# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_stripcu _audit_creation_date 2013-08-21T15:06:50-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H20 Cu1 N1 O5 P2' _chemical_formula_sum 'C19 H20 Cu N O5 P2' _chemical_formula_weight 467.84 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _space_group_IT_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.6921(2) _cell_length_b 13.3051(5) _cell_length_c 13.9862(6) _cell_angle_alpha 64.365(4) _cell_angle_beta 80.711(3) _cell_angle_gamma 86.393(3) _cell_volume 942.42(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6736 _cell_measurement_theta_min 3.8624 _cell_measurement_theta_max 72.2622 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description parallelepiped _exptl_crystal_colour white _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.532 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.393 _exptl_absorpt_correction_T_max 0.838 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 8.1241 _diffrn_orient_matrix_ub_11 0.1163197463 _diffrn_orient_matrix_ub_12 -0.0259236254 _diffrn_orient_matrix_ub_13 -0.0941685315 _diffrn_orient_matrix_ub_21 0.0291587558 _diffrn_orient_matrix_ub_22 -0.1226169115 _diffrn_orient_matrix_ub_23 0.0787100895 _diffrn_orient_matrix_ub_31 -0.2466135853 _diffrn_orient_matrix_ub_32 -0.0279325445 _diffrn_orient_matrix_ub_33 -0.0144650299 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_unetI/netI 0.0816 _diffrn_reflns_number 17585 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.865 _diffrn_reflns_theta_max 72.375 _diffrn_reflns_theta_full 67.68 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_point_group_measured_fraction_ful 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.987 _reflns_number_total 3666 _reflns_number_gt 2506 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_hydrogens mixed #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0551P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3666 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.037 _refine_ls_shift/su_mean 0.006 _refine_diff_density_max 0.445 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.091 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.44425(9) 0.02729(4) 0.14008(4) 0.02089(15) Uani 1 d . . P1 P -0.07904(15) 0.10027(6) 0.22335(6) 0.01893(19) Uani 1 d . . P2 P 0.18548(15) 0.23064(6) -0.00114(6) 0.01881(19) Uani 1 d . . N1 N 0.4679(5) -0.1390(2) 0.2289(2) 0.0211(6) Uani 1 d . . O1 O 0.1164(4) 0.02105(16) 0.21279(16) 0.0217(5) Uani 1 d . . O2 O -0.3288(4) 0.06081(17) 0.23711(17) 0.0217(5) Uani 1 d . . O3 O 0.4165(4) 0.18511(16) 0.04191(17) 0.0229(5) Uani 1 d . . O4 O 0.0748(4) 