# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Matti Haukka' _publ_contact_author_email matti.haukka@uef.fi _publ_author_name M.Haukka data_1 _database_code_depnum_ccdc_archive 'CCDC 871999' #TrackingRef 'Laurila.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 Cl2 N4 O4 Rh2' _chemical_formula_sum 'C14 H14 Cl2 N4 O4 Rh2' _chemical_formula_weight 579.01 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _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 6.6041(11) _cell_length_b 19.562(4) _cell_length_c 14.734(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.627(7) _cell_angle_gamma 90.00 _cell_volume 1902.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9426 _cell_measurement_theta_min 3.26 _cell_measurement_theta_max 36.58 _exptl_crystal_description block _exptl_crystal_colour 'green with metallic shine' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.021 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 2.042 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5100 _exptl_absorpt_correction_T_max 0.7829 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _publ_section_exptl_refinement ; The hydrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C---H = 0.95-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 1.44 \%A from atom H15 and the deepest hole is located 0.65 \%A from atom Rh1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'curved graphite crystal' _diffrn_measurement_device_type 'Bruker KAPPA APEX II DUO CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_reflns_number 33543 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 36.60 _reflns_number_total 9267 _reflns_number_gt 7922 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2g (Brandenburg, 2011)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0058P)^2^+2.4855P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9267 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0224 _refine_ls_wR_factor_ref 0.0477 _refine_ls_wR_factor_gt 0.0437 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 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 Rh1 Rh 0.601925(15) 0.588335(5) 0.728001(7) 0.01226(2) Uani 1 1 d . . . Rh2 Rh 0.120930(15) 0.595126(5) 0.721079(7) 0.01221(2) Uani 1 1 d . . . Cl1 Cl 0.60591(6) 0.469100(18) 0.76230(3) 0.02058(6) Uani 1 1 d . . . Cl2 Cl 0.09477(6) 0.651513(19) 0.57882(2) 0.02006(6) Uani 1 1 d . . . O1 O 0.60997(18) 0.73405(6) 0.66983(8) 0.0221(2) Uani 1 1 d . . . O2 O 0.64365(19) 0.55069(7) 0.53242(8) 0.0249(2) Uani 1 1 d . . . O3 O 0.13369(18) 0.51561(6) 0.89313(8) 0.0224(2) Uani 1 1 d . . . O4 O 0.0539(2) 0.46227(7) 0.62260(9) 0.0288(3) Uani 1 1 d . . . N1 N 0.56258(17) 0.60945(6) 0.86650(8) 0.01293(18) Uani 1 1 d . . . N2 N 0.42295(17) 0.64437(6) 0.99254(8) 0.01361(18) Uani 1 1 d . . . N3 N 0.17750(16) 0.69061(6) 0.78402(8) 0.01316(18) Uani 1 1 d . . . N4 N 0.32793(17) 0.77343(6) 0.86407(8) 0.01428(19) Uani 1 1 d . . . C1 C 0.6066(2) 0.67926(8) 0.69435(10) 0.0164(2) Uani 1 1 d . . . C2 C 0.6288(2) 0.56530(8) 0.60656(10) 0.0170(2) Uani 1 1 d . . . C3 C 0.1300(2) 0.54698(7) 0.82909(10) 0.0166(2) Uani 1 1 d . . . C4 C 0.0792(2) 0.51241(8) 0.66035(11) 0.0185(2) Uani 1 1 d . . . C10 C 0.6379(2) 0.57060(7) 0.93822(9) 0.0149(2) Uani 1 1 d . . . H10 H 0.7343 0.5348 0.9337 0.018 Uiso 1 1 calc R . . C11 C 0.5523(2) 0.59173(7) 1.01617(9) 0.0155(2) Uani 1 1 d . . . H11 H 0.5769 0.5737 1.0753 0.019 Uiso 1 1 calc R . . C12 C 0.43304(19) 0.65394(7) 0.90179(9) 0.0123(2) Uani 1 1 d . . . C13 C 0.31455(19) 0.70481(7) 0.85072(9) 0.01222(19) Uani 1 1 d . . . C14 C 0.1929(2) 0.80426(7) 0.80368(10) 0.0169(2) Uani 1 1 d . . . H14 H 0.1686 0.8519 0.7973 0.020 Uiso 1 1 calc R . . C15 C 0.1010(2) 0.75293(7) 0.75496(10) 0.0158(2) Uani 1 1 d . . . H15 H 0.0003 0.7591 0.7084 0.019 Uiso 1 1 calc R . . C16 C 0.2767(2) 0.67518(7) 1.05403(10) 0.0162(2) Uani 1 1 d . . . H16A H 0.2731 0.7253 1.0445 0.019 Uiso 1 1 calc R . . H16B H 0.3212 0.6665 1.1177 0.019 Uiso 1 1 calc R . . C17 C 0.0663(2) 0.64608(10) 1.03786(13) 0.0277(3) Uani 1 1 d . . . H17A H 0.0213 0.6551 0.9750 0.041 Uiso 1 1 calc R . . H17B H -0.0275 0.6677 1.0795 0.041 Uiso 1 1 calc R . . H17C H 0.0690 0.5966 1.0486 0.041 Uiso 1 1 calc R . . C18 C 0.4794(2) 0.81050(8) 0.92134(10) 0.0183(2) Uani 1 1 d . . . H18A H 0.4897 0.7886 0.9819 0.022 Uiso 1 1 calc R . . H18B H 0.4336 0.8582 0.9298 0.022 Uiso 1 1 calc R . . C19 C 0.6849(3) 0.81090(10) 0.87979(13) 0.0287(4) Uani 1 1 d . . . H19A H 0.7307 0.7638 