# Electronic Supplementary Material (ESI) for Chemical Communications # 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_cuedpba2 _iucr_refine_instructions_details ; TITL cuedpba_2 CELL 0.71073 8.8221 11.5730 13.5452 68.274 86.530 82.154 ZERR 1.00 0.0002 0.0003 0.0003 0.002 0.002 0.002 LATT 1 SFAC C H N O CU UNIT 44 52 4 16 2 MERG 2 DFIX 1 H8a O8 DFIX -2 H8a H7a DFIX -2.2 H7a H8a DANG 2.2 0.01 H8A C23 EADP O8 C23 C24 SHEL 999 0.8 DFIX 0.800 0.001 O7 H7A FMAP 2 PLAN 15 ACTA BOND BOND $H L.S. 25 TEMP -153.00 WGHT 0.162500 4.446900 FVAR 5.45136 0.68457 CU1 5 0.363482 0.112783 0.011836 11.00000 0.01166 0.04243 = 0.01256 -0.00617 0.00070 -0.00789 O2 4 0.269185 -0.020483 0.129262 11.00000 0.01034 0.04056 = 0.01567 -0.00721 -0.00011 -0.00532 O4 4 0.568731 0.036435 0.069359 11.00000 0.01289 0.04604 = 0.01547 -0.01287 0.00187 -0.00773 O1 4 0.153199 0.177222 -0.032587 11.00000 0.01598 0.04350 = 0.01619 -0.00262 -0.00204 -0.00890 O6 4 0.713009 -0.026920 0.214461 11.00000 0.01311 0.04980 = 0.01780 -0.01280 0.00016 -0.00039 O5 4 0.389573 0.193400 0.150943 11.00000 0.02134 0.04085 = 0.01769 -0.00711 -0.00414 -0.00050 N1 3 0.030682 -0.064996 0.192269 11.00000 0.00994 0.03284 = 0.01657 -0.00663 -0.00119 -0.00363 AFIX 43 H1 2 -0.067877 -0.039111 0.183828 11.00000 -1.20000 AFIX 0 O3 4 -0.084705 0.131571 0.021283 11.00000 0.01271 0.04610 = 0.02618 -0.00158 -0.00445 -0.00449 N2 3 0.505958 0.085744 0.309924 11.00000 0.01622 0.03264 = 0.01470 -0.00867 -0.00214 0.00049 AFIX 43 H2 2 0.579834 0.026178 0.341269 11.00000 -1.20000 AFIX 0 C2 1 0.125988 0.001091 0.123046 11.00000 0.01448 0.03506 = 0.01461 -0.00969 -0.00043 -0.00492 C17 1 0.487157 0.115260 0.205595 11.00000 0.01401 0.03335 = 0.01479 -0.00791 0.00111 -0.00775 C3 1 0.077828 -0.176920 0.280846 11.00000 0.01160 0.02990 = 0.01670 -0.00895 0.00225 -0.00387 C4 1 0.150333 -0.171398 0.367982 11.00000 0.01497 0.02687 = 0.01777 -0.00967 0.00138 -0.00449 C16 1 0.415964 0.143079 0.373929 11.00000 0.01619 0.02747 = 0.01607 -0.00754 -0.00480 0.00001 C11 1 0.313725 0.075458 0.449063 11.00000 0.01649 0.02397 = 0.01543 -0.00628 -0.00516 -0.00017 C9 1 0.177791 -0.045571 0.369959 11.00000 0.01877 0.02380 = 0.01865 -0.00669 -0.00308 -0.00384 AFIX 23 H9A 2 0.078012 0.000563 0.378741 11.00000 -1.20000 H9B 2 0.221585 0.003737 0.300432 11.00000 -1.20000 AFIX 0 C18 1 0.602253 0.033453 0.160122 11.00000 0.01076 0.03769 = 0.01478 -0.00817 0.00299 -0.00813 C8 1 0.045508 -0.289458 0.277827 11.00000 0.01964 0.03420 = 0.02616 -0.01677 0.00021 -0.00360 AFIX 43 H8 2 -0.004232 -0.290749 0.218035 11.00000 -1.20000 AFIX 0 C10 1 0.284675 -0.053681 0.457878 11.00000 0.02265 0.02544 = 0.01808 -0.00886 -0.00317 -0.00363 AFIX 23 H10A 2 0.238083 -0.096727 0.528124 11.00000 -1.20000 H10B 2 0.383073 -0.103641 0.452431 11.00000 -1.20000 AFIX 0 C15 1 0.436029 0.264015 0.363427 11.00000 0.02216 0.02771 = 0.02293 -0.00460 -0.00092 -0.00377 AFIX 43 H15 2 0.503986 0.309348 0.310616 11.00000 -1.20000 AFIX 0 C5 1 0.190859 -0.283947 0.450655 11.00000 0.02334 0.02806 = 0.02117 -0.00994 -0.00379 -0.00070 AFIX 43 H5 2 0.241725 -0.283567 0.510360 11.00000 -1.20000 AFIX 0 C1 1 0.054773 0.114076 0.028970 11.00000 0.01582 0.03798 = 0.01570 -0.00634 -0.00241 -0.00507 C12 1 0.235217 0.131825 0.515532 11.00000 0.01998 0.03030 = 0.02162 -0.01016 0.00234 -0.00175 AFIX 43 H12 2 0.165775 0.087448 0.567645 11.00000 -1.20000 AFIX 0 C13 1 0.257542 0.252693 0.506337 11.00000 0.02677 0.03114 = 0.03060 -0.01601 0.00423 0.00073 AFIX 43 H13 2 0.204375 0.289573 0.552594 11.00000 -1.20000 AFIX 0 C14 1 0.357189 0.318648 0.429771 11.00000 0.03200 0.02402 = 0.03682 -0.01179 0.00127 -0.00355 AFIX 43 H14 2 0.371411 0.401229 0.422794 11.00000 -1.20000 AFIX 0 C6 1 0.159301 -0.396596 0.448584 11.00000 0.03377 0.02204 = 0.02832 -0.00646 -0.00440 0.00161 AFIX 43 H6 2 0.188111 -0.472096 0.506731 11.00000 -1.20000 AFIX 0 C7 1 0.086337 -0.400570 0.362891 11.00000 0.03252 0.02806 = 0.03578 -0.01723 -0.00008 -0.00551 AFIX 43 H7 2 0.064204 -0.478206 0.361923 11.00000 -1.20000 AFIX 0 O7 4 0.441334 0.253714 -0.100767 11.00000 0.02021 0.04275 = 0.01838 -0.00189 -0.00078 -0.00987 PART 1 C21A 1 0.437762 0.269042 -0.210674 21.00000 0.03375 0.03566 = 0.01912 -0.00283 0.00428 -0.00610 AFIX 23 H21A 2 0.344809 0.238125 -0.224121 21.00000 -1.20000 H21B 2 0.528161 0.218782 -0.227900 21.00000 -1.20000 AFIX 0 C22A 1 0.437777 0.402558 -0.279637 21.00000 0.07680 0.04414 = 0.03107 0.00863 -0.01284 -0.02273 AFIX 137 H22A 2 0.445429 0.410280 -0.354247 21.00000 -1.50000 H22B 2 0.525279 0.434994 -0.262116 21.00000 -1.50000 H22C 2 0.342633 0.450783 -0.268199 21.00000 -1.50000 AFIX 0 PART 2 C21B 1 0.379167 0.337113 -0.204947 -21.00000 0.03106 0.06023 = 0.03985 0.01961 -0.01467 -0.01222 AFIX 23 H21C 2 0.277467 0.314006 -0.211953 -21.00000 -1.20000 H21D 2 0.363362 0.423914 -0.206007 -21.00000 -1.20000 AFIX 0 C22B 1 0.461801 0.336291 -0.287666 -21.00000 0.10996 0.09391 = 0.02755 -0.00214 -0.01227 -0.04262 AFIX 137 H22D 2 0.448989 0.420045 -0.343355 -21.00000 -1.50000 H22E 2 0.428898 0.275737 -0.314271 -21.00000 -1.50000 H22F 2 0.569734 0.312471 -0.267656 -21.00000 -1.50000 AFIX 0 PART -1 O8 4 0.694646 0.321861 -0.067352 11.00000 0.04991 0.05957 = 0.16776 -0.02974 -0.03308 -0.00250 PART 0 C24 1 0.773417 0.562377 -0.147896 11.00000 0.04991 0.05957 = 0.16776 -0.02974 -0.03308 -0.00250 AFIX 137 H24A 2 0.752252 0.580094 -0.222630 11.00000 -1.50000 H24C 2 0.883904 0.556241 -0.138583 11.00000 -1.50000 H24B 2 0.720913 0.630175 -0.126948 11.00000 -1.50000 AFIX 0 C23 1 0.715108 0.436656 -0.077461 11.00000 0.04991 0.05957 = 0.16776 -0.02974 -0.03308 -0.00250 AFIX 23 H23B 2 0.772219 0.418107 -0.011547 11.00000 -1.20000 H23A 2 0.610059 0.468067 -0.061450 11.00000 -1.20000 AFIX 0 H7A 2 0.492821 0.290465 -0.078693 11.00000 -1.20000 H8A 2 0.741310 0.253738 -0.094515 11.00000 -1.20000 HKLF 4 REM cuedpba_2 REM R1 = 0.0759 for 4891 Fo > 4sig(Fo) and 0.0783 for all 5199 data REM 314 parameters refined using 4 restraints END WGHT 0.1622 4.4705 REM Highest difference peak 2.730, deepest hole -1.820, 1-sigma level 0.183 Q1 1 1.0074 0.6772 -0.2499 11.00000 0.05 2.73 Q2 1 0.7142 0.3351 0.1695 11.00000 0.05 2.61 Q3 1 1.0471 0.7378 -0.2085 11.00000 0.05 1.79 ; # start Validation Reply Form _vrf_PLAT220_ALERT_2_B_cuedpba2 ; PROBLEM: Large Non-Solvent 4.1 Ratio RESPONSE: A continuous negative density was found in a large void (Platon - Total Potential Solvent Area Vol 169.6 Ang\\\^3 ,p er Unit Cell Vol 1272.6 Ang\\\^3 [13.3%]). Disorder model was used for modelling Etanhol molecules attached to the Cu tom, however no solvent molecules was modeled within the void. ; # end Validation Reply Form #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C44 H52 Cu2 N4 O16' _chemical_formula_weight 1019.98 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_space_group_name_hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_cell_setting triclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8221(2) _cell_length_b 11.5730(3) _cell_length_c 13.5452(3) _cell_angle_alpha 68.274(2) _cell_angle_beta 86.530(2) _cell_angle_gamma 82.154(2) _cell_volume 1272.60(5) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 18527 _cell_measurement_theta_min 2.8184 _cell_measurement_theta_max 31.0505 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description parallelepiped _exptl_crystal_colour 'light blue' _exptl_crystal_size_max 0.5532 _exptl_crystal_size_mid 0.2403 _exptl_crystal_size_min 0.1168 _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 530 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.903 _exptl_absorpt_correction_T_min 0.705 _exptl_absorpt_correction_T_max 0.902 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator mirror _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_unetI/netI 0.0171 _diffrn_reflns_number 30924 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 5199 _reflns_number_gt 4891 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_method 'w scans' _diffrn_standards_number 5199 #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_data_collection '(Agilent Technologies, 2012)' _computing_cell_refinement '(Agilent Technologies, 2012)' _computing_data_reduction '(Agilent Technologies, 2012)' _computing_publication_material 'PublCIF (Westrip, 2010)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1623P)^2^+4.4737P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5199 _refine_ls_number_parameters 314 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.2474 _refine_ls_wR_factor_gt 0.2447 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.73 _refine_diff_density_min -1.821 _refine_diff_density_rms 0.183 #----------------------------------------------------------------------------# # 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' Cu Cu 0.3201 1.2651 '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.36348(5) 0.11278(5) 0.01184(4) 0.0229(2) Uani 1 1 d . . . O2 O 0.2692(3) -0.0205(3) 0.1293(2) 0.0229(6) Uani 1 1 d . . . O4 O 0.5687(3) 0.0364(3) 0.0694(2) 0.0240(6) Uani 1 1 d . . . O1 O 0.1532(4) 0.1772(3) -0.0326(2) 0.0270(7) Uani 1 1 d . . . O6 O 0.7130(3) -0.0269(3) 0.2145(2) 0.0271(7) Uani 1 1 d . . . O5 O 0.3896(4) 0.1934(3) 0.1509(2) 0.0278(7) Uani 1 1 d . . . N1 N 0.0307(4) -0.0650(3) 0.1923(3) 0.0203(7) Uani 1 1 d . . . H1 H -0.0679 -0.0391 0.1838 0.024 Uiso 1 1 calc R . . O3 O -0.0847(4) 0.1316(3) 0.0213(3) 0.0314(8) Uani 1 1 d . . . N2 N 0.5060(4) 0.0857(3) 0.3099(3) 0.0214(7) Uani 1 1 d . . . H2 H 0.5798 0.0262 0.3413 0.026 Uiso 1 1 calc R . . C2 C 0.1260(5) 0.0011(4) 0.1230(3) 0.0210(8) Uani 1 1 d . . . C17 C 0.4872(4) 0.1153(4) 0.2056(3) 0.0206(8) Uani 1 1 d . . . C3 C 0.0778(4) -0.1769(4) 0.2808(3) 0.0193(8) Uani 1 1 d . . . C4 C 0.1503(4) -0.1714(4) 0.3680(3) 0.0193(8) Uani 1 1 d . . . C16 C 0.4160(5) 0.1431(4) 0.3739(3) 0.0201(8) Uani 1 1 d . . . C11 C 0.3137(5) 0.0755(4) 0.4491(3) 0.0189(8) Uani 1 1 d . . . C9 C 0.1778(5) -0.0456(4) 0.3700(3) 0.0205(8) Uani 1 1 d . . . H9A H 0.0780 0.0006 0.3787 0.025 Uiso 1 1 calc R . . H9B H 0.2216 0.0037 0.3004 0.025 Uiso 1 1 calc R . . C18 C 0.6023(4) 0.0335(4) 0.1601(3) 0.0211(8) Uani 1 1 d . . . C8 C 0.0455(5) -0.2895(4) 0.2778(4) 0.0250(9) Uani 1 1 d . . . H8 H -0.0042 -0.2907 0.2180 0.030 Uiso 1 1 calc R . . C10 C 0.2847(5) -0.0537(4) 0.4579(3) 0.0216(8) Uani 1 1 d . . . H10A H 0.2381 -0.0967 0.5281 0.026 Uiso 1 1 calc R . . H10B H 0.3831 -0.1036 0.4524 0.026 Uiso 1 1 calc R . . C15 C 0.4360(5) 0.2640(4) 0.3634(4) 0.0255(9) Uani 1 1 d . . . H15 H 0.5040 0.3093 0.3106 0.031 Uiso 1 1 calc R . . C5 C 0.1909(5) -0.2839(4) 0.4507(3) 0.0240(9) Uani 1 1 d . . . H5 H 0.2417 -0.2836 0.5104 0.029 Uiso 1 1 calc R . . C1 C 0.0548(5) 0.1141(4) 0.0290(3) 0.0239(9) Uani 1 1 d . . . C12 C 0.2352(5) 0.1318(4) 0.5155(3) 0.0240(9) Uani 1 1 d . . . H12 H 0.1658 0.0874 0.5676 0.029 Uiso 1 1 calc R . . C13 C 0.2575(5) 0.2527(4) 0.5063(4) 0.0288(10) Uani 1 1 d . . . H13 H 0.2044 0.2896 0.5526 0.035 Uiso 1 1 calc R . . C14 C 0.3572(6) 0.3186(4) 0.4298(4) 0.0308(10) Uani 1 1 d . . . H14 H 0.3714 0.4012 0.4228 0.037 Uiso 1 1 calc R . . C6 C 0.1593(6) -0.3966(4) 0.4486(4) 0.0292(10) Uani 1 1 d . . . H6 H 0.1881 -0.4721 0.5067 0.035 Uiso 1 1 calc R . . C7 C 0.0863(6) -0.4006(4) 0.3629(4) 0.0304(10) Uani 1 1 d . . . H7 H 0.0642 -0.4782 0.3619 0.036 Uiso 1 1 calc R . . O7 O 0.4413(4) 0.2537(3) -0.1008(3) 0.0292(7) Uani 1 1 d D . . C21A C 0.4378(12) 0.2690(10) -0.2107(6) 0.032(3) Uani 0.68(3) 1 d P A 1 H21A H 0.3448 0.2381 -0.2241 0.038 Uiso 0.68(3) 1 calc PR A 1 H21B H 0.5282 0.2188 -0.2279 0.038 Uiso 0.68(3) 1 calc PR A 1 C22A C 0.4378(16) 0.4026(13) -0.2796(10) 0.055(3) Uani 0.68(3) 1 d P A 1 H22A H 0.4454 0.4103 -0.3542 0.083 Uiso 0.68(3) 1 calc PR A 1 H22B H 0.5253 0.4350 -0.2621 0.083 Uiso 0.68(3) 1 calc PR A 1 H22C H 0.3426 0.4508 -0.2682 0.083 Uiso 0.68(3) 1 calc PR A 1 C21B C 0.379(3) 0.337(3) -0.2049(18) 0.053(9) Uani 0.32(3) 1 d P A 2 H21C H 0.2775 0.3140 -0.2120 0.064 Uiso 0.32(3) 1 calc PR A 2 H21D H 0.3634 0.4239 -0.2060 0.064 Uiso 0.32(3) 1 calc PR A 2 C22B C 0.462(5) 0.336(5) -0.288(2) 0.079(12) Uani 0.32(3) 1 d P A 2 H22D H 0.4490 0.4200 -0.3434 0.119 Uiso 0.32(3) 1 calc PR A 2 H22E H 0.4289 0.2757 -0.3143 0.119 Uiso 0.32(3) 1 calc PR A 2 H22F H 0.5697 0.3125 -0.2677 0.119 Uiso 0.32(3) 1 calc PR A 2 O8 O 0.6946(7) 0.3219(6) -0.0674(7) 0.0949(18) Uani 1 1 d D B -1 C24 C 0.7734(10) 0.5624(8) -0.1479(11) 0.0949(18) Uani 