2 O2' _chemical_formula_moiety 'C20 H16 N2 O2' _chemical_compound_source ? _chemical_formula_weight 316.36 _cell_measurement_reflns_used 6766 _cell_measurement_theta_min 1 _cell_measurement_theta_max 28 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.04 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_max 0.21 _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 1.00 # Sheldrick geometric definitions 0.99 1.00 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 173 _diffrn_reflns_number 13630 _reflns_number_total 1855 _diffrn_reflns_av_R_equivalents 0.071 # Number of reflections with Friedels Law is 1855 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1853 _diffrn_reflns_theta_min 2.081 _diffrn_reflns_theta_max 27.868 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.868 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.21 _refine_diff_density_max 0.24 _refine_ls_number_reflns 1101 _refine_ls_number_restraints 0 _refine_ls_number_parameters 109 #_refine_ls_R_factor_ref 0.0408 _refine_ls_wR_factor_ref 0.0349 _refine_ls_goodness_of_fit_ref 1.1205 #_reflns_number_all 1844 _refine_ls_R_factor_all 0.0641 _refine_ls_wR_factor_all 0.0416 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.50u(I) _reflns_number_gt 1101 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_gt 0.0349 _refine_ls_shift/su_max 0.000368 # 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 F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _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: -0.606E-02 -0.655 -0.355 -0.344 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, (1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached 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 _atom_site_attached_hydrogens O1 O 0.6175(2) 0.08450(11) 0.69342(6) 0.0456 1.0000 Uani . . . . . . N1 N 0.82494(19) 0.07373(10) 0.44504(6) 0.0283 1.0000 Uani . . . . . . C1 C 0.4858(4) 0.10186(18) 0.74607(10) 0.0535 1.0000 Uani . . . . . . C2 C 0.3099(4) 0.14236(16) 0.72317(10) 0.0558 1.0000 Uani . . . . . . C3 C 0.3277(3) 0.15308(14) 0.64968(9) 0.0410 1.0000 Uani . . . . . . C4 C 0.5182(3) 0.11676(12) 0.63509(8) 0.0310 1.0000 Uani . . . . . . C5 C 0.6258(2) 0.10412(12) 0.57040(8) 0.0283 1.0000 Uani . . . . . . C6 C 0.5456(2) 0.14688(12) 0.51029(8) 0.0312 1.0000 Uani . . . . . . C7 C 0.6482(2) 0.12985(12) 0.44905(8) 0.0298 1.0000 Uani . . . . . . C8 C 0.5611(3) 0.17272(15) 0.38313(8) 0.0389 1.0000 Uani . . . . . . C9 C 0.9030(2) 0.03217(11) 0.50324(7) 0.0269 1.0000 Uani . . . . . . C10 C 0.8104(2) 0.04621(12) 0.56659(8) 0.0291 1.0000 Uani . . . . . . H111 H 0.5218 0.0812 0.7939 0.0695 1.0000 Uiso R . . . . . H121 H 0.1953 0.1639 0.7491 0.0667 1.0000 Uiso R . . . . . H131 H 0.2330 0.1793 0.6194 0.0500 1.0000 Uiso R . . . . . H161 H 0.4178 0.1926 