0.8712 0.043 Uiso 1 1 calc R . . H19B H 0.7813 0.8350 0.9202 0.043 Uiso 1 1 calc R . . H19C H 0.6765 0.8342 0.8209 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rh1 0.01232(4) 0.01250(4) 0.01203(4) 0.00034(3) 0.00155(3) 0.00083(3) Rh2 0.01171(4) 0.01163(4) 0.01330(4) 0.00002(3) 0.00021(3) -0.00106(3) Cl1 0.02869(16) 0.01408(13) 0.01928(15) 0.00049(11) 0.00615(12) 0.00216(12) Cl2 0.02419(15) 0.02034(15) 0.01559(14) 0.00190(11) -0.00024(11) -0.00504(12) O1 0.0227(5) 0.0218(5) 0.0219(5) 0.0032(4) -0.0006(4) 0.0004(4) O2 0.0303(6) 0.0273(6) 0.0173(5) -0.0035(4) 0.0032(4) -0.0030(5) O3 0.0236(5) 0.0187(5) 0.0249(6) 0.0021(4) 0.0022(4) -0.0003(4) O4 0.0328(6) 0.0217(6) 0.0322(7) -0.0108(5) 0.0044(5) -0.0028(5) N1 0.0131(4) 0.0120(4) 0.0137(5) 0.0000(4) 0.0010(3) 0.0009(3) N2 0.0144(4) 0.0139(5) 0.0126(4) -0.0010(4) 0.0013(4) -0.0005(4) N3 0.0125(4) 0.0124(4) 0.0146(5) 0.0007(4) 0.0008(4) 0.0003(3) N4 0.0150(4) 0.0108(4) 0.0171(5) -0.0016(4) 0.0017(4) -0.0009(3) C1 0.0139(5) 0.0206(6) 0.0148(5) -0.0012(5) 0.0005(4) 0.0002(4) C2 0.0172(5) 0.0167(6) 0.0170(6) 0.0007(5) 0.0017(4) -0.0006(4) C3 0.0139(5) 0.0147(5) 0.0212(6) -0.0039(5) 0.0006(4) -0.0006(4) C4 0.0173(5) 0.0179(6) 0.0205(6) -0.0016(5) 0.0024(5) -0.0010(5) C10 0.0144(5) 0.0153(5) 0.0150(5) 0.0011(4) -0.0005(4) 0.0016(4) C11 0.0161(5) 0.0164(6) 0.0139(5) 0.0017(4) -0.0009(4) 0.0005(4) C12 0.0124(4) 0.0115(5) 0.0129(5) -0.0004(4) 0.0002(4) -0.0001(4) C13 0.0129(5) 0.0108(5) 0.0129(5) -0.0004(4) 0.0013(4) -0.0003(4) C14 0.0174(5) 0.0120(5) 0.0213(6) 0.0014(5) 0.0023(5) 0.0016(4) C15 0.0152(5) 0.0139(5) 0.0183(6) 0.0032(4) 0.0007(4) 0.0020(4) C16 0.0165(5) 0.0171(6) 0.0152(5) -0.0043(4) 0.0039(4) -0.0020(4) C17 0.0203(6) 0.0324(9) 0.0308(8) -0.0138(7) 0.0089(6) -0.0081(6) C18 0.0192(6) 0.0162(6) 0.0197(6) -0.0056(5) 0.0032(5) -0.0049(5) C19 0.0203(6) 0.0365(9) 0.0294(8) -0.0110(7) 0.0045(6) -0.0094(6) _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 Rh1 C1 1.8469(16) . yes Rh1 C2 1.8586(15) . yes Rh1 N1 2.1053(12) . yes Rh1 Cl1 2.3865(6) . yes Rh1 Rh2 3.1781(5) . yes Rh2 C3 1.8488(16) . yes Rh2 C4 1.8656(15) . yes Rh2 N3 2.1140(12) . yes Rh2 Cl2 2.3705(5) . yes Rh2 Rh1 3.4345(6) 1_455 yes O1 C1 1.1315(19) . ? O2 C2 1.1360(18) . ? O3 C3 1.1252(19) . ? O4 C4 1.1376(19) . ? N1 C12 1.3360(17) . ? N1 C10 1.3826(18) . ? N2 C12 1.3537(17) . ? N2 C11 1.3764(18) . ? N2 C16 1.4719(17) . ? N3 C13 1.3459(17) . ? N3 C15 1.3828(18) . ? N4 C13 1.3591(17) . ? N4 C14 1.3803(19) . ? N4 C18 1.4803(19) . ? C10 C11 1.3588(19) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.4612(18) . ? C14 C15 1.366(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.514(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.504(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? 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 Rh1 C2 88.41(6) . . yes C1 Rh1 N1 94.28(5) . . ? C2 Rh1 N1 176.88(5) . . ? C1 Rh1 Cl1 176.26(4) . . ? C2 Rh1 Cl1 88.06(5) . . ? N1 Rh1 Cl1 89.28(3) . . yes C1 Rh1 Rh2 88.58(4) . . ? C2 Rh1 Rh2 95.85(4) . . ? N1 Rh1 Rh2 82.65(3) . . ? Cl1 Rh1 Rh2 93.018(10) . . ? C3 Rh2 C4 88.38(7) . . yes C3 Rh2 N3 94.10(6) . . ? C4 Rh2 N3 176.94(6) . . ? C3 Rh2 Cl2 176.33(4) . . ? C4 Rh2 Cl2 88.48(5) . . ? N3 Rh2 Cl2 89.10(4) . . yes C3 Rh2 Rh1 86.75(4) . . ? C4 Rh2 Rh1 96.49(5) . . ? N3 Rh2 Rh1 81.88(3) . . ? Cl2 Rh2 Rh1 95.481(12) . . ? C3 Rh2 Rh1 87.85(4) . 1_455 ? C4 Rh2 Rh1 81.19(4) . 1_455 ? N3 Rh2 Rh1 100.68(3) . 1_455 ? Cl2 Rh2 Rh1 89.801(11) . 1_455 ? Rh1 Rh2 Rh1 174.184(5) . 1_455 yes C12 N1 C10 106.33(11) . . ? C12 N1 Rh1 127.09(9) . . ? C10 N1 Rh1 125.54(9) . . ? C12 N2 C11 107.80(11) . . ? C12 N2 C16 127.08(12) . . ? C11 N2 C16 124.33(12) . . ? C13 N3 C15 106.04(11) . . ? C13 N3 Rh2 127.55(9) . . ? C15 N3 Rh2 125.78(10) . . ? C13 N4 C14 107.47(12) . . ? C13 N4 C18 127.33(12) . . ? C14 N4 C18 124.55(12) . . ? O1 C1 Rh1 176.94(13) . . ? O2 C2 Rh1 179.26(14) . . ? O3 C3 Rh2 177.52(13) . . ? O4 C4 Rh2 179.39(15) . . ? C11 C10 N1 109.24(12) . . ? C11 C10 H10 125.4 . . ? N1 C10 H10 125.4 . . ? C10 C11 N2 106.49(12) . . ? C10 C11 H11 126.8 . . ? N2 C11 H11 126.8 . . ? N1 C12 N2 110.14(11) . . ? N1 C12 C13 125.64(12) . . ? N2 C12 C13 124.20(11) . . ? N3 C13 N4 110.43(11) . . ? N3 C13 C12 125.07(12) . . ? N4 C13 C12 124.50(12) . . ? C15 C14 N4 106.65(12) . . ? C15 C14 H14 126.7 . . ? N4 C14 H14 126.7 . . ? C14 C15 N3 109.41(13) . . ? C14 C15 H15 125.3 . . ? N3 C15 H15 125.3 . . ? N2 C16 C17 111.37(12) . . ? N2 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? N2 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 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 . . ? N4 C18 C19 111.93(12) . . ? N4 C18 H18A 109.2 . . ? C19 C18 H18A 109.2 . . ? N4 C18 H18B 109.2 . . ? C19 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 36.60 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.964 _refine_diff_density_min -0.794 _refine_diff_density_rms 0.104 #===END======================================================================== data_1b _database_code_depnum_ccdc_archive 'CCDC 872000' #TrackingRef 'Laurila.