1 1 d . B . H24A H 0.7523 0.5801 -0.2226 0.142 Uiso 1 1 calc R . . H24C H 0.8839 0.5562 -0.1386 0.142 Uiso 1 1 calc R . . H24B H 0.7209 0.6302 -0.1269 0.142 Uiso 1 1 calc R . . C23 C 0.7151(10) 0.4367(8) -0.0775(11) 0.0949(18) Uani 1 1 d D . . H23B H 0.7722 0.4181 -0.0115 0.114 Uiso 1 1 calc R B . H23A H 0.6101 0.4681 -0.0615 0.114 Uiso 1 1 calc R . . H7A H 0.493(7) 0.290(9) -0.079(9) 0.114 Uiso 1 1 d D . . H8A H 0.741(8) 0.254(4) -0.095(7) 0.114 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0117(3) 0.0424(4) 0.0126(3) -0.0062(2) 0.0007(2) -0.0079(2) O2 0.0103(13) 0.0406(17) 0.0157(14) -0.0072(12) -0.0001(10) -0.0053(12) O4 0.0129(14) 0.0460(18) 0.0155(14) -0.0129(13) 0.0019(11) -0.0077(12) O1 0.0160(14) 0.0435(18) 0.0162(14) -0.0026(13) -0.0020(11) -0.0089(13) O6 0.0131(14) 0.0498(19) 0.0178(15) -0.0128(13) 0.0002(11) -0.0004(13) O5 0.0213(15) 0.0409(18) 0.0177(15) -0.0071(13) -0.0041(12) -0.0005(13) N1 0.0099(15) 0.0328(18) 0.0166(16) -0.0066(14) -0.0012(12) -0.0036(13) O3 0.0127(15) 0.0461(19) 0.0262(17) -0.0016(14) -0.0044(12) -0.0045(13) N2 0.0162(16) 0.0326(18) 0.0147(16) -0.0087(14) -0.0021(13) 0.0005(13) C2 0.0145(18) 0.035(2) 0.0146(18) -0.0097(16) -0.0004(14) -0.0049(16) C17 0.0140(18) 0.033(2) 0.0148(18) -0.0079(16) 0.0011(14) -0.0077(16) C3 0.0116(17) 0.030(2) 0.0167(19) -0.0090(16) 0.0022(14) -0.0039(14) C4 0.0150(18) 0.027(2) 0.0178(19) -0.0097(16) 0.0014(15) -0.0045(15) C16 0.0162(18) 0.027(2) 0.0161(19) -0.0075(15) -0.0048(15) 0.0000(15) C11 0.0165(18) 0.0240(19) 0.0154(18) -0.0063(15) -0.0052(14) -0.0002(14) C9 0.0188(19) 0.0238(19) 0.0186(19) -0.0067(15) -0.0031(15) -0.0038(15) C18 0.0108(18) 0.038(2) 0.0148(18) -0.0082(16) 0.0030(14) -0.0081(16) C8 0.020(2) 0.034(2) 0.026(2) -0.0168(18) 0.0002(16) -0.0036(16) C10 0.023(2) 0.025(2) 0.0181(19) -0.0089(15) -0.0032(16) -0.0036(15) C15 0.022(2) 0.028(2) 0.023(2) -0.0046(17) -0.0009(16) -0.0038(16) C5 0.023(2) 0.028(2) 0.021(2) -0.0099(17) -0.0038(16) -0.0007(16) C1 0.016(2) 0.038(2) 0.0157(19) -0.0063(17) -0.0024(15) -0.0051(17) C12 0.020(2) 0.030(2) 0.022(2) -0.0102(17) 0.0023(16) -0.0018(16) C13 0.027(2) 0.031(2) 0.031(2) -0.0160(19) 0.0042(18) 0.0007(18) C14 0.032(2) 0.024(2) 0.037(3) -0.0118(19) 0.001(2) -0.0036(18) C6 0.034(2) 0.022(2) 0.028(2) -0.0065(17) -0.0044(19) 0.0016(18) C7 0.033(2) 0.028(2) 0.036(3) -0.0172(19) 0.000(2) -0.0055(18) O7 0.0202(15) 0.0428(18) 0.0184(16) -0.0019(13) -0.0008(12) -0.0099(13) C21A 0.034(5) 0.036(5) 0.019(4) -0.003(3) 0.004(3) -0.006(4) C22A 0.077(8) 0.044(6) 0.031(5) 0.009(5) -0.013(5) -0.023(6) C21B 0.031(11) 0.060(17) 0.040(11) 0.020(11) -0.015(9) -0.012(12) C22B 0.11(3) 0.09(3) 0.028(13) -0.002(16) -0.012(13) -0.04(2) O8 0.050(2) 0.060(2) 0.168(5) -0.030(3) -0.033(3) -0.0025(18) C24 0.050(2) 0.060(2) 0.168(5) -0.030(3) -0.033(3) -0.0025(18) C23 0.050(2) 0.060(2) 0.168(5) -0.030(3) -0.033(3) -0.0025(18) _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 O1 1.945(3) . ? Cu1 O7 1.948(3) . ? Cu1 O4 1.973(3) . ? Cu1 O2 1.994(3) . ? Cu1 O4 2.365(3) 2_655 ? Cu1 O5 2.426(3) . ? O2 C2 1.256(5) . ? O4 C18 1.269(5) . ? O4 Cu1 2.365(3) 2_655 ? O1 C1 1.272(5) . ? O6 C18 1.227(5) . ? O5 C17 1.215(5) . ? N1 C2 1.312(6) . ? N1 C3 1.433(5) . ? N1 H1 0.8800 . ? O3 C1 1.224(5) . ? N2 C17 1.340(5) . ? N2 C16 1.422(5) . ? N2 H2 0.8800 . ? C2 C1 1.539(6) . ? C17 C18 1.549(6) . ? C3 C8 1.386(6) . ? C3 C4 1.402(6) . ? C4 C5 1.386(6) . ? C4 C9 1.519(5) . ? C16 C15 1.388(6) . ? C16 C11 1.398(6) . ? C11 C12 1.397(6) . ? C11 C10 1.511(6) . ? C9 C10 1.531(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C8 C7 1.392(7) . ? C8 H8 0.9500 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C15 C14 1.384(7) . ? C15 H15 0.9500 . ? C5 C6 1.380(6) . ? C5 H5 0.9500 . ? C12 C13 1.398(6) . ? C12 H12 0.9500 . ? C13 C14 1.385(7) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C6 C7 1.379(7) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? O7 C21A 1.434(8) . ? O7 C21B 1.471(18) . ? O7 H7A 0.8000(10) . ? C21A C22A 1.480(17) . ? C21A H21A 0.9900 . ? C21A H21B 0.9900 . ? C22A H22A 0.9800 . ? C22A H22B 0.9800 . ? C22A H22C 0.9800 . ? C21B C22B 1.30(5) . ? C21B H21C 0.9900 . ? C21B H21D 0.9900 . ? C22B H22D 0.9800 . ? C22B H22E 0.9800 . ? C22B H22F 0.9800 . ? O8 C23 1.321(10) . ? O8 H8A 1.017(18) . ? C24 C23 1.552(13) . ? C24 H24A 0.9800 . ? C24 H24C 0.9800 . ? C24 H24B 0.9800 . ? C23 H23B 0.9900 . ? C23 H23A 0.9900 . ? 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 Cu1 O7 91.83(14) . . ? O1 Cu1 O4 174.58(12) . . ? O7 Cu1 O4 93.45(13) . . ? O1 Cu1 O2 84.43(13) . . ? O7 Cu1 O2 174.90(13) . . ? O4 Cu1 O2 90.22(13) . . ? O1 Cu1 O4 103.25(13) . 2_655 ? O7 Cu1 O4 96.82(13) . 2_655 ? O4 Cu1 O4 77.34(13) . 2_655 ? O2 Cu1 O4 87.44(12) . 2_655 ? O1 Cu1 O5 102.05(13) . . ? O7 Cu1 O5 94.70(13) . . ? O4 Cu1 O5 76.30(12) . . ? O2 Cu1 O5 82.72(12) . . ? O4 Cu1 O5 151.76(11) 2_655 . ? C2 O2 Cu1 109.8(3) . . ? C18 O4 Cu1 119.1(3) . . ? C18 O4 Cu1 130.2(3) . 2_655 ? Cu1 O4 Cu1 102.65(13) . 2_655 ? C1 O1 Cu1 113.6(3) . . ? C17 O5 Cu1 101.0(3) . . ? C2 N1 C3 123.8(3) . . ? C2 N1 H1 118.1 . . ? C3 N1 H1 118.1 . . ? C17 N2 C16 125.2(4) . . ? C17 N2 H2 117.4 . . ? C16 N2 H2 117.4 . . ? O2 C2 N1 124.7(4) . . ? O2 C2 C1 118.5(4) . . ? N1 C2 C1 116.7(4) . . ? O5 C17 N2 125.8(4) . . ? O5 C17 C18 122.0(4) . . ? N2 C17 C18 112.2(4) . . ? C8 C3 C4 121.7(4) . . ? C8 C3 N1 117.4(4) . . ? C4 C3 N1 120.8(4) . . ? C5 C4 C3 117.0(4) . . ? C5 C4 C9 123.0(4) . . ? C3 C4 C9 120.0(4) . . ? C15 C16 C11 121.2(4) . . ? C15 C16 N2 119.1(4) . . ? C11 C16 N2 119.7(4) . . ? C12 C11 C16 118.0(4) . . ? C12 C11 C10 120.1(4) . . ? C16 C11 C10 121.8(4) . . ? C4 C9 C10 114.6(3) . . ? C4 C9 H9A 108.6 . . ? C10 C9 H9A 108.6 . . ? C4 C9 H9B 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? O6 C18 O4 127.3(4) . . ? O6 C18 C17 117.8(4) . . ? O4 C18 C17 114.8(4) . . ? C3 C8 C7 119.6(4) . . ? C3 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C11 C10 C9 110.8(3) . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C14 C15 C16 120.1(4) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C6 C5 C4 121.8(4) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? O3 C1 O1 128.4(4) . . ? O3 C1 C2 118.1(4) . . ? O1 C1 C2 113.5(4) . . ? C11 C12 C13 120.8(4) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 120.0(4) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C15 C14 C13 119.9(4) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C7 C6 C5 120.6(4) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 119.2(4) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C21A O7 C21B 36.4(14) . . ? C21A O7 Cu1 122.2(4) . . ? C21B O7 Cu1 131.9(8) . . ? C21A O7 H7A 123(8) . . ? C21B O7 H7A 110(9) . . ? Cu1 O7 H7A 113(8) . . ? O7 C21A C22A 110.6(10) . . ? O7 C21A H21A 109.5 . . ? C22A C21A H21A 109.5 . . ? O7 C21A H21B 109.5 . . ? C22A C21A H21B 109.5 . . ? H21A C21A H21B 108.1 . . ? C22B C21B O7 116(3) . . ? C22B C21B H21C 108.2 . . ? O7 C21B H21C 108.2 . . ? C22B C21B H21D 108.2 . . ? O7 C21B H21D 108.2 . . ? H21C C21B H21D 107.4 . . ? C21B C22B H22D 109.5 . . ? C21B C22B H22E 109.5 . . ? H22D C22B H22E 109.5 . . ? C21B C22B H22F 109.5 . . ? H22D C22B H22F 109.5 . . ? H22E C22B H22F 109.5 . . ? C23 O8 H8A 139(3) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? H24C C24 H24B 109.5 . . ? O8 C23 C24 147.5(13) . . ? O8 C23 H23B 99.9 . . ? C24 C23 H23B 99.9 . . ? O8 C23 H23A 99.9 . . ? C24 C23 H23A 99.9 . . ? H23B C23 H23A 104.2 . . ? _database_code_depnum_ccdc_archive 'CCDC 927505' ####################################################################### # # 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_edpba_f _iucr_refine_instructions_details ; TITL edpba_f in P2(1)/c CELL 0.71073 6.6560 9.1479 16.3406 90.000 93.502 90.000 ZERR 4.00 0.0002 0.0002 0.0004 0.000 0.002 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 44 48 4 12 MERG 2 SHEL 50 0.8 FMAP 2 PLAN 25 ACTA HTAB 2.00000 BOND $H LIST 4 L.S. 20 TEMP -153.00 WGHT 0.047200 0.149700 FVAR 0.15313 O2 4 0.308960 0.098303 0.537130 11.00000 0.04097 0.01693 = 0.05502 0.00274 0.00936 0.00007 O1 4 0.318074 -0.113547 0.607216 11.00000 0.02890 0.01873 = 0.02697 -0.00295 0.00109 -0.00188 N1 3 0.189873 -0.265714 0.482411 11.00000 0.02314 0.01936 = 0.01864 0.00266 0.00021 0.00293 O3 4 0.151459 -0.060987 0.402008 11.00000 0.04005 0.03365 = 0.03853 0.01848 -0.00649 -0.00225 C9 1 0.399276 -0.533177 0.512329 11.00000 0.01843 0.01503 = 0.01726 0.00199 -0.00020 -0.00038 AFIX 23 H9A 2 0.418905 -0.638132 0.525249 11.00000 -1.50000 H9B 2 0.356838 -0.483658 0.562306 11.00000 -1.50000 AFIX 0 C4 1 0.235859 -0.517029 0.444578 11.00000 0.01455 0.02209 = 0.01584 0.00230 0.00316 -0.00270 C8 1 -0.000630 -0.366425 0.362374 11.00000 0.01758 0.03389 = 0.02035 0.00473 0.00162 0.00424 AFIX 43 H8 2 -0.065088 -0.274991 0.352222 11.00000 -1.20000 AFIX 0 C5 1 0.181536 -0.635162 0.394539 11.00000 0.01861 0.02405 = 0.02237 -0.00173 0.00421 -0.00231 AFIX 43 H5 2 0.240587 -0.728109 0.405807 11.00000 -1.20000 AFIX 0 C2 1 0.197911 -0.121432 0.466763 11.00000 0.01612 0.02266 = 0.03123 0.00793 0.00395 0.00316 C3 1 0.140356 -0.382517 0.428036 11.00000 0.01609 0.02360 = 0.01647 0.00185 0.00379 -0.00084 C10 1 0.397909 -0.039469 0.681537 11.00000 0.03541 0.03222 = 0.03230 -0.01514 0.00733 -0.00796 AFIX 23 H10A 2 0.296014 0.028145 0.701840 11.00000 -1.20000 H10B 2 0.519318 0.017658 0.670022 11.00000 -1.20000 AFIX 0 C11 1 0.449800 -0.155317 0.744265 11.00000 0.02765 0.04933 = 0.02430 -0.00949 0.00230 -0.00775 AFIX 133 H11A 2 0.329382 -0.212932 0.753901 11.00000 -1.50000 H11B 2 0.499985 -0.109172 0.795645 11.00000 -1.50000 H11C 2 0.553936 -0.219536 0.724235 11.00000 -1.50000 AFIX 0 C7 1 -0.046291 -0.484831 0.311895 11.00000 0.01620 0.04921 = 0.01880 0.00063 -0.00186 -0.00150 AFIX 43 H7 2 -0.138883 -0.473725 0.265726 11.00000 -1.20000 AFIX 0 C6 1 0.042422 -0.619465 0.328393 11.00000 0.02187 0.03771 = 0.02158 -0.00936 0.00285 -0.00794 AFIX 43 H6 2 0.007983 -0.701052 0.294404 11.00000 -1.20000 AFIX 0 C1 1 0.279745 -0.030854 0.540878 11.00000 0.01867 0.01808 = 0.03731 0.00289 0.00761 0.00365 H1 2 0.228559 -0.286380 0.532954 11.00000 -1.50000 HKLF 4 REM edpba_f in P2(1)/c REM R1 = 0.0325 for 1654 Fo > 4sig(Fo) and 0.0409 for all 2039 data REM 139 parameters refined using 0 restraints END WGHT 0.0471 0.1496 REM Highest difference peak 0.240, deepest hole -0.182, 1-sigma level 0.037 Q1 1 0.3146 -0.5193 0.4768 11.00000 0.05 0.24 Q2 1 0.5000 -0.5000 0.5000 10.50000 0.05 0.23 ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C11 H12 N O3' _chemical_formula_weight 206.22 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.6560(2) _cell_length_b 9.1479(2) _cell_length_c 16.3406(4) _cell_angle_alpha 90 _cell_angle_beta 93.502(2) _cell_angle_gamma 90 _cell_volume 993.10(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6741 _cell_measurement_theta_min 3.2331 _cell_measurement_theta_max 29.4672 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.5761 _exptl_crystal_size_mid 0.175 _exptl_crystal_size_min 0.1204 _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 9 -2 -4 0.2676 0 0 4 0.0676 0 -13 -4 0.0716 0 -3 0 0.0923 0 3 -22 0.0923 0 -3 -1 0.0585 0 13 5 0.0595 -2 0 1 0.2796 1 3 1 0.1325 1 -4 -2 0.0931 -1 -3 -1 0.0914 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_crystal_colour colourless _exptl_crystal_description prismatic _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.99 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4186 _diffrn_orient_matrix_ub_11 -0.0060634 _diffrn_orient_matrix_ub_12 0.0323697 _diffrn_orient_matrix_ub_13 -0.0395423 _diffrn_orient_matrix_ub_21 0.02409 _diffrn_orient_matrix_ub_22 0.0690292 _diffrn_orient_matrix_ub_23 0.0177544 _diffrn_orient_matrix_ub_31 0.1037964 _diffrn_orient_matrix_ub_32 -0.0141319 _diffrn_orient_matrix_ub_33 -0.0036916 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_unetI/netI 0.0198 _diffrn_reflns_number 12200 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 2039 _reflns_number_gt 1654 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.1177P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2039 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.103 _refine_ls_wR_factor_gt 0.0993 _refine_ls_goodness_of_fit_ref 0.94 _refine_ls_restrained_S_all 0.94 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.254 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.038 #----------------------------------------------------------------------------# # 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' 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.30895(15) 0.09833(10) 0.53717(6) 0.0372(3) Uani 1 1 d . . . O1 O 0.31811(13) -0.11352(9) 0.60725(5) 0.0247(2) Uani 1 1 d . . . N1 N 0.18987(14) -0.26575(11) 0.48240(6) 0.0203(2) Uani 1 1 d . . . O3 O 0.15137(14) -0.06099(11) 0.40201(6) 0.0376(3) Uani 1 1 d . . . C9 C 0.39927(15) -0.53319(11) 0.51232(7) 0.0167(3) Uani 1 1 d . . . H9A H 0.4189 -0.6381 0.5252 0.025 Uiso 1 1 calc R . . H9B H 0.3568 -0.4837 0.5623 0.025 Uiso 1 1 calc R . . C4 C 0.23584(16) -0.51705(12) 0.44460(6) 0.0173(3) Uani 1 1 d . . . C8 C -0.00067(18) -0.36643(14) 0.36236(7) 0.0238(3) Uani 1 1 d . . . H8 H -0.0651 -0.275 0.3522 0.029 Uiso 1 1 calc R . . C5 C 0.18154(17) -0.63516(13) 0.39452(7) 0.0214(3) Uani 1 1 d . . . H5 H 0.2407 -0.7281 0.4057 0.026 Uiso 1 1 calc R . . C2 C 0.19792(17) -0.12148(13) 0.46678(8) 0.0230(3) Uani 1 1 d . . . C3 C 0.14039(17) -0.38253(13) 0.42806(7) 0.0184(3) Uani 1 1 d . . . C10 C 0.3979(2) -0.03953(15) 0.68155(8) 0.0329(3) Uani 1 1 d . . . H10A H 0.296 0.0281 0.7019 0.039 Uiso 1 1 calc R . . H10B H 0.5193 0.0176 0.67 0.039 Uiso 1 1 calc R . . C11 C 0.4499(2) -0.15540(16) 0.74427(8) 0.0335(3) Uani 1 1 d . . . H11A H 0.3295 -0.213 0.7539 0.05 Uiso 1 1 calc R . . H11B H 0.5001 -0.1093 0.7956 0.05 Uiso 1 1 calc R . . H11C H 0.554 -0.2196 0.7242 0.05 Uiso 1 1 calc R . . C7 C -0.04633(17) -0.48476(16) 0.31185(7) 0.0280(3) Uani 1 1 d . . . H7 H -0.1388 -0.4736 0.2657 0.034 Uiso 1 1 calc R . . C6 C 0.04236(19) -0.61946(15) 0.32838(7) 0.0267(3) Uani 1 1 d . . . H6 H 0.0078 -0.7011 0.2944 0.032 Uiso 1 1 calc R . . C1 C 0.27975(17) -0.03078(13) 0.54091(8) 0.0243(3) Uani 1 1 d . . . H1 H 0.229(2) -0.2862(17) 0.5333(10) 0.036 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0408(6) 0.0168(5) 0.0548(7) 0.0027(4) 0.0093(5) 0.0001(4) O1 0.0288(5) 0.0185(4) 0.0267(5) -0.0030(3) 0.0010(4) -0.0019(3) N1 0.0229(5) 0.0192(5) 0.0187(5) 0.0027(4) 0.0003(4) 0.0029(4) O3 0.0400(6) 0.0333(6) 0.0385(6) 0.0185(4) -0.0064(4) -0.0022(4) C9 0.0182(6) 0.0149(5) 0.0170(5) 0.0022(4) -0.0004(4) -0.0005(4) C4 0.0144(5) 0.0218(6) 0.0158(5) 0.0024(4) 0.0030(4) -0.0027(4) C8 0.0173(6) 0.0340(7) 0.0200(6) 0.0046(5) 0.0016(5) 0.0042(5) C5 0.0185(6) 0.0240(6) 0.0220(6) -0.0017(5) 0.0041(5) -0.0023(4) C2 0.0163(6) 0.0221(6) 0.0309(7) 0.0076(5) 0.0037(5) 0.0029(4) C3 0.0158(5) 0.0234(6) 0.0162(5) 0.0017(4) 0.0037(4) -0.0009(4) C10 0.0351(7) 0.0318(7) 0.0324(7) -0.0149(6) 0.0074(6) -0.0077(6) C11 0.0275(7) 0.0491(9) 0.0240(6) -0.0093(6) 0.0025(5) -0.0076(6) C7 0.0160(6) 0.0490(8) 0.0186(6) 0.0006(6) -0.0020(4) -0.0017(5) C6 0.0215(6) 0.0376(7) 0.0212(6) -0.0090(5) 0.0028(5) -0.0077(5) C1 0.0186(6) 0.0177(6) 0.0373(7) 0.0030(5) 0.0074(5) 0.0036(4) #----------------------------------------------------------------------------# # 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 O2 C1 1.1991(15) . ? O1 C1 1.3340(15) . ? O1 C10 1.4614(15) . ? N1 C2 1.3458(15) . ? N1 C3 1.4151(15) . ? N1 H1 0.876(15) . ? O3 C2 1.2174(15) . ? C9 C4 1.5109(15) . ? C9 C9 1.548(2) 3_646 ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C4 C5 1.3898(16) . ? C4 C3 1.4035(16) . ? C8 C7 1.3838(18) . ? C8 C3 1.3901(16) . ? C8 H8 0.95 . ? C5 C6 1.3872(17) . ? C5 H5 0.95 . ? C2 C1 1.5401(18) . ? C10 C11 1.500(2) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C7 C6 1.3858(19) . ? C7 H7 0.95 . ? C6 H6 0.95 . ? 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 C1 O1 C10 117.01(10) . . ? C2 N1 C3 129.18(10) . . ? C2 N1 H1 112.2(10) . . ? C3 N1 H1 118.5(10) . . ? C4 C9 C9 111.57(11) . 3_646 ? C4 C9 H9A 109.3 . . ? C9 C9 H9A 109.3 3_646 . ? C4 C9 H9B 109.3 . . ? C9 C9 H9B 109.3 3_646 . ? H9A C9 H9B 108 . . ? C5 C4 C3 118.03(10) . . ? C5 C4 C9 120.33(10) . . ? C3 C4 C9 121.59(10) . . ? C7 C8 C3 119.42(11) . . ? C7 C8 H8 120.3 . . ? C3 C8 H8 120.3 . . ? C6 C5 C4 121.03(11) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? O3 C2 N1 126.84(12) . . ? O3 C2 C1 119.85(11) . . ? N1 C2 C1 113.29(10) . . ? C8 C3 C4 121.20(11) . . ? C8 C3 N1 121.66(11) . . ? C4 C3 N1 117.12(10) . . ? O1 C10 C11 107.29(10) . . ? O1 C10 H10A 110.3 . . ? C11 C10 H10A 110.3 . . ? O1 C10 H10B 110.3 . . ? C11 C10 H10B 110.3 . . ? H10A C10 H10B 108.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C7 C6 120.25(11) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C6 C5 120.01(11) . . ? C7 C6 H6 120 . . ? C5 C6 H6 120 . . ? O2 C1 O1 125.22(12) . . ? O2 C1 C2 122.77(12) . . ? O1 C1 C2 111.99(10) . . ? _database_code_depnum_ccdc_archive 'CCDC 927506' ####################################################################### # # 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_Cued_Bu4N _iucr_refine_instructions_details ; TITL Cued_Bu4N CELL 0.71073 14.2234 17.5944 21.3698 90.000 90.000 90.000 ZERR 2.00 0.0002 0.0004 0.0004 0.000 0.000 0.000 LATT -2 SYMM - X, - Y, Z SYMM - X, Y, - Z SYMM X, - Y, - Z SFAC C H N O CU UNIT 200 328 16 32 4 MERG 2 SHEL 50 0.8 FMAP 2 PLAN 20 ACTA BOND $H HTAB LIST 3 L.S. 50 TEMP 20 WGHT 0.099400 3.141100 FVAR 1.82404 0.50000 CU1 5 1.000000 0.812722 1.000000 10.50000 0.01342 0.03835 = 0.02384 0.00000 -0.00065 0.00000 O1 4 1.054176 0.795659 0.917451 11.00000 0.01885 0.05343 = 0.02744 -0.00466 0.00096 0.00832 N1 3 0.885729 0.833482 0.953561 11.00000 0.01536 0.02954 = 0.02693 -0.00615 -0.00269 0.00206 O2 4 1.017131 0.806772 0.816709 11.00000 0.03088 0.06115 = 0.02782 -0.00993 0.00322 0.00688 O3 4 0.839263 0.854392 0.852426 11.00000 0.03172 0.08445 = 0.02766 -0.00995 -0.00563 0.02032 N2 3 0.285755 0.695533 0.820251 11.00000 0.02259 0.04196 = 0.03336 -0.01209 0.00405 0.00231 C2 1 0.896880 0.835154 0.892536 11.00000 0.02099 0.03933 = 0.02749 -0.00926 -0.00413 0.00694 C3 1 0.796381 0.851956 0.979635 11.00000 0.01547 0.04408 = 0.02232 -0.00449 -0.00238 0.00414 C4 1 0.718864 0.806362 0.966218 11.00000 0.02132 0.03675 = 0.03016 -0.00045 -0.00079 0.00110 AFIX 43 H4A 2 0.725305 0.765698 0.938746 11.00000 -1.20000 AFIX 0 C22 1 0.388868 0.672312 0.815340 11.00000 0.02040 0.04760 = 0.03339 -0.00662 0.00431 0.00419 AFIX 23 H22A 2 0.395577 0.621157 0.831667 11.00000 -1.20000 