0.17134(17) -0.05374(17) 0.0235(5) Uani 1 d . . O5 O 0.7148(5) 0.0215(2) 0.0336(2) 0.0239(5) Uani 1 d . . H5A H 0.797(7) -0.048(4) 0.054(3) 0.060(14) Uiso 1 d . . H5B H 0.808(8) 0.064(4) 0.012(4) 0.061(18) Uiso 1 d . . C1 C -0.0317(6) 0.2355(2) 0.1069(2) 0.0240(8) Uani 1 d . . H1A H -0.1851 0.2618 0.08 0.029 Uiso 1 calc . . H1B H 0.0223 0.2901 0.1295 0.029 Uiso 1 calc . . C11 C -0.0523(6) 0.1277(2) 0.3370(2) 0.0203(7) Uani 1 d . . C12 C 0.1507(6) 0.1769(3) 0.3427(3) 0.0259(8) Uani 1 d . . H12 H 0.2813 0.1957 0.2862 0.031 Uiso 1 calc . . C13 C 0.1634(7) 0.1985(3) 0.4304(3) 0.0300(8) Uani 1 d . . H13 H 0.3016 0.2331 0.4331 0.036 Uiso 1 calc . . C14 C -0.0244(7) 0.1699(3) 0.5137(3) 0.0317(8) Uani 1 d . . H14 H -0.0158 0.185 0.5735 0.038 Uiso 1 calc . . C15 C -0.2240(7) 0.1193(3) 0.5097(3) 0.0304(8) Uani 1 d . . H15 H -0.352 0.0982 0.5675 0.037 Uiso 1 calc . . C16 C -0.2389(6) 0.0990(3) 0.4209(2) 0.0249(7) Uani 1 d . . H16 H -0.3782 0.0652 0.4181 0.03 Uiso 1 calc . . C21 C 0.2418(6) 0.3743(2) -0.0949(3) 0.0229(7) Uani 1 d . . C22 C 0.4320(7) 0.4326(3) -0.0940(4) 0.0504(12) Uani 1 d . . H22 H 0.5385 0.3965 -0.0436 0.061 Uiso 1 calc . . C23 C 0.4694(8) 0.5432(3) -0.1656(4) 0.0643(15) Uani 1 d . . H23 H 0.6018 0.5822 -0.1638 0.077 Uiso 1 calc . . C24 C 0.3193(8) 0.5975(3) -0.2388(3) 0.0495(12) Uani 1 d . . H24 H 0.3472 0.6734 -0.2881 0.059 Uiso 1 calc . . C25 C 0.1268(9) 0.5404(3) -0.2399(3) 0.0542(12) Uani 1 d . . H25 H 0.0197 0.5771 -0.2898 0.065 Uiso 1 calc . . C26 C 0.0896(8) 0.4293(3) -0.1681(3) 0.0432(11) Uani 1 d . . H26 H -0.0434 0.3905 -0.1695 0.052 Uiso 1 calc . . C31 C 0.3032(7) -0.2113(3) 0.2370(3) 0.0308(8) Uani 1 d . . H31 H 0.1795 -0.1842 0.1941 0.037 Uiso 1 calc . . C32 C 0.3063(7) -0.3236(3) 0.3052(3) 0.0374(10) Uani 1 d . . H32 H 0.1866 -0.3719 0.308 0.045 Uiso 1 calc . . C33 C 0.4828(8) -0.3662(3) 0.3694(3) 0.0381(10) Uani 1 d . . C34 C 0.6556(8) -0.2912(3) 0.3584(3) 0.0397(10) Uani 1 d . . H34 H 0.7815 -0.3162 0.4001 0.048 Uiso 1 calc . . C35 C 0.6451(7) -0.1809(3) 0.2874(3) 0.0297(8) Uani 1 d . . H35 H 0.7693 -0.1321 0.2793 0.036 Uiso 1 calc . . C36 C 0.4879(12) -0.4879(3) 0.4473(3) 0.0699(16) Uani 1 d . . H36A H 0.3388 -0.5234 0.4488 0.084 Uiso 1 calc . . H36B H 0.6211 -0.5235 0.4187 0.084 Uiso 1 calc . . 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 0.0208(3) 0.0158(2) 0.0217(3) -0.00448(19) -0.0023(2) 0.00114(19) P1 0.0203(5) 0.0170(4) 0.0182(4) -0.0064(3) -0.0027(3) 0.0007(3) P2 0.0207(5) 0.0136(4) 0.0189(4) -0.0044(3) -0.0016(3) 0.0003(3) N1 0.0203(16) 0.0161(12) 0.0220(14) -0.0043(11) -0.0008(12) 0.0000(11) O1 0.0188(13) 0.0166(10) 0.0233(11) -0.0043(9) 0.0005(10) 0.0021(9) O2 0.0187(13) 