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 Cl2 N4 O4 Rh2' _chemical_formula_sum 'C14 H14 Cl2 N4 O4 Rh2' _chemical_formula_weight 579.01 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _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 6.6991(9) _cell_length_b 19.587(3) _cell_length_c 14.9395(19) _cell_angle_alpha 90.00 _cell_angle_beta 91.815(5) _cell_angle_gamma 90.00 _cell_volume 1959.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 260(2) _cell_measurement_reflns_used 9971 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 30.55 _exptl_crystal_description block _exptl_crystal_colour 'green with metallic shine' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.963 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 1.983 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5187 _exptl_absorpt_correction_T_max 0.7882 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _publ_section_exptl_refinement ; The hydrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C---H = 0.93-0.97 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 1.47 \%A from atom H15 and the deepest hole is located 1.87 \%A from atom Cl1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 260(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'curved graphite crystal' _diffrn_measurement_device_type 'Bruker KAPPA APEX II DUO CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_reflns_number 20729 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 30.65 _reflns_number_total 5978 _reflns_number_gt 4869 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2g (Brandenburg, 2011)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0111P)^2^+2.8448P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5978 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0580 _refine_ls_wR_factor_gt 0.0507 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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 Rh1 Rh 0.60313(3) 0.588115(9) 0.730132(12) 0.03069(5) Uani 1 1 d . . . Rh2 Rh 0.12426(3) 0.595324(9) 0.722888(13) 0.03062(5) Uani 1 1 d . . . Cl1 Cl 0.60569(12) 0.46986(3) 0.76466(5) 0.05015(17) Uani 1 1 d . . . Cl2 Cl 0.10027(12) 0.65133(4) 0.58260(5) 0.04960(17) Uani 1 1 d . . . O1 O 0.6153(3) 0.73227(11) 0.67203(15) 0.0523(5) Uani 1 1 d . . . O2 O 0.6419(4) 0.55009(13) 0.53792(14) 0.0639(6) Uani 1 1 d . . . O3 O 0.1328(3) 0.51584(11) 0.89168(15) 0.0525(5) Uani 1 1 d . . . O4 O 0.0596(4) 0.46401(12) 0.62534(18) 0.0711(7) Uani 1 1 d . . . N1 N 0.5627(3) 0.60968(10) 0.86698(13) 0.0301(4) Uani 1 1 d . . . N2 N 0.4227(3) 0.64447(10) 0.99089(13) 0.0328(4) Uani 1 1 d . . . N3 N 0.1814(3) 0.69039(10) 0.78548(13) 0.0305(4) Uani 1 1 d . . . N4 N 0.3324(3) 0.77261(10) 0.86316(14) 0.0349(4) Uani 1 1 d . . . C1 C 0.6101(4) 0.67868(14) 0.69618(17) 0.0372(5) Uani 1 1 d . . . C2 C 0.6291(4) 0.56466(14) 0.61067(18) 0.0405(6) Uani 1 1 d . . . C3 C 0.1303(4) 0.54692(13) 0.82965(19) 0.0366(5) Uani 1 1 d . . . C4 C 0.0830(4) 0.51345(14) 0.6627(2) 0.0433(6) Uani 1 1 d . . . C10 C 0.6368(4) 0.57163(13) 0.93785(16) 0.0354(5) Uani 1 1 d . . . H10 H 0.7306 0.5368 0.9340 0.043 Uiso 1 1 calc R . . C11 C 0.5517(4) 0.59271(13) 1.01455(17) 0.0380(5) Uani 1 1 d . . . H11 H 0.5762 0.5754 1.0718 0.046 Uiso 1 1 calc R . . C12 C 0.4331(3) 0.65363(11) 0.90122(15) 0.0282(4) Uani 1 1 d . . . C13 C 0.3174(3) 0.70420(11) 0.85046(16) 0.0293(4) Uani 1 1 d . . . C14 C 0.1994(4) 0.80305(13) 0.80382(19) 0.0408(6) Uani 1 1 d . . . H14 H 0.1768 0.8497 0.7973 0.049 Uiso 1 1 calc R . . C15 C 0.1075(4) 0.75256(13) 0.75664(19) 0.0384(5) Uani 1 1 d . . . H15 H 0.0097 0.7588 0.7118 0.046 Uiso 1 1 calc R . . C16 C 0.2788(4) 0.67579(14) 1.05159(18) 0.0407(6) Uani 1 1 d . . . H16A H 0.2698 0.7243 1.0392 0.049 Uiso 1 1 calc R . . H16B H 0.3277 0.6703 1.1130 0.049 Uiso 1 1 calc R . . C17 C 0.0767(5) 0.6451(2) 1.0419(3) 0.0753(12) Uani 1 1 d . . . H17A H 0.0257 0.6517 0.9818 0.113 Uiso 1 1 calc R . . H17B H -0.0108 0.6666 1.0830 0.113 Uiso 1 1 calc R . . H17C H 0.0845 0.5971 1.0547 0.113 Uiso 1 1 calc R . . C18 C 0.4804(4) 0.80958(14) 0.9205(2) 0.0455(6) Uani 1 1 d . . . H18A H 0.4353 0.8562 0.9285 0.055 Uiso 1 1 calc R . . H18B H 0.4884 0.7881 0.9790 0.055 Uiso 1 1 calc R . . C19 C 0.6801(5) 0.8106(2) 0.8828(3) 0.0877(14) Uani 1 1 d . . . H19A H 0.7278 0.7646 0.8769 0.132 Uiso 1 1 calc R . . H19B H 0.7697 0.8357 0.9220 0.132 Uiso 1 1 calc R . . H19C H 0.6734 0.8320 0.8251 0.132 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rh1 0.03028(9) 0.03148(9) 0.03049(9) 0.00084(7) 0.00384(7) 0.00197(7) Rh2 0.02896(9) 0.02800(9) 0.03486(10) 0.00035(7) 0.00058(7) -0.00294(7) Cl1 0.0701(5) 0.0328(3) 0.0484(4) 0.0004(3) 0.0145(3) 0.0054(3) Cl2 0.0594(4) 0.0506(4) 0.0387(3) 0.0057(3) -0.0004(3) -0.0119(3) O1 0.0557(13) 0.0434(11) 0.0577(13) 0.0132(10) -0.0001(10) -0.0001(9) O2 0.0775(16) 0.0740(16) 0.0406(12) -0.0123(11) 0.0082(11) -0.0077(13) O3 0.0602(13) 0.0441(11) 0.0535(12) 0.0114(10) 0.0040(10) -0.0029(10) O4 0.0822(18) 0.0523(14) 0.0790(17) -0.0303(13) 0.0068(14) -0.0079(12) N1 0.0286(9) 0.0302(9) 0.0314(10) 0.0001(8) 0.0018(7) 0.0009(7) N2 0.0355(10) 0.0326(10) 0.0303(10) -0.0023(8) 0.0016(8) -0.0024(8) N3 0.0298(9) 0.0246(9) 0.0372(10) 0.0013(8) 0.0040(8) -0.0004(7) N4 0.0366(10) 0.0255(9) 0.0429(11) -0.0037(8) 0.0063(9) -0.0029(8) C1 0.0335(12) 0.0436(14) 0.0346(12) -0.0017(11) 0.0028(10) -0.0001(10) C2 0.0412(14) 0.0429(14) 0.0377(13) -0.0006(11) 0.0046(11) -0.0005(11) C3 0.0319(12) 0.0304(12) 0.0476(14) -0.0026(11) 0.0026(10) -0.0028(9) C4 0.0403(14) 0.0395(14) 0.0501(16) -0.0053(12) 0.0034(12) -0.0031(11) C10 0.0340(12) 0.0360(12) 0.0360(12) 0.0024(10) -0.0025(10) 0.0046(10) C11 0.0408(13) 0.0421(14) 0.0308(12) 0.0050(10) -0.0031(10) -0.0017(11) C12 0.0287(10) 0.0262(10) 0.0297(10) -0.0024(8) 0.0010(8) -0.0042(8) C13 0.0291(10) 0.0255(10) 0.0335(11) -0.0010(9) 0.0049(9) -0.0010(8) C14 0.0444(14) 0.0262(11) 0.0523(16) 0.0031(11) 0.0093(12) 0.0036(10) C15 0.0357(13) 0.0321(12) 0.0474(14) 0.0073(11) 0.0025(11) 0.0038(10) C16 0.0441(14) 0.0427(14) 0.0359(13) -0.0103(11) 0.0103(11) -0.0056(11) C17 0.0470(18) 0.089(3) 0.092(3) -0.046(2) 0.0256(18) -0.0204(18) C18 0.0500(16) 0.0368(14) 0.0499(16) -0.0139(12) 0.0075(13) -0.0136(12) C19 0.051(2) 0.115(4) 0.098(3) -0.050(3) 0.011(2) -0.029(2) _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 Rh1 C1 1.846(3) . yes Rh1 C2 1.856(3) . yes Rh1 N1 2.1134(19) . yes Rh1 Cl1 2.3731(8) . yes Rh1 Rh2 3.2095(5) . yes Rh2 C3 1.855(3) . yes Rh2 C4 1.855(3) . yes Rh2 N3 2.1133(19) . yes Rh2 Cl2 2.3665(8) . yes Rh2 Rh1 3.4990(5) 1_455 yes O1 C1 1.111(3) . ? O2 C2 1.130(3) . ? O3 C3 1.108(3) . ? O4 C4 1.126(3) . ? N1 C12 1.336(3) . ? N1 C10 1.375(3) . ? N2 C12 1.356(3) . ? N2 C11 1.371(3) . ? N2 C16 1.477(3) . ? N3 C13 1.338(3) . ? N3 C15 1.379(3) . ? N4 C13 1.357(3) . ? N4 C14 1.373(3) . ? N4 C18 1.479(3) . ? C10 C11 1.360(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.456(3) . ? C14 C15 1.351(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.484(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.467(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 Rh1 C2 88.26(12) . . yes C1 Rh1 N1 94.52(9) . . ? C2 Rh1 N1 176.61(10) . . ? C1 Rh1 Cl1 176.07(8) . . ? C2 Rh1 Cl1 88.12(9) . . ? N1 Rh1 Cl1 89.14(6) . . yes C1 Rh1 Rh2 89.00(8) . . ? C2 Rh1 Rh2 95.89(9) . . ? N1 Rh1 Rh2 82.26(5) . . ? Cl1 Rh1 Rh2 92.90(2) . . ? C3 Rh2 C4 88.51(12) . . yes C3 Rh2 N3 94.08(9) . . ? C4 Rh2 N3 176.76(10) . . ? C3 Rh2 Cl2 175.97(8) . . ? C4 Rh2 Cl2 88.08(9) . . ? N3 Rh2 Cl2 89.40(6) . . yes C3 Rh2 Rh1 87.35(8) . . ? C4 Rh2 Rh1 96.42(9) . . ? N3 Rh2 Rh1 81.77(5) . . ? Cl2 Rh2 Rh1 95.17(2) . . ? C3 Rh2 Rh1 86.99(8) . 1_455 ? C4 Rh2 Rh1 81.17(9) . 1_455 ? N3 Rh2 Rh1 100.89(5) . 1_455 ? Cl2 Rh2 Rh1 90.36(2) . 1_455 ? Rh1 Rh2 Rh1 173.909(9) . 1_455 yes C12 N1 C10 106.1(2) . . ? C12 N1 Rh1 127.15(16) . . ? C10 N1 Rh1 125.64(16) . . ? C12 N2 C11 107.5(2) . . ? C12 N2 C16 127.4(2) . . ? C11 N2 C16 124.5(2) . . ? C13 N3 C15 106.1(2) . . ? C13 N3 Rh2 127.52(15) . . ? C15 N3 Rh2 125.58(17) . . ? C13 N4 C14 107.2(2) . . ? C13 N4 C18 127.6(2) . . ? C14 N4 C18 124.8(2) . . ? O1 C1 Rh1 177.0(2) . . ? O2 C2 Rh1 178.9(3) . . ? O3 C3 Rh2 177.4(2) . . ? O4 C4 Rh2 179.1(3) . . ? C11 C10 N1 109.5(2) . . ? C11 C10 H10 125.3 . . ? N1 C10 H10 125.3 . . ? C10 C11 N2 106.5(2) . . ? C10 C11 H11 126.7 . . ? N2 C11 H11 126.7 . . ? N1 C12 N2 110.3(2) . . ? N1 C12 C13 125.5(2) . . ? N2 C12 C13 124.2(2) . . ? N3 C13 N4 110.3(2) . . ? N3 C13 C12 125.4(2) . . ? N4 C13 C12 124.3(2) . . ? C15 C14 N4 107.1(2) . . ? C15 C14 H14 126.4 . . ? N4 C14 H14 126.4 . . ? C14 C15 N3 109.3(2) . . ? C14 C15 H15 125.4 . . ? N3 C15 H15 125.4 . . ? N2 C16 C17 112.5(2) . . ? N2 C16 H16A 109.1 . . ? C17 C16 H16A 109.1 . . ? N2 C16 H16B 109.1 . . ? C17 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? 