0.5109 0.0377 1.0000 Uiso R . . . . . H181 H 0.5494 0.2524 0.3843 0.0498 1.0000 Uiso R . . . . . H182 H 0.6477 0.1587 0.3443 0.0506 1.0000 Uiso R . . . . . H183 H 0.4280 0.1435 0.3738 0.0516 1.0000 Uiso R . . . . . H201 H 0.8708 0.0126 0.6073 0.0339 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 0.0509(8) 0.0547(7) 0.0310(6) 0.0027(6) 0.0023(5) 0.0031(6) N1 0.0261(6) 0.0320(6) 0.0268(6) 0.0017(5) -0.0006(5) -0.0011(5) C1 0.0679(14) 0.0578(11) 0.0348(9) 0.0020(8) 0.0137(10) -0.0014(11) C2 0.0645(15) 0.0497(10) 0.0532(12) -0.0112(9) 0.0338(11) -0.0042(10) C3 0.0374(9) 0.0369(8) 0.0487(10) -0.0008(7) 0.0118(7) 0.0064(7) C4 0.0350(8) 0.0291(7) 0.0289(7) 0.0000(6) 0.0027(6) 0.0013(6) C5 0.0268(8) 0.0287(7) 0.0293(7) -0.0014(5) 0.0022(6) -0.0015(6) C6 0.0285(8) 0.0314(7) 0.0338(8) 0.0018(6) 0.0006(6) 0.0032(6) C7 0.0280(7) 0.0313(7) 0.0302(8) 0.0032(6) -0.0015(6) -0.0008(6) C8 0.0360(9) 0.0489(10) 0.0318(8) 0.0061(7) -0.0020(7) 0.0056(7) C9 0.0242(7) 0.0289(6) 0.0275(7) -0.0002(5) -0.0003(5) -0.0026(6) C10 0.0276(7) 0.0320(7) 0.0277(7) 0.0027(6) 0.0000(6) 0.0004(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4537(10) 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 . C1 . 1.358(2) yes O1 . C4 . 1.370(2) yes N1 . C7 . 1.342(2) yes N1 . C9 . 1.3465(19) yes C1 . C2 . 1.326(3) yes C1 . H111 . 0.997 no C2 . C3 . 1.449(3) yes C2 . H121 . 0.941 no C3 . C4 . 1.349(3) yes C3 . H131 . 0.914 no C4 . C5 . 1.455(2) yes C5 . C6 . 1.389(2) yes C5 . C10 . 1.397(2) yes C6 . C7 . 1.388(2) yes C6 . H161 . 1.002 no C7 . C8 . 1.503(2) yes C8 . H181 . 0.974 no C8 . H182 . 0.962 no C8 . H183 . 0.956 no C9 . C9 2_756 1.493(3) yes C9 . C10 . 1.390(2) yes C10 . H201 . 0.978 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 C1 . O1 . C4 . 106.77(16) yes C7 . N1 . C9 . 117.82(13) yes O1 . C1 . C2 . 110.39(17) yes O1 . C1 . H111 . 121.581 no C2 . C1 . H111 . 127.925 no C1 . C2 . C3 . 107.45(17) yes C1 . C2 . H121 . 127.424 no C3 . C2 . H121 . 125.067 no C2 . C3 . C4 . 104.72(18) yes C2 . C3 . H131 . 128.454 no C4 . C3 . H131 . 126.817 no O1 . C4 . C3 . 110.66(14) yes O1 . C4 . C5 . 117.82(14) yes C3 . C4 . C5 . 131.49(16) yes C4 . C5 . C6 . 121.05(14) yes C4 . C5 . C10 . 121.00(14) yes C6 . C5 . C10 . 117.93(14) yes C5 . C6 . C7 . 119.59(15) yes C5 . C6 . H161 . 120.767 no C7 . C6 . H161 . 119.589 no C6 . C7 . N1 . 122.71(14) yes C6 . C7 . C8 . 120.47(14) yes N1 . C7 . C8 . 116.80(14) yes C7 . C8 . H181 . 110.830 no C7 . C8 . H182 . 113.273 no H181 . C8 . H182 . 103.984 no C7 . C8 . H183 . 112.174 no H181 . C8 . H183 . 107.706 no H182 . C8 . H183 . 108.420 no C9 2_756 C9 . N1 . 116.48(16) yes C9 2_756 C9 . C10 . 120.56(16) yes N1 . C9 . C10 . 122.96(14) yes C5 . C10 . C9 . 118.96(14) yes C5 . C10 . H201 . 120.964 no C9 . C10 . H201 . 120.002 no