0.0238(11) 0.0241(12) -0.0112(9) -0.0045(10) -0.0003(9) O3 0.0189(13) 0.0149(10) 0.0266(12) -0.0010(9) -0.0039(10) -0.0002(9) O4 0.0253(14) 0.0205(11) 0.0244(12) -0.0096(9) -0.0021(10) -0.0019(10) O5 0.0198(14) 0.0211(12) 0.0292(13) -0.0104(10) 0.0003(11) -0.0026(11) C1 0.031(2) 0.0151(15) 0.0209(16) -0.0042(13) -0.0008(15) 0.0021(14) C11 0.0207(18) 0.0170(15) 0.0227(16) -0.0074(13) -0.0063(14) 0.0029(13) C12 0.024(2) 0.0252(17) 0.0257(17) -0.0085(14) -0.0022(15) -0.0011(15) C13 0.030(2) 0.0283(18) 0.035(2) -0.0151(16) -0.0109(17) -0.0029(16) C14 0.043(2) 0.0301(18) 0.0285(19) -0.0160(16) -0.0136(17) 0.0056(17) C15 0.033(2) 0.037(2) 0.0209(17) -0.0131(15) -0.0023(16) 0.0029(17) C16 0.024(2) 0.0220(16) 0.0242(17) -0.0059(14) -0.0009(15) -0.0033(14) C21 0.024(2) 0.0140(14) 0.0244(17) -0.0045(13) 0.0011(14) 0.0012(14) C22 0.043(3) 0.026(2) 0.067(3) -0.001(2) -0.018(2) -0.0079(19) C23 0.041(3) 0.025(2) 0.101(4) -0.002(2) -0.006(3) -0.015(2) C24 0.053(3) 0.0180(18) 0.051(3) 0.0000(17) 0.018(2) 0.0048(19) C25 0.064(3) 0.036(2) 0.044(3) 0.001(2) -0.016(2) 0.015(2) C26 0.054(3) 0.0273(19) 0.042(2) -0.0046(18) -0.019(2) -0.0019(19) C31 0.036(2) 0.0295(18) 0.0263(18) -0.0092(15) -0.0118(16) -0.0015(16) C32 0.054(3) 0.0274(18) 0.0290(19) -0.0072(16) -0.0086(19) -0.0183(18) C33 0.068(3) 0.0180(17) 0.0248(19) -0.0022(15) -0.0152(19) -0.0076(18) C34 0.055(3) 0.0218(17) 0.042(2) -0.0063(16) -0.029(2) 0.0022(18) C35 0.037(2) 0.0168(16) 0.035(2) -0.0082(15) -0.0096(17) -0.0026(15) C36 0.148(5) 0.023(2) 0.034(2) 0.0019(18) -0.035(3) -0.021(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O3 1.963(2) . ? Cu1 O1 1.964(2) . ? Cu1 O5 1.985(2) . ? Cu1 N1 2.023(2) . ? Cu1 O2 2.207(2) 1_655 ? P1 O2 1.501(2) . ? P1 O1 1.518(2) . ? P1 C11 1.808(3) . ? P1 C1 1.829(3) . ? P2 O4 1.508(2) . ? P2 O3 1.516(2) . ? P2 C21 1.803(3) . ? P2 C1 1.813(3) . ? N1 C35 1.341(4) . ? N1 C31 1.343(4) . ? O2 Cu1 2.207(2) 1_455 ? O5 H5A 0.96(4) . ? O5 H5B 0.72(4) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C11 C16 1.382(4) . ? C11 C12 1.393(4) . ? C12 C13 1.389(5) . ? C12 H12 0.95 . ? C13 C14 1.382(5) . ? C13 H13 0.95 . ? C14 C15 1.377(5) . ? C14 H14 0.95 . ? C15 C16 1.397(5) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C21 C22 1.376(5) . ? C21 C26 1.375(5) . ? C22 C23 1.382(5) . ? C22 H22 0.95 . ? C23 C24 1.366(6) . ? C23 H23 0.95 . ? C24 C25 1.378(6) . ? C24 H24 0.95 . ? C25 C26 1.388(5) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? C31 C32 1.383(5) . ? C31 H31 0.95 . ? C32 C33 1.384(5) . ? C32 H32 0.95 . ? C33 C34 1.389(5) . ? C33 C36 1.512(5) . ? C34 C35 1.375(4) . ? C34 H34 0.95 . ? C35 H35 0.95 . ? C36 C36 1.395(8) 2_646 ? C36 H36A 0.99 . ? C36 H36B 0.99 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cu1 O1 92.38(9) . . ? O3 Cu1 O5 86.57(10) . . ? O1 Cu1 O5 159.86(10) . . ? O3 Cu1 N1 174.22(10) . . ? O1 Cu1 N1 88.77(10) . . ? O5 Cu1 N1 90.39(11) . . ? O3 Cu1 O2 94.21(9) . 