H22B 2 0.406301 0.671057 0.771469 11.00000 -1.20000 AFIX 0 C1 1 0.997952 0.810560 0.872597 11.00000 0.02222 0.03831 = 0.02450 -0.00847 0.00091 0.00289 C8 1 0.785775 0.914301 1.019726 11.00000 0.02115 0.04994 = 0.03088 -0.01479 -0.00277 0.00464 C6 1 0.622064 0.880413 1.035218 11.00000 0.02110 0.06788 = 0.03703 0.00104 0.00587 0.00689 AFIX 43 H6A 2 0.564671 0.889300 1.054743 11.00000 -1.20000 AFIX 0 C7 1 0.699080 0.926703 1.047627 11.00000 0.02657 0.06222 = 0.03885 -0.01846 0.00202 0.01009 AFIX 43 H7A 2 0.692276 0.967051 1.075373 11.00000 -1.20000 AFIX 0 C13 1 0.271003 0.776564 0.799608 11.00000 0.02815 0.03904 = 0.05527 -0.01692 -0.00455 0.00108 AFIX 23 H13A 2 0.204414 0.788096 0.802033 11.00000 -1.20000 H13B 2 0.303271 0.809881 0.828706 11.00000 -1.20000 AFIX 0 C5 1 0.632075 0.821018 0.993448 11.00000 0.01568 0.05531 = 0.03873 0.00152 0.00039 -0.00221 AFIX 43 H5A 2 0.580560 0.790772 0.983541 11.00000 -1.20000 AFIX 0 C18 1 0.251069 0.691067 0.887284 11.00000 0.02845 0.07187 = 0.03509 -0.02037 0.00711 -0.00343 AFIX 23 H18A 2 0.184216 0.701946 0.887720 11.00000 -1.20000 H18B 2 0.282159 0.730385 0.911455 11.00000 -1.20000 AFIX 0 C16 1 0.080114 0.586873 0.738898 11.00000 0.02432 0.04487 = 0.05338 -0.00564 0.00185 -0.00394 AFIX 23 H16A 2 0.093547 0.539884 0.760890 11.00000 -1.20000 H16B 2 0.012609 0.594571 0.740104 11.00000 -1.20000 AFIX 0 C14 1 0.232269 0.640562 0.777784 11.00000 0.02722 0.03504 = 0.03360 -0.01521 0.00414 -0.00203 AFIX 43 H14A 2 0.262562 0.602190 0.755664 11.00000 -1.20000 AFIX 0 C9 1 0.863935 0.971398 1.027749 11.00000 0.02174 0.05677 = 0.04852 -0.03019 -0.00421 0.00570 AFIX 23 H9A 2 0.923894 0.945211 1.029453 11.00000 -1.20000 H9B 2 0.855491 0.998663 1.066798 11.00000 -1.20000 AFIX 0 C15 1 0.127479 0.652339 0.773950 11.00000 0.02743 0.05815 = 0.05078 -0.02083 -0.00171 0.00571 AFIX 23 H15A 2 0.114464 0.699789 0.752524 11.00000 -1.20000 H15B 2 0.101668 0.655805 0.815868 11.00000 -1.20000 AFIX 0 C17 1 0.109645 0.577950 0.672043 11.00000 0.03859 0.09082 = 0.05803 -0.03341 0.00593 -0.02539 AFIX 33 H17A 2 0.077038 0.535629 0.653796 11.00000 -1.50000 H17B 2 0.176184 0.569086 0.670171 11.00000 -1.50000 H17C 2 0.094647 0.623415 0.649300 11.00000 -1.50000 AFIX 0 C24 1 0.554651 0.685954 0.853235 11.00000 0.02757 0.07272 = 0.05253 -0.00378 -0.00121 0.00098 AFIX 23 H24A 2 0.569811 0.664776 0.812560 11.00000 -1.20000 H24B 2 0.601361 0.724410 0.862791 11.00000 -1.20000 AFIX 0 C23 1 0.457098 0.723994 0.849766 11.00000 0.02406 0.06371 = 0.04343 -0.01409 0.00381 0.00145 AFIX 23 H23A 2 0.434005 0.733791 0.891707 11.00000 -1.20000 H23B 2 0.462041 0.772206 0.827996 11.00000 -1.20000 AFIX 0 C12 1 0.304717 0.794074 0.734560 11.00000 0.04363 0.03664 = 0.05623 -0.00318 -0.01244 -0.00484 AFIX 23 H12A 2 0.267942 0.765464 0.704453 11.00000 -1.20000 H12B 2 0.369963 0.778880 0.730325 11.00000 -1.20000 AFIX 0 C10 1 0.337150 0.897503 0.657493 11.00000 0.12314 0.06942 = 0.08674 0.02750 -0.05245 -0.02914 AFIX 33 H10A 2 0.330961 0.951034 0.649833 11.00000 -1.50000 H10B 2 0.304345 0.869747 0.625570 11.00000 -1.50000 H10C 2 0.402469 0.883779 0.656919 11.00000 -1.50000 AFIX 0 C11 1 0.295434 0.878408 0.721131 11.00000 0.05730 0.04048 = 0.09336 0.00348 -0.03100 -0.00781 AFIX 23 H11A 2 0.327755 0.907149 0.753343 11.00000 -1.20000 H11B 2 0.229578 0.892700 0.721895 11.00000 -1.20000 AFIX 0 C20 1 0.216647 0.610045 0.981495 11.00000 0.08122 0.08350 = 0.06189 -0.01548 0.02803 -0.03052 AFIX 23 H20A 2 0.239924 0.566306 1.004376 11.00000 -1.20000 H20B 2 0.232482 0.654974 1.005597 11.00000 -1.20000 AFIX 0 C19 1 0.267469 0.614085 0.919829 11.00000 0.05802 0.10023 = 0.04398 0.00984 0.01244 0.01486 AFIX 23 H19A 2 0.245578 0.573432 0.892852 11.00000 -1.20000 H19B 2 0.334288 0.606908 0.926726 11.00000 -1.20000 AFIX 0 C25 1 0.560529 0.623940 0.901507 11.00000 0.04469 0.10617 = 0.08429 0.01722 -0.01352 0.01134 AFIX 33 H25A 2 0.622251 0.601879 0.900796 11.00000 -1.50000 H25B 2 0.514662 0.585495 0.892331 11.00000 -1.50000 H25C 2 0.548426 0.644859 0.942208 11.00000 -1.50000 AFIX 0 C21 1 0.114973 0.604545 0.977744 11.00000 0.07023 0.10430 = 0.15581 0.04209 0.04195 -0.00053 AFIX 137 H21A 2 0.089002 0.653873 0.969388 11.00000 -1.50000 H21B 2 0.090694 0.585814 1.016721 11.00000 -1.50000 H21C 2 0.097980 0.570309 0.944643 11.00000 -1.50000 PART 1 OW1 4 0.444459 0.491304 0.738987 10.50000 0.18889 0.02157 = 0.04510 0.00270 0.01954 0.01289 PART 2 OW2 4 0.421728 0.486315 0.793564 10.50000 0.14711 0.06145 = 0.06151 0.00419 0.01616 -0.00020 PART 0 REM do_zero REM R1 = 0.0538 for 5208 Fo > 4sig(Fo) and 0.0578 for all 5497 data REM 291 parameters refined using 0 restraints HKLF 4 REM Cued_Bu4N REM R1 = 0.0490 for 5208 Fo > 4sig(Fo) and 0.0528 for all 5497 data REM 290 parameters refined using 0 restraints END WGHT 0.0994 3.1497 REM Highest difference peak 1.295, deepest hole -0.388, 1-sigma level 0.101 Q1 1 0.3975 0.4915 0.6907 11.00000 0.05 1.30 Q2 1 0.9992 0.8072 1.0426 11.00000 0.05 0.87 Q3 1 0.2619 0.6488 0.7357 11.00000 0.05 0.51 ; _audit_creation_date 2012-07-11T21:57:35-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_formula_sum 'C100 H164 Cu2 N8 O16' _chemical_formula_weight 1861.47 _chemical_formula_moiety 'C36 H24 Cu2 N4 O12, 4(C16 H35 N), 4(O)' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'I 2 2 2' _symmetry_space_group_name_hall 'I 2 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x, y, -z' 'x, -y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' _cell_length_a 14.2234(2) _cell_length_b 17.5944(4) _cell_length_c 21.3698(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5347.84(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22533 _cell_measurement_theta_min 1.8374 _cell_measurement_theta_max 29.5331 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.4166 _exptl_crystal_size_mid 0.3933 _exptl_crystal_size_min 0.3814 _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2076 _exptl_crystal_description Prismatic _exptl_crystal_colour 'light blue' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 1 0.1397 -1 1 0 0.2189 1 0 -1 0.1815 -1 2 -2 0.2089 1 -2 -2 0.1941 0 0 -1 0.1854 -1 -1 -1 0.1683 -1 -4 -2 0.1578 -2 1 -1 0.2124 0 2 1 0.1988 2 -1 1 0.1788 -1 1 1 0.1996 0 2 -1 0.219 