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 . . ? C19 C18 N4 112.8(2) . . ? C19 C18 H18A 109.0 . . ? N4 C18 H18A 109.0 . . ? C19 C18 H18B 109.0 . . ? N4 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 30.65 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.948 _refine_diff_density_min -0.624 _refine_diff_density_rms 0.083 #===END======================================================================== data_2 _database_code_depnum_ccdc_archive 'CCDC 872001' #TrackingRef 'Laurila.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 Cl2 N4 O4 Rh2' _chemical_formula_sum 'C16 H18 Cl2 N4 O4 Rh2' _chemical_formula_weight 607.06 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 6.58710(10) _cell_length_b 20.6666(5) _cell_length_c 15.7822(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.0130(10) _cell_angle_gamma 90.00 _cell_volume 2115.75(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9915 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 38.95 _exptl_crystal_description block _exptl_crystal_colour 'purple with green metallic lustre' _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.906 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 1.841 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6009 _exptl_absorpt_correction_T_max 0.7958 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _publ_section_exptl_refinement ; The hydrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C---H = 0.95-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.85 \%A from atom Rh1 and the deepest hole is located 0.56 \%A from atom Rh1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'flat graphite crystal' _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on three-circle goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans' _diffrn_reflns_number 13858 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2439 _reflns_number_gt 2158 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2g (Brandenburg, 2011)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0179P)^2^+6.4331P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2439 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0284 _refine_ls_R_factor_gt 0.0238 _refine_ls_wR_factor_ref 0.0579 _refine_ls_wR_factor_gt 0.0556 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Rh1 Rh 0.23907(3) 0.154591(9) 0.250505(14) 0.02938(8) Uani 1 1 d . . . Cl1 Cl 0.30656(11) 0.10414(4) 0.38736(6) 0.04526(19) Uani 1 1 d . . . O1 O 0.1533(3) 0.20903(10) 0.07339(14) 0.0387(5) Uani 1 1 d . . . O2 O 0.2553(3) 0.02221(10) 0.1774(2) 0.0650(8) Uani 1 1 d . . . N1 N 0.2173(3) 0.24418(10) 0.31111(14) 0.0280(4) Uani 1 1 d . . . N2 N 0.0956(3) 0.33664(10) 0.35081(14) 0.0311(5) Uani 1 1 d . . . C1 C 0.1874(4) 0.18934(12) 0.1415(2) 0.0313(6) Uani 1 1 d . . . C2 C 0.2511(4) 0.07307(14) 0.2037(3) 0.0446(8) Uani 1 1 d . . . C5 C 0.3267(4) 0.26198(14) 0.39019(18) 0.0336(6) Uani 1 1 d . . . H5 H 0.4371 0.2381 0.4223 0.040 Uiso 1 1 calc R . . C6 C 0.2534(4) 0.31832(14) 0.41489(18) 0.0354(6) Uani 1 1 d . . . H6 H 0.3016 0.3411 0.4668 0.043 Uiso 1 1 calc R . . C7 C -0.0450(6) 0.39153(14) 0.3578(2) 0.0452(7) Uani 1 1 d . . . H7A H -0.1148 0.4040 0.2994 0.054 Uiso 1 1 calc R . . H7B H 0.0372 0.4291 0.3832 0.054 Uiso 1 1 calc R . . C8 C -0.2039(5) 0.37618(16) 0.4114(3) 0.0636(11) Uani 1 1 d . . . H8A H -0.1348 0.3600 0.4682 0.076 Uiso 1 1 calc R . . H8B H -0.2946 0.3414 0.3832 0.076 Uiso 1 1 calc R . . C9 C -0.3337(6) 0.43432(17) 0.4245(4) 0.0844(16) Uani 1 1 d . . . H9A H -0.2441 0.4695 0.4506 0.127 Uiso 1 1 calc R . . H9B H -0.4306 0.4227 0.4626 0.127 Uiso 1 1 calc R . . H9C H -0.4105 0.4486 0.3688 0.127 Uiso 1 1 calc R . . C10 C 0.0772(4) 0.29080(11) 0.28902(16) 0.0273(5) Uani 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 Rh1 0.01484(10) 0.01741(11) 0.05435(15) 0.00354(9) 0.00172(8) 0.00030(7) Cl1 0.0313(3) 0.0351(4) 0.0711(5) 0.0238(4) 0.0137(3) 0.0073(3) O1 0.0320(10) 0.0341(11) 0.0473(12) -0.0098(9) -0.0003(8) 0.0057(8) O2 0.0373(12) 0.0238(11) 