1_655 ? O1 Cu1 O2 105.74(8) . 1_655 ? O5 Cu1 O2 94.40(9) . 1_655 ? N1 Cu1 O2 90.92(10) . 1_655 ? O2 P1 O1 115.62(12) . . ? O2 P1 C11 107.81(14) . . ? O1 P1 C11 109.15(14) . . ? O2 P1 C1 109.34(14) . . ? O1 P1 C1 109.33(13) . . ? C11 P1 C1 105.06(14) . . ? O4 P2 O3 117.74(13) . . ? O4 P2 C21 109.38(14) . . ? O3 P2 C21 106.72(14) . . ? O4 P2 C1 108.51(14) . . ? O3 P2 C1 108.70(14) . . ? C21 P2 C1 105.07(14) . . ? C35 N1 C31 117.0(3) . . ? C35 N1 Cu1 120.6(2) . . ? C31 N1 Cu1 122.4(2) . . ? P1 O1 Cu1 139.06(13) . . ? P1 O2 Cu1 137.30(13) . 1_455 ? P2 O3 Cu1 120.88(13) . . ? Cu1 O5 H5A 116(3) . . ? Cu1 O5 H5B 120(4) . . ? H5A O5 H5B 105(4) . . ? P2 C1 P1 113.00(16) . . ? P2 C1 H1A 109 . . ? P1 C1 H1A 109 . . ? P2 C1 H1B 109 . . ? P1 C1 H1B 109 . . ? H1A C1 H1B 107.8 . . ? C16 C11 C12 118.9(3) . . ? C16 C11 P1 119.1(3) . . ? C12 C11 P1 122.0(3) . . ? C13 C12 C11 120.5(3) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 119.8(3) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.2(3) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C11 C16 C15 120.5(3) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C22 C21 C26 118.3(3) . . ? C22 C21 P2 121.6(3) . . ? C26 C21 P2 120.1(3) . . ? C21 C22 C23 120.6(4) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 C23 C22 121.1(4) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C23 C24 C25 118.9(4) . . ? C23 C24 H24 120.6 . . ? C25 C24 H24 120.6 . . ? C24 C25 C26 120.0(4) . . ? C24 C25 H25 120 . . ? C26 C25 H25 120 . . ? C21 C26 C25 121.2(4) . . ? C21 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? N1 C31 C32 122.7(3) . . ? N1 C31 H31 118.7 . . ? C32 C31 H31 118.7 . . ? C31 C32 C33 120.4(3) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? C32 C33 C34 116.4(3) . . ? C32 C33 C36 121.9(4) . . ? C34 C33 C36 121.7(4) . . ? C35 C34 C33 120.3(3) . . ? C35 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? N1 C35 C34 123.1(3) . . ? N1 C35 H35 118.5 . . ? C34 C35 H35 118.5 . . ? C36 C36 C33 117.2(4) 2_646 . ? C36 C36 H36A 108 2_646 . ? C33 C36 H36A 108 . . ? C36 C36 H36B 108 2_646 . ? C33 C36 H36B 108 . . ? H36A C36 H36B 107.2 . . ? _database_code_depnum_ccdc_archive 'CCDC 957770' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_stripco _audit_creation_date 2013-10-03T21:28:13-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H20 Co1 N1 O5 P2' _chemical_formula_sum 'C19 H20 Co N O5 P2' _chemical_formula_weight 