2 -1 -2 0.1841 3 2 3 0.1985 0 0 1 0.2037 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.46 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.929 _exptl_absorpt_correction_T_max 0.937 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4186 _diffrn_orient_matrix_ub_11 0.0359037 _diffrn_orient_matrix_ub_12 0.0134459 _diffrn_orient_matrix_ub_13 0.0202 _diffrn_orient_matrix_ub_21 -0.0248184 _diffrn_orient_matrix_ub_22 -0.0146427 _diffrn_orient_matrix_ub_23 0.0261547 _diffrn_orient_matrix_ub_31 0.0241179 _diffrn_orient_matrix_ub_32 -0.0350636 _diffrn_orient_matrix_ub_33 -0.0031669 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_unetI/netI 0.0195 _diffrn_reflns_number 55826 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 5497 _reflns_number_gt 5208 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SUPERFLIP (Palatinus, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'publcif (Westrip, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1781P)^2^+5.8980P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5497 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1500 _refine_ls_wR_factor_gt 0.1443 _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_restrained_S_all 1.167 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.012(15) _refine_diff_density_max 1.295 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.101 #----------------------------------------------------------------------------# # 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' Cu Cu 0.3201 1.2651 '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 1.0000 0.81272(2) 1.0000 0.02521(14) Uani 1 2 d S . . O1 O 1.05418(15) 0.79566(13) 0.91745(10) 0.0332(5) Uani 1 1 d . . . N1 N 0.88573(16) 0.83348(13) 0.95356(11) 0.0239(5) Uani 1 1 d . . . O2 O 1.01713(15) 0.80677(15) 0.81671(10) 0.0400(5) Uani 1 1 d . . . O3 O 0.83926(18) 0.85439(18) 0.85243(11) 0.0479(7) Uani 1 1 d . . . N2 N 0.28575(18) 0.69553(16) 0.82025(12) 0.0326(6) Uani 1 1 d . . . C2 C 0.8969(2) 0.83515(17) 0.89254(14) 0.0293(6) Uani 1 1 d . . . C3 C 0.79638(19) 0.85196(18) 0.97964(13) 0.0273(6) Uani 1 1 d . . . C4 C 0.7189(2) 0.80636(18) 0.96622(13) 0.0294(6) Uani 1 1 d . . . H4A H 0.7253 0.7657 0.9387 0.035 Uiso 1 1 calc R . . C22 C 0.3889(2) 0.67231(19) 0.81534(15) 0.0338(7) Uani 1 1 d . . . H22A H 0.3956 0.6212 0.8317 0.041 Uiso 1 1 calc R . . H22B H 0.4063 0.6711 0.7715 0.041 Uiso 1 1 calc R . . C1 C 0.9980(2) 0.81056(15) 0.87260(12) 0.0283(5) Uani 1 1 d . . . C8 C 0.7858(2) 0.9143(2) 1.01973(14) 0.0340(7) Uani 1 1 d . . . C6 C 0.6221(2) 0.8804(2) 1.03522(16) 0.0420(8) Uani 1 1 d . . . H6A H 0.5647 0.8893 1.0547 0.050 Uiso 1 1 calc R . . C7 C 0.6991(2) 0.9267(2) 1.04763(17) 0.0425(8) Uani 1 1 d . . . H7A H 0.6923 0.9671 1.0754 0.051 Uiso 1 1 calc R . . C13 C 0.2710(2) 0.77656(19) 0.79961(18) 0.0408(8) Uani 1 1 d . . . H13A H 0.2044 0.7881 0.8020 0.049 Uiso 1 1 calc R . . H13B H 0.3033 0.8099 0.8287 0.049 Uiso 1 1 calc R . . C5 C 0.63208(19) 0.82102(19) 0.99345(17) 0.0366(7) Uani 1 1 d . . . H5A H 0.5806 0.7908 0.9835 0.044 Uiso 1 1 calc R . . C18 C 0.2511(2) 0.6911(2) 0.88728(16) 0.0451(8) Uani 1 1 d . . . H18A H 0.1842 0.7019 0.8877 0.054 Uiso 1 1 calc R . . H18B H 0.2822 0.7304 0.9115 0.054 Uiso 1 1 calc R . . C16 C 0.0801(2) 0.5869(2) 0.73890(18) 0.0409(7) Uani 1 1 d . . . H16A H 0.0935 0.5399 0.7609 0.049 Uiso 1 1 calc R . . H16B H 0.0126 0.5946 0.7401 0.049 Uiso 1 1 calc R . . C14 C 0.2323(2) 0.64056(19) 0.77778(15) 0.0320(7) Uani 1 1 d . . . H14A H 0.2626 0.6022 0.7557 0.038 Uiso 1 1 calc R . . C9 C 0.8639(2) 0.9714(2) 1.02775(17) 0.0423(8) Uani 1 1 d . . . H9A H 0.9239 0.9452 1.0295 0.051 Uiso 1 1 calc R . . H9B H 0.8555 0.9987 1.0668 0.051 Uiso 1 1 calc R . . C15 C 0.1275(2) 0.6523(2) 0.77395(19) 0.0455(9) Uani 1 1 d . . . H15A H 0.1145 0.6998 0.7525 0.055 Uiso 1 1 calc R . . H15B H 0.1017 0.6558 0.8159 0.055 Uiso 1 1 calc R . . C17 C 0.1096(3) 0.5780(3) 0.6720(2) 0.0625(13) Uani 1 1 d . . . H17A H 0.0770 0.5356 0.6538 0.094 Uiso 1 1 calc R . . H17B H 0.1762 0.5691 0.6702 0.094 Uiso 1 1 calc R . . H17C H 0.0946 0.6234 0.6493 0.094 Uiso 1 1 calc R . . C24 C 0.5547(3) 0.6860(3) 0.8532(2) 0.0509(9) Uani 1 1 d . . . H24A H 0.5698 0.6648 0.8126 0.061 Uiso 1 1 calc R . . H24B H 0.6014 0.7244 0.8628 0.061 Uiso 1 1 calc R . . C23 C 0.4571(2) 0.7240(3) 0.84977(18) 0.0437(8) Uani 1 1 d . . . H23A H 0.4340 0.7338 0.8917 0.052 Uiso 1 1 calc R . . H23B H 0.4620 0.7722 0.8280 0.052 Uiso 1 1 calc R . . C12 C 0.3047(3) 0.7941(2) 0.73456(19) 0.0455(8) Uani 1 1 d . . . H12A H 0.2679 0.7655 0.7045 0.055 Uiso 1 1 calc R . . H12B H 0.3700 0.7789 0.7303 0.055 Uiso 1 1 calc R . . C10 C 0.3371(5) 0.8975(3) 0.6575(3) 0.093(2) Uani 1 1 d . . . H10A H 0.3310 0.9510 0.6498 0.140 Uiso 1 1 calc R . . H10B H 0.3043 0.8697 0.6256 0.140 Uiso 1 1 calc R . . H10C H 0.4025 0.8838 0.6569 0.140 Uiso 1 1 calc R . . C11 C 0.2954(4) 0.8784(2) 0.7211(3) 0.0637(14) Uani 1 1 d . . . H11A H 0.3278 0.9071 0.7533 0.076 Uiso 1 1 calc R . . H11B H 0.2296 0.8927 0.7219 0.076 Uiso 1 1 calc R . . C20 C 0.2166(4) 0.6100(3) 0.9815(2) 0.0755(16) Uani 1 1 d . . . H20A H 0.2399 0.5663 1.0044 0.091 Uiso 1 1 calc R . . H20B H 0.2325 0.6550 1.0056 0.091 Uiso 1 1 calc R . . C19 C 0.2675(4) 0.6141(3) 0.9198(2) 0.0674(13) Uani 1 1 d . . . H19A H 0.2456 0.5734 0.8929 0.081 Uiso 1 1 calc R . . H19B H 0.3343 0.6069 0.9267 0.081 Uiso 1 1 calc R . . C25 C 0.5605(4) 0.6239(4) 0.9015(3) 0.0784(15) Uani 1 1 d . . . H25A H 0.6223 0.6019 0.9008 0.118 Uiso 1 1 calc R . . H25B H 0.5147 0.5855 0.8923 0.118 Uiso 1 1 calc R . . H25C H 0.5484 0.6449 0.9422 0.118 Uiso 1 1 calc R . . C21 C 0.1150(3) 0.6045(4) 0.9777(2) 0.110(3) Uani 1 1 d . . . H21A H 0.0890 0.6539 0.9694 0.165 Uiso 1 1 calc R . . H21B H 0.0907 0.5858 1.0167 0.165 Uiso 1 1 calc R . . H21C H 0.0980 0.5703 0.9446 0.165 Uiso 1 1 calc R . . OW1 O 0.4445(3) 0.4913(2) 0.73899(19) 0.085(3) Uani 0.50 1 d PR . 