0.136(3) -0.0156(14) 0.0202(14) 0.0008(9) N1 0.0193(9) 0.0223(10) 0.0397(12) 0.0060(9) -0.0025(8) -0.0040(8) N2 0.0367(12) 0.0198(10) 0.0350(12) 0.0007(9) 0.0015(9) -0.0081(9) C1 0.0178(11) 0.0209(12) 0.0525(17) -0.0096(12) -0.0008(11) 0.0019(9) C2 0.0181(12) 0.0250(14) 0.091(3) 0.0006(15) 0.0088(13) 0.0013(10) C5 0.0216(11) 0.0382(15) 0.0380(14) 0.0093(12) -0.0029(10) -0.0097(10) C6 0.0330(13) 0.0361(15) 0.0345(14) 0.0031(12) -0.0020(11) -0.0152(12) C7 0.071(2) 0.0214(14) 0.0426(17) 0.0012(12) 0.0068(15) -0.0028(14) C8 0.0294(15) 0.0341(18) 0.128(4) 0.026(2) 0.0149(18) 0.0011(13) C9 0.052(2) 0.0283(18) 0.177(5) 0.026(2) 0.031(3) 0.0042(16) C10 0.0275(12) 0.0166(11) 0.0356(14) 0.0011(10) -0.0004(10) -0.0050(9) _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 Rh1 C1 1.840(3) . yes Rh1 C2 1.847(3) . yes Rh1 N1 2.100(2) . yes Rh1 Cl1 2.3697(8) . yes Rh1 Rh1 3.1469(3) 2 yes Rh1 Rh1 3.4403(3) 2_655 yes O1 C1 1.135(3) . ? O2 C2 1.132(4) . ? N1 C10 1.338(3) . ? N1 C5 1.378(3) . ? N2 C10 1.350(3) . ? N2 C6 1.371(3) . ? N2 C7 1.480(4) . ? C5 C6 1.344(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.490(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.509(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C10 1.455(5) 2 ? 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 Rh1 C2 89.77(14) . . yes C1 Rh1 N1 93.76(10) . . yes C2 Rh1 N1 175.89(12) . . ? C1 Rh1 Cl1 176.84(8) . . ? C2 Rh1 Cl1 87.07(12) . . yes N1 Rh1 Cl1 89.41(6) . . yes C1 Rh1 Rh1 88.46(7) . 2 ? C2 Rh1 Rh1 96.35(8) . 2 ? N1 Rh1 Rh1 81.66(5) . 2 ? Cl1 Rh1 Rh1 91.926(19) . 2 ? C1 Rh1 Rh1 91.04(7) . 2_655 ? C2 Rh1 Rh1 83.43(8) . 2_655 ? N1 Rh1 Rh1 98.59(5) . 2_655 ? Cl1 Rh1 Rh1 88.565(18) . 2_655 ? Rh1 Rh1 Rh1 179.453(16) 2 2_655 ? C10 N1 C5 105.8(2) . . ? C10 N1 Rh1 127.93(17) . . ? C5 N1 Rh1 125.56(18) . . ? C10 N2 C6 107.5(2) . . ? C10 N2 C7 127.8(2) . . ? C6 N2 C7 124.1(2) . . ? O1 C1 Rh1 177.9(2) . . ? O2 C2 Rh1 177.5(3) . . ? C6 C5 N1 109.7(2) . . ? C6 C5 H5 125.2 . . ? N1 C5 H5 125.2 . . ? C5 C6 N2 106.8(2) . . ? C5 C6 H6 126.6 . . ? N2 C6 H6 126.6 . . ? N2 C7 C8 112.9(2) . . ? N2 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N2 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 C9 112.3(3) . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? C7 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 N2 110.2(2) . . ? N1 C10 C10 124.7(2) . 2 ? N2 C10 C10 124.99(19) . 2 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.879 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.076 #===END======================================================================== data_2b _database_code_depnum_ccdc_archive 'CCDC 872002' #TrackingRef 'Laurila.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 Cl2 N4 O4 Rh2' _chemical_formula_sum 'C16 H18 Cl2 N4 O4 Rh2' _chemical_formula_weight 607.06 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 6.6678(10) _cell_length_b 20.686(4) _cell_length_c 15.926(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.359(9) _cell_angle_gamma 90.00 _cell_volume 2160.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 260(2) _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 32.75 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.866 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 1.803 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5817 _exptl_absorpt_correction_T_max 0.8531 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _publ_section_exptl_refinement ; The hydrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C---H = 0.95-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.79 \%A from atom Rh1 and the deepest hole is located 0.54 \%A from atom Rh1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 260(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'curved graphite crystal' _diffrn_measurement_device_type 'Bruker KAPPA APEX II DUO CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_reflns_number 14458 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 31.00 _reflns_number_total 3448 _reflns_number_gt 2798 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2g (Brandenburg, 2011)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0282P)^2^+2.2595P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3448 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0649 _refine_ls_wR_factor_gt 0.0588 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Rh1 Rh 0.23841(2) 0.155571(8) 0.251031(9) 0.03371(6) Uani 1 1 d . . . Cl1 