463.23 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _symmetry_Int_Tables_number 2 _cell_length_a 5.7631(3) _cell_length_b 13.0859(8) _cell_length_c 13.6759(7) _cell_angle_alpha 67.345(5) _cell_angle_beta 81.812(5) _cell_angle_gamma 89.757(5) _cell_volume 940.64(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2513 _cell_measurement_theta_min 3.8753 _cell_measurement_theta_max 28.8369 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description parallelepiped _exptl_crystal_colour purple _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.76057 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 16.4547 _diffrn_orient_matrix_ub_11 -0.007817005 _diffrn_orient_matrix_ub_12 -0.0404036796 _diffrn_orient_matrix_ub_13 0.0530105484 _diffrn_orient_matrix_ub_21 -0.0666905178 _diffrn_orient_matrix_ub_22 0.0356958564 _diffrn_orient_matrix_ub_23 0.0195419101 _diffrn_orient_matrix_ub_31 -0.1047006411 _diffrn_orient_matrix_ub_32 -0.0235154677 _diffrn_orient_matrix_ub_33 -0.0061755104 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_unetI/netI 0.1064 _diffrn_reflns_number 7559 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.881 _diffrn_reflns_theta_max 28.876 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.847 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.847 _diffrn_reflns_point_group_measured_fraction_ful 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.847 _reflns_number_total 4188 _reflns_number_gt 2482 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_hydrogens mixed #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0270P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4188 _refine_ls_number_parameters 259 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0891 _refine_ls_R_factor_gt 0.042 _refine_ls_wR_factor_ref 0.0746 _refine_ls_wR_factor_gt 0.0676 _refine_ls_goodness_of_fit_ref 0.84 _refine_ls_restrained_S_all 0.841 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.381 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.076 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.44024(8) 0.02537(3) 0.12597(3) 0.02335(13) Uani 1 d . . P1 P -0.08619(14) 0.10264(6) 0.20686(6) 0.0225(2) Uani 1 d . . P2 P 0.19265(15) 0.23483(6) -0.01192(6) 0.0226(2) Uani 1 d . . N1 N 0.4502(5) -0.14785(19) 0.22837(18) 0.0247(6) Uani 1 d . . O1 O 0.0991(3) 0.02397(14) 0.19633(15) 0.0253(5) Uani 1 d . . O2 O -0.3355(4) 0.06422(15) 0.21360(15) 0.0291(5) Uani 1 d . . O3 O 0.4171(4) 0.19138(15) 0.02870(15) 0.0279(5) Uani 1 d . . O4 O 0.0777(4) 0.17233(15) -0.06649(15) 0.0275(5) Uani 1 d . . O5 O 0.7161(4) 0.02011(15) 0.00832(16) 0.0245(5) Uani 1 d . . H5A H 0.797(5) -0.0405(17) 0.040(2) 0.029 Uiso 1 d . . H5B H 0.818(4) 0.0736(19) -0.014(2) 0.029 Uiso 1 d . . C1 C -0.0196(6) 0.2378(2) 0.0973(2) 0.0289(8) Uani 1 d . . H1A H -0.1636 0.2657 0.0701 0.035 Uiso 1 calc . . H1B H 0.0397 0.289 0.1249 0.035 Uiso 1 calc . . C11 C -0.0653(5) 0.1274(2) 0.3264(2) 0.0255(7) Uani 1 d . . C12 C 0.1415(6) 0.1729(3) 0.3381(3) 0.0370(9) Uani 1 d . . H12 H 0.2694 0.191 0.2836 0.044 Uiso 1 calc . . C13 C 0.1597(7) 0.1914(3) 0.4290(3) 0.0455(10) Uani 1 d . . H13 H 0.2985 0.2228 0.4352 0.055 Uiso 1 calc . . C14 C -0.0278(7) 0.1634(3) 0.5113(3) 0.0448(10) Uani 1 d . . H14 H -0.0159 0.1755 0.5731 0.054 Uiso 1 calc . . C15 C -0.2298(7) 0.1180(3) 0.5008(3) 0.0443(10) Uani 1 d . . H15 H -0.3559 0.0983 0.5564 0.053 Uiso 1 calc . . C16 C -0.2508(6) 0.1006(2) 0.4086(2) 0.0345(8) Uani 1 d . . H16 H -0.3912 0.0706 0.4023 0.041 Uiso 1 calc . . C21 C 0.2484(6) 0.3784(2) -0.1019(2) 0.0285(8) Uani 1 d . . C22 C 0.0991(8) 0.4304(3) -0.1712(3) 0.0573(12) Uani 1 d . . H22 H -0.0333 0.3911 -0.173 0.069 Uiso 1 calc . . C23 C 0.1396(9) 0.5415(3) -0.2399(3) 0.0703(14) Uani 1 d . . H23 H 0.0345 0.5762 -0.2866 0.084 Uiso 1 calc . . C24 C 0.3316(9) 0.5982(3) -0.2382(4) 0.0725(15) Uani 1 d . . H24 H 0.3601 0.6724 -0.2839 0.087 Uiso 1 calc . . C25 C 0.4823(9) 0.5478(4) -0.1708(5) 0.112(2) Uani 1 d . . H25 H 0.6152 0.5873 -0.1699 0.134 Uiso 1 calc . . C26 C 0.4420(7) 0.4378(3) -0.1026(4) 0.0781(16) Uani 1 d . . H26 H 0.5486 0.4038 -0.0564 0.094 Uiso 1 calc . . C31 C 0.6218(6) -0.1848(2) 0.2865(2) 0.0333(9) Uani 1 d . . H31 H 0.7496 -0.1363 0.2753 0.04 Uiso 1 calc . . C32 C 0.6204(6) -0.2908(3) 0.3624(3) 0.0404(9) Uani 1 d . . H32 H 0.7447 -0.312 0.4011 0.049 Uiso 1 calc . . C33 C 0.4354(6) -0.3659(3) 0.3813(2) 0.0350(9) Uani 1 d . . C34 C 0.2626(6) -0.3280(3) 0.3187(3) 0.0396(10) Uani 1 d . . H34 H 0.1357 -0.3757 0.3268 0.048 Uiso 1 calc . . C35 C 0.2733(6) -0.2208(3) 0.2441(2) 0.0346(9) Uani 1 d . . H35 H 0.1528 -0.1983 0.2032 0.041 Uiso 1 calc . . C36 C 0.4159(8) -0.4830(3) 0.4637(3) 0.0654(14) Uani 1 d . . H36A H 0.2613 -0.4951 0.5064 0.078 Uiso 1 calc . . H36B H 0.4222 -0.5324 0.4258 0.078 Uiso 1 calc . . 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 Co1 0.0192(3) 0.0222(2) 0.0247(2) -0.00496(19) -0.00262(19) 0.00228(17) P1 0.0213(5) 0.0226(4) 0.0222(4) -0.0075(4) -0.0027(4) 0.0024(3) P2 0.0236(5) 0.0188(4) 0.0227(4) -0.0050(4) -0.0035(4) 0.0013(3) N1 0.0252(16) 0.0243(14) 0.0202(13) -0.0039(12) -0.0034(12) 0.0006(11) O1 0.0236(13) 0.0206(11) 0.0266(11) -0.0064(9) 0.0044(9) 0.0033(8) O2 0.0221(13) 0.0322(12) 0.0311(12) -0.0097(10) -0.0052(10) 0.0006(9) O3 0.0231(13) 0.0232(11) 0.0323(12) -0.0049(10) -0.0049(10) 0.0006(9) O4 0.0311(14) 0.0248(11) 0.0258(11) -0.0088(10) -0.0053(10) 0.0006(9) O5 0.0170(13) 0.0216(12) 0.0302(12) -0.0058(10) -0.0015(10) -0.0008(9) C1 0.036(2) 0.0245(17) 0.0250(16) -0.0089(15) -0.0030(15) 0.0052(14) C11 0.0224(19) 0.0260(16) 0.0263(16) -0.0087(14) -0.0017(14) 0.0010(13) C12 0.028(2) 0.047(2) 0.036(2) -0.0167(18) -0.0007(17) -0.0034(16) C13 0.039(2) 0.056(2) 0.048(2) -0.025(2) -0.013(2) -0.0040(18) C14 0.058(3) 0.053(2) 0.033(2) -0.0241(19) -0.014(2) 0.0065(19) C15 0.042(3) 0.057(2) 0.036(2) -0.023(2) 0.0041(18) -0.0042(19) C16 0.031(2) 0.0378(19) 0.0348(19) -0.0157(16) 0.0009(16) -0.0073(15) C21 0.029(2) 0.0229(17) 0.0269(17) -0.0039(15) 0.0006(15) 0.0021(14) C22 0.078(3) 0.034(2) 0.055(2) -0.003(2) -0.035(2) 0.001(2) C23 0.097(4) 0.038(2) 0.061(3) 0.004(2) -0.032(3) 0.016(2) C24 0.073(4) 0.025(2) 0.079(3) 0.010(2) 0.029(3) 0.004(2) C25 0.063(4) 0.038(3) 0.184(6) 0.015(3) -0.026(4) -0.019(2) C26 0.049(3) 0.037(2) 0.118(4) 0.011(3) -0.034(3) -0.009(2) C31 0.030(2) 0.0274(18) 0.038(2) -0.0061(16) -0.0133(17) 0.0006(14) C32 0.041(2) 0.0322(19) 0.045(2) -0.0055(17) -0.0272(18) 0.0058(16) C33 0.045(2) 0.0280(18) 0.0291(18) -0.0065(16) -0.0082(17) -0.0024(16) C34 0.039(2) 0.0333(19) 0.042(2) -0.0053(17) -0.0177(18) -0.0104(16) C35 0.038(2) 0.0339(19) 0.0290(18) -0.0061(16) -0.0133(16) -0.0046(16) C36 0.082(4) 0.033(2) 0.063(3) 0.009(2) -0.035(2) -0.014(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.059(2) . ? Co1 O2 2.0690(19) 1_655 ? Co1 O3 2.0805(18) . ? Co1 O5 2.116(2) . ? Co1 N1 2.163(2) . ? Co1 O5 2.420(2) 2_655 ? P1 O2 1.503(2) . ? P1 O1 1.510(2) . ? P1 C11 1.804(3) . ? P1 C1 1.823(3) . ? P2 O3 1.503(2) . ? P2 O4 1.510(2) . ? P2 C1 1.803(3) . ? P2 C21 1.805(3) . ? N1 C31 1.330(4) . ? N1 C35 1.336(3) . ? O2 Co1 2.0690(19) 1_455 ? O5 H5A 0.907(17) . ? O5 H5B 0.845(16) . ? C1 H1A 0.97 . ? C1 H1B 0.97 . ? C11 C16 1.374(4) . ? C11 C12 1.391(4) . ? C12 C13 1.372(4) . ? C12 H12 0.93 . ? C13 C14 1.381(5) . ? C13 H13 0.93 . ? C14 C15 1.360(4) . ? C14 H14 0.93 . ? C15 C16 1.386(4) . ? C15 H15 0.93 . ? C16 H16 0.93 . ? C21 C22 1.354(4) . ? C21 C26 1.359(4) . ? C22 C23 1.392(4) . ? C22 H22 0.93 . ? C23 C24 1.343(6) . ? C23 H23 0.93 . ? C24 C25 1.339(6) . ? C24 H24 0.93 . ? C25 C26 1.380(5) . ? C25 H25 0.93 . ? C26 H26 0.93 . ? C31 C32 1.374(4) . ? C31 H31 0.93 . ? C32 C33 1.379(4) . ? C32 H32 0.93 . ? C33 C34 1.372(4) . ? C33 C36 1.506(4) . ? C34 C35 1.375(4) . ? C34 H34 0.93 . ? C35 H35 0.93 . ? C36 C36 1.432(7) 2_646 ? C36 H36A 0.97 . ? C36 H36B 0.97 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O2 108.90(8) . 1_655 ? O1 Co1 O3 88.75(8) . . ? O2 Co1 O3 92.35(7) 1_655 . ? O1 Co1 O5 157.26(8) . . ? O2 Co1 O5 93.63(8) 1_655 . ? O3 Co1 O5 87.25(8) . . ? O1 Co1 N1 89.22(9) . . ? O2 Co1 N1 88.93(8) 1_655 . ? O3 Co1 N1 177.86(10) . . ? O5 Co1 N1 94.38(9) . . ? O1 Co1 O5 87.66(8) . 2_655 ? O2 Co1 O5 163.43(8) 1_655 2_655 ? O3 Co1 O5 87.31(7) . 2_655 ? O5 Co1 O5 69.81(9) . 2_655 ? N1 Co1 O5 91.95(8) . 2_655 ? O2 P1 O1 115.88(12) . . ? O2 P1 C11 107.73(13) . . ? O1 P1 C11 108.38(14) . . ? O2 P1 C1 109.75(13) . . ? O1 P1 C1 109.72(13) . . ? C11 P1 C1 104.77(13) . . ? O3 P2 O4 116.42(12) . . ? O3 P2 C1 109.66(13) . . ? O4 P2 C1 107.63(13) . . ? O3 P2 C21 108.41(13) . . ? O4 P2 C21 109.45(13) . . ? C1 P2 C21 104.63(14) . . ? C31 N1 C35 116.6(2) . . ? C31 N1 Co1 121.57(19) . . ? C35 N1 Co1 121.6(2) . . ? P1 O1 Co1 140.63(11) . . ? P1 O2 Co1 142.00(13) . 1_455 ? P2 O3 Co1 121.50(11) . . ? Co1 O5 H5A 107.1(19) . . ? Co1 O5 H5B 115(2) . . ? H5A O5 H5B 104(3) . . ? P2 C1 P1 113.49(17) . . ? P2 C1 H1A 108.9 . . ? P1 C1 H1A 108.9 . . ? P2 C1 H1B 108.9 . . ? P1 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C16 C11 C12 118.2(3) . . ? C16 C11 P1 121.2(2) . . ? C12 C11 P1 120.6(2) . . ? C13 C12 C11 121.0(3) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 120.1(3) . . ? C12 C13 H13 120 . . ? C14 C13 H13 120 . . ? C15 C14 C13 119.3(3) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C16 121.0(3) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C11 C16 C15 120.4(3) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C22 C21 C26 117.8(3) . . ? C22 C21 P2 121.1(3) . . ? C26 C21 P2 121.1(3) . . ? C21 C22 C23 121.4(4) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C24 C23 C22 119.4(4) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C25 C24 C23 120.0(4) . . ? C25 C24 H24 120 . . ? C23 C24 H24 120 . . ? C24 C25 C26 120.6(4) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C21 C26 C25 120.8(4) . . ? C21 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? N1 C31 C32 123.5(3) . . ? N1 C31 H31 118.2 . . ? C32 C31 H31 118.2 . . ? C31 C32 C33 120.3(3) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? C34 C33 C32 115.7(3) . . ? C34 C33 C36 120.0(3) . . ? C32 C33 C36 124.3(3) . . ? C33 C34 C35 121.3(3) . . ? C33 C34 H34 119.3 . . ? C35 C34 H34 119.3 . . ? N1 C35 C34 122.5(3) . . ? N1 C35 H35 118.8 . . ? C34 C35 H35 118.8 . . ? C36 C36 C33 119.0(4) 2_646 . ? C36 C36 H36A 107.6 2_646 . ? C33 C36 H36A 107.6 . . ? C36 C36 H36B 107.6 2_646 . ? C33 C36 H36B 107.6 . . ? H36A C36 H36B 107 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5B O4 0.845(16) 1.850(18) 2.686(3) 170(3) 1_655 O5 H5A O4 0.907(17) 1.792(19) 2.662(3) 160(3) 2_655 # END of CIF _database_code_depnum_ccdc_archive 'CCDC 957771'