1 OW2 O 0.4217(3) 0.4863(2) 0.7936(2) 0.090(3) Uani 0.50 1 d PR A 2 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 0.0134(2) 0.0383(2) 0.0238(2) 0.000 -0.00065(19) 0.000 O1 0.0189(10) 0.0534(13) 0.0274(10) -0.0047(9) 0.0010(8) 0.0083(9) N1 0.0154(10) 0.0295(11) 0.0269(11) -0.0062(9) -0.0027(9) 0.0021(8) O2 0.0309(13) 0.0611(14) 0.0278(10) -0.0099(10) 0.0032(8) 0.0069(11) O3 0.0317(13) 0.0844(19) 0.0277(11) -0.0100(12) -0.0056(10) 0.0203(13) N2 0.0226(12) 0.0420(14) 0.0334(13) -0.0121(11) 0.0041(10) 0.0023(11) C2 0.0210(14) 0.0393(15) 0.0275(14) -0.0093(11) -0.0041(11) 0.0069(11) C3 0.0155(12) 0.0441(16) 0.0223(12) -0.0045(11) -0.0024(9) 0.0041(11) C4 0.0213(13) 0.0367(15) 0.0302(14) -0.0005(12) -0.0008(11) 0.0011(12) C22 0.0204(14) 0.0476(18) 0.0334(15) -0.0066(13) 0.0043(11) 0.0042(12) C1 0.0222(12) 0.0383(13) 0.0245(11) -0.0085(10) 0.0009(12) 0.0029(19) C8 0.0212(13) 0.0499(18) 0.0309(14) -0.0148(12) -0.0028(11) 0.0046(13) C6 0.0211(15) 0.068(2) 0.0370(18) 0.0010(15) 0.0059(13) 0.0069(14) C7 0.0266(16) 0.062(2) 0.0389(17) -0.0185(16) 0.0020(13) 0.0101(15) C13 0.0282(16) 0.0390(17) 0.055(2) -0.0169(15) -0.0046(14) 0.0011(13) C5 0.0157(11) 0.0553(17) 0.0387(16) 0.0015(17) 0.0004(12) -0.0022(11) C18 0.0284(16) 0.072(2) 0.0351(16) -0.0204(17) 0.0071(13) -0.0034(17) C16 0.0243(15) 0.0449(18) 0.053(2) -0.0056(16) 0.0018(14) -0.0039(13) C14 0.0272(16) 0.0350(15) 0.0336(15) -0.0152(13) 0.0041(12) -0.0020(13) C9 0.0217(14) 0.0568(19) 0.0485(18) -0.0302(15) -0.0042(13) 0.0057(13) C15 0.0274(17) 0.058(2) 0.051(2) -0.0208(17) -0.0017(14) 0.0057(15) C17 0.039(2) 0.091(3) 0.058(2) -0.033(2) 0.0059(18) -0.025(2) C24 0.0276(17) 0.073(3) 0.053(2) -0.004(2) -0.0012(15) 0.0010(19) C23 0.0241(16) 0.064(2) 0.0434(19) -0.0141(17) 0.0038(14) 0.0014(16) C12 0.044(2) 0.0366(17) 0.056(2) -0.0032(15) -0.0124(16) -0.0048(14) C10 0.123(6) 0.069(3) 0.087(4) 0.028(3) -0.052(4) -0.029(3) C11 0.057(3) 0.040(2) 0.093(4) 0.003(2) -0.031(3) -0.0078(18) C20 0.081(4) 0.083(3) 0.062(3) -0.015(2) 0.028(2) -0.031(3) C19 0.058(3) 0.100(4) 0.044(2) 0.010(2) 0.012(2) 0.015(3) C25 0.045(3) 0.106(4) 0.084(4) 0.017(3) -0.014(2) 0.011(2) C21 0.070(4) 0.104(5) 0.156(8) 0.042(5) 0.042(4) -0.001(4) OW1 0.189(8) 0.022(3) 0.045(3) 0.003(2) 0.020(4) 0.013(4) OW2 0.147(8) 0.061(5) 0.062(4) 0.004(3) 0.016(5) 0.000(4) #----------------------------------------------------------------------------# # 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 N1 1.939(2) . ? Cu1 N1 1.939(2) 3_757 ? Cu1 O1 1.948(2) . ? Cu1 O1 1.948(2) 3_757 ? O1 C1 1.276(4) . ? N1 C2 1.314(4) . ? N1 C3 1.425(4) . ? O2 C1 1.227(3) . ? O3 C2 1.233(4) . ? N2 C13 1.507(5) . ? N2 C18 1.517(4) . ? N2 C22 1.526(4) . ? N2 C14 1.529(4) . ? C2 C1 1.561(4) . ? C3 C4 1.393(4) . ? C3 C8 1.400(4) . ? C4 C5 1.389(4) . ? C4 H4A 0.9300 . ? C22 C23 1.520(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C8 C7 1.387(5) . ? C8 C9 1.508(5) . ? C6 C5 1.382(5) . ? C6 C7 1.391(5) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C13 C12 1.502(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C5 H5A 0.9300 . ? C18 C19 1.540(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C16 C17 1.497(6) . ? C16 C15 1.530(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C14 C15 1.507(5) . ? C14 H14A 0.9300 . ? C9 C9 1.555(9) 4_577 ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C24 C25 1.504(8) . ? C24 C23 1.542(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C12 C11 1.517(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C10 C11 1.521(9) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C20 C21 1.452(7) . ? C20 C19 1.505(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? OW1 OW1 1.609(9) 2_665 ? 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 N1 Cu1 N1 158.29(14) . 3_757 ? N1 Cu1 O1 84.10(9) . . ? N1 Cu1 O1 99.26(9) 3_757 . ? N1 Cu1 O1 99.26(9) . 3_757 ? N1 Cu1 O1 84.09(9) 3_757 3_757 ? O1 Cu1 O1 162.27(14) . 3_757 ? C1 O1 Cu1 113.63(18) . . ? C2 N1 C3 119.4(2) . . ? C2 N1 Cu1 114.27(19) . . ? C3 N1 Cu1 126.18(18) . . ? C13 N2 C18 106.3(3) . . ? C13 N2 C22 111.5(3) . . ? C18 N2 C22 111.3(3) . . ? C13 N2 C14 110.8(3) . . ? C18 N2 C14 111.5(2) . . ? C22 N2 C14 105.5(2) . . ? O3 C2 N1 128.0(3) . . ? O3 C2 C1 119.9(3) . . ? N1 C2 C1 112.1(2) . . ? C4 C3 C8 119.5(3) . . ? C4 C3 N1 119.6(3) . . ? C8 C3 N1 120.9(3) . . ? C5 C4 C3 120.7(3) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C23 C22 N2 114.8(3) . . ? C23 C22 H22A 108.6 . . ? N2 C22 H22A 108.6 . . ? C23 C22 H22B 108.6 . . ? N2 C22 H22B 108.6 . . ? H22A C22 H22B 107.5 . . ? O2 C1 O1 125.5(3) . . ? O2 C1 C2 119.1(3) . . ? O1 C1 C2 115.4(2) . . ? C7 C8 C3 118.8(3) . . ? C7 C8 C9 120.1(3) . . ? C3 C8 C9 120.8(3) . . ? C5 C6 C7 119.0(3) . . ? C5 C6 H6A 120.5 . . ? C7 C6 H6A 120.5 . . ? C8 C7 C6 121.8(3) . . ? C8 C7 H7A 119.1 . . ? C6 C7 H7A 119.1 . . ? C12 C13 N2 114.9(3) . . ? C12 C13 H13A 108.6 . . ? N2 C13 H13A 108.6 . . ? C12 C13 H13B 108.6 . . ? N2 C13 H13B 108.6 . . ? H13A C13 H13B 107.5 . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? N2 C18 C19 115.0(3) . . ? N2 C18 H18A 108.5 . . ? C19 C18 H18A 108.5 . . ? N2 C18 H18B 108.5 . . ? C19 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C17 C16 C15 115.0(3) . . ? C17 C16 H16A 108.5 . . ? C15 C16 H16A 108.5 . . ? C17 C16 H16B 108.5 . . ? C15 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C15 C14 N2 115.9(3) . . ? C15 C14 H14A 122.0 . . ? N2 C14 H14A 122.0 . . ? C8 C9 C9 110.1(3) . 4_577 ? C8 C9 H9A 109.6 . . ? C9 C9 H9A 109.6 4_577 . ? C8 C9 H9B 109.6 . . ? C9 C9 H9B 109.6 4_577 . ? H9A C9 H9B 108.1 . . ? C14 C15 C16 111.0(3) . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C25 C24 C23 113.4(4) . . ? C25 C24 H24A 108.9 . . ? C23 C24 H24A 108.9 . . ? C25 C24 H24B 108.9 . . ? C23 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? C22 C23 C24 109.8(3) . . ? C22 C23 H23A 109.7 . . ? C24 C23 H23A 109.7 . . ? C22 C23 H23B 109.7 . . ? C24 C23 H23B 109.7 . . ? H23A C23 H23B 108.2 . . ? C13 C12 C11 110.4(4) . . ? C13 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? C13 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C10 110.6(5) . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C21 C20 C19 115.7(5) . . ? C21 C20 H20A 108.4 . . ? C19 C20 H20A 108.4 . . ? C21 C20 H20B 108.4 . . ? C19 C20 H20B 108.4 . . ? H20A C20 H20B 107.4 . . ? C20 C19 C18 111.4(4) . . ? C20 C19 H19A 109.4 . . ? C18 C19 H19A 109.4 . . ? C20 C19 H19B 109.4 . . ? C18 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 927507'