Cl 0.30625(11) 0.10591(3) 0.38686(4) 0.05458(15) Uani 1 1 d . . . O1 O 0.1560(3) 0.20835(9) 0.07436(11) 0.0553(4) Uani 1 1 d . . . O2 O 0.2567(3) 0.02385(10) 0.17969(16) 0.0772(6) Uani 1 1 d . . . N1 N 0.2159(2) 0.24509(8) 0.31094(10) 0.0339(3) Uani 1 1 d . . . N2 N 0.0923(3) 0.33645(8) 0.35073(11) 0.0396(4) Uani 1 1 d . . . C1 C 0.1885(3) 0.18940(11) 0.14240(14) 0.0391(4) Uani 1 1 d . . . C2 C 0.2510(3) 0.07444(12) 0.20507(17) 0.0476(5) Uani 1 1 d . . . C5 C 0.3239(3) 0.26267(12) 0.38935(13) 0.0417(5) Uani 1 1 d . . . H5 H 0.4320 0.2396 0.4205 0.050 Uiso 1 1 calc R . . C6 C 0.2492(4) 0.31839(12) 0.41413(14) 0.0462(5) Uani 1 1 d . . . H6 H 0.2953 0.3405 0.4648 0.055 Uiso 1 1 calc R . . C7 C -0.0458(4) 0.39080(11) 0.35679(17) 0.0522(6) Uani 1 1 d . . . H7A H -0.1114 0.4032 0.2997 0.063 Uiso 1 1 calc R . . H7B H 0.0337 0.4274 0.3821 0.063 Uiso 1 1 calc R . . C8 C -0.2048(4) 0.37615(15) 0.4079(3) 0.0729(9) Uani 1 1 d . . . H8A H -0.1399 0.3609 0.4638 0.088 Uiso 1 1 calc R . . H8B H -0.2909 0.3417 0.3803 0.088 Uiso 1 1 calc R . . C9 C -0.3355(6) 0.43375(17) 0.4186(3) 0.1072(16) Uani 1 1 d . . . H9A H -0.2503 0.4689 0.4428 0.161 Uiso 1 1 calc R . . H9B H -0.4284 0.4227 0.4559 0.161 Uiso 1 1 calc R . . H9C H -0.4111 0.4464 0.3640 0.161 Uiso 1 1 calc R . . C10 C 0.0762(3) 0.29084(9) 0.28891(12) 0.0333(4) Uani 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 Rh1 0.03019(8) 0.03306(9) 0.03766(9) -0.00244(6) 0.00548(6) 0.00162(5) Cl1 0.0658(4) 0.0491(3) 0.0487(3) 0.0104(3) 0.0098(3) 0.0081(3) O1 0.0652(11) 0.0621(11) 0.0398(9) 0.0004(8) 0.0126(8) 0.0054(9) O2 0.0726(13) 0.0445(11) 0.1138(19) -0.0250(12) 0.0146(12) 0.0028(9) N1 0.0326(7) 0.0351(9) 0.0336(8) -0.0018(7) 0.0049(6) -0.0031(6) N2 0.0500(9) 0.0326(9) 0.0383(9) -0.0048(7) 0.0137(7) -0.0050(7) C1 0.0364(9) 0.0399(11) 0.0423(11) -0.0109(9) 0.0101(8) -0.0007(8) C2 0.0385(10) 0.0446(13) 0.0588(15) -0.0056(11) 0.0063(9) 0.0036(9) C5 0.0363(9) 0.0506(13) 0.0367(10) -0.0039(9) 0.0024(8) -0.0075(9) C6 0.0519(12) 0.0470(13) 0.0390(11) -0.0102(10) 0.0065(9) -0.0137(10) C7 0.0775(17) 0.0308(11) 0.0540(14) -0.0030(10) 0.0272(13) 0.0008(11) C8 0.0555(15) 0.0487(16) 0.123(3) 0.0190(17) 0.0379(17) 0.0060(12) C9 0.093(3) 0.0489(18) 0.199(5) 0.010(2) 0.077(3) 0.0107(17) C10 0.0378(9) 0.0282(9) 0.0353(9) -0.0010(7) 0.0099(7) -0.0039(7) _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 Rh1 C2 1.839(3) . yes Rh1 C1 1.840(2) . yes Rh1 N1 2.1008(17) . yes Rh1 Cl1 2.3637(7) . yes Rh1 Rh1 3.1737(5) 2 yes Rh1 Rh1 3.4944(6) 2_655 yes O1 C1 1.136(3) . ? O2 C2 1.125(3) . ? N1 C10 1.330(3) . ? N1 C5 1.374(3) . ? N2 C10 1.354(2) . ? N2 C6 1.369(3) . ? N2 C7 1.467(3) . ? C5 C6 1.343(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.479(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.504(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C10 1.455(4) 2 ? 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 C2 Rh1 C1 89.21(11) . . yes C2 Rh1 N1 175.81(9) . . ? C1 Rh1 N1 94.37(8) . . ? C2 Rh1 Cl1 87.29(9) . . ? C1 Rh1 Cl1 176.48(7) . . ? N1 Rh1 Cl1 89.14(5) . . yes C2 Rh1 Rh1 96.49(7) . 2 ? C1 Rh1 Rh1 88.79(6) . 2 ? N1 Rh1 Rh1 81.45(4) . 2 ? Cl1 Rh1 Rh1 92.06(2) . 2 ? C2 Rh1 Rh1 83.07(7) . 2_655 ? C1 Rh1 Rh1 90.18(6) . 2_655 ? N1 Rh1 Rh1 99.06(4) . 2_655 ? Cl1 Rh1 Rh1 88.942(19) . 2_655 ? Rh1 Rh1 Rh1 178.888(10) 2 2_655 yes C10 N1 C5 106.21(17) . . ? C10 N1 Rh1 127.69(13) . . ? C5 N1 Rh1 125.28(15) . . ? C10 N2 C6 107.23(18) . . ? C10 N2 C7 127.8(2) . . ? C6 N2 C7 124.5(2) . . ? O1 C1 Rh1 177.8(2) . . ? O2 C2 Rh1 177.4(3) . . ? C6 C5 N1 109.4(2) . . ? C6 C5 H5 125.3 . . ? N1 C5 H5 125.3 . . ? C5 C6 N2 106.99(19) . . ? C5 C6 H6 126.5 . . ? N2 C6 H6 126.5 . . ? N2 C7 C8 113.5(2) . . ? N2 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? N2 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C9 112.8(3) . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 N2 110.13(18) . . ? N1 C10 C10 125.01(14) . 2 ? N2 C10 C10 124.83(15) . 2 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.562 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.076 #===END======================================================================== data_2c _database_code_depnum_ccdc_archive 'CCDC 872003' #TrackingRef 'Laurila.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 Cl2 N4 O4 Rh2' _chemical_formula_sum 'C16 H18 Cl2 N4 O4 Rh2' _chemical_formula_weight 607.06 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.5663(5) _cell_length_b 20.5989(18) _cell_length_c 15.7624(12) _cell_angle_alpha 90.00 _cell_angle_beta 100.392(4) _cell_angle_gamma 90.00 _cell_volume 2097.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 88(2) _cell_measurement_reflns_used 9885 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 35.16 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.923 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 1.858 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5896 _exptl_absorpt_correction_T_max 0.8872 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _publ_section_exptl_refinement ; Hydrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C---H = 0.95-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.71 \%A from atom Rh1 and the deepest hole is located 0.68 \%A from atom Rh2. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 88(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'curved graphite crystal' _diffrn_measurement_device_type 'Bruker KAPPA APEX II DUO CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_reflns_number 22248 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28.50 _reflns_number_total 5289 _reflns_number_gt 4585 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2g (Brandenburg, 2011)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0000P)^2^+19.0713P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5289 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0942 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.159 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Rh1 Rh 0.74147(5) 0.152451(16) 0.72914(2) 0.01385(9) Uani 1 1 d . . . Rh2 Rh 0.26325(5) 0.156106(16) 0.72968(2) 0.01295(8) Uani 1 1 d . . . Cl1 Cl 0.79864(18) 0.09703(6) 0.86290(8) 0.0226(2) Uani 1 1 d . . . Cl2 Cl 0.18600(17) 0.10914(6) 0.59077(7) 0.0203(2) Uani 1 1 d . . . O1 O 0.6650(5) 0.21382(17) 0.5556(2) 0.0205(7) Uani 1 1 d . . . O2 O 0.7424(6) 0.02307(18) 0.6444(3) 0.0338(9) Uani 1 1 d . . . O3 O 0.3623(5) 0.20493(17) 0.9104(2) 0.0215(7) Uani 1 1 d . . . O4 O 0.2371(6) 0.02217(17) 0.7985(3) 0.0279(8) Uani 1 1 d . . . N1 N 0.7297(5) 0.24040(18) 0.7945(2) 0.0143(7) Uani 1 1 d . . . N3 N 0.2928(5) 0.24736(18) 0.6722(2) 0.0140(7) Uani 1 1 d . . . N4 N 0.4254(6) 0.33998(18) 0.6364(2) 0.0160(7) Uani 1 1 d . . . N8 N 0.6158(6) 0.33292(18) 0.8390(2) 0.0165(7) Uani 1 1 d . . . C1 C 0.6956(6) 0.1914(2) 0.6218(3) 0.0166(8) Uani 1 1 d . . . C2 C 0.7439(7) 0.0723(2) 0.6757(3) 0.0226(10) Uani 1 1 d . . . C3 C 0.3225(6) 0.1875(2) 0.8402(3) 0.0148(8) Uani 1 1 d . . . C4 C 0.2461(7) 0.0738(2) 0.7750(3) 0.0187(9) Uani 1 1 d . . . C10 C 0.8401(7) 0.2548(2) 0.8752(3) 0.0182(9) Uani 1 1 d . . . H10 H 0.9478 0.2290 0.9066 0.022 Uiso 1 1 calc R . . C11 C 0.7713(7) 0.3116(2) 0.9030(3) 0.0186(9) Uani 1 1 d . . . H11 H 0.8211 0.3326 0.9564 0.022 Uiso 1 1 calc R . . C12 C 0.5943(6) 0.2890(2) 0.7746(3) 0.0136(8) Uani 1 1 d . . . C13 C 0.4389(6) 0.2921(2) 0.6963(3) 0.0145(8) Uani 1 1 d . . . C14 C 0.2635(7) 0.3244(2) 0.5719(3) 0.0188(9) Uani 1 1 d . . . H14 H 0.2167 0.3488 0.5209 0.023 Uiso 1 1 calc R . . C15 C 0.1829(7) 0.2679(2) 0.5944(3) 0.0177(9) Uani 1 1 d . . . H15 H 0.0680 0.2459 0.5616 0.021 Uiso 1 1 calc R . . C16 C 0.4820(8) 0.3888(2) 0.8477(3) 0.0213(9) Uani 1 1 d . . . H16A H 0.4351 0.4084 0.7901 0.026 Uiso 1 1 calc R . . H16B H 0.5635 0.4220 0.8848 0.026 Uiso 1 1 calc R . . C17 C 0.2956(8) 0.3707(3) 0.8859(4) 0.0298(12) Uani 1 1 d . . . H17A H 0.3412 0.3479 0.9414 0.036 Uiso 1 1 calc R . . H17B H 0.2067 0.3407 0.8463 0.036 Uiso 1 1 calc R . . C18 C 0.1718(10) 0.4305(3) 0.9007(5) 0.0458(18) Uani 1 1 d . . . H18A H 0.2616 0.4612 0.9376 0.069 Uiso 1 1 calc R . . H18B H 0.0566 0.4178 0.9290 0.069 Uiso 1 1 calc R . . H18C H 0.1174 0.4511 0.8452 0.069 Uiso 1 1 calc R . . C19 C 0.5715(8) 0.3936(2) 0.6320(3) 0.0219(9) Uani 1 1 d . . . H19A H 0.6634 0.3986 0.6887 0.026 Uiso 1 1 calc R . . H19B H 0.4931 0.4346 0.6190 0.026 Uiso 1 1 calc R . . C20 C 0.7022(7) 0.3817(2) 0.5633(3) 0.0223(10) Uani 1 1 d . . . H20A H 0.7903 0.3430 0.5792 0.027 Uiso 1 1 calc R . . H20B H 0.6100 0.3725 0.5076 0.027 Uiso 1 1 calc R . . C21 C 0.8387(9) 0.4393(3) 0.5524(4) 0.0336(13) Uani 1 1 d . . . H21A H 0.7520 0.4776 0.5356 0.050 Uiso 1 1 calc R . . H21B H 0.9199 0.4297 0.5075 0.050 Uiso 1 1 calc R . . H21C H 0.9325 0.4479 0.6070 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rh1 0.01138(14) 0.01316(16) 0.01707(17) 0.00012(13) 0.00272(12) 0.00064(12) Rh2 0.01107(14) 0.01304(16) 0.01490(16) 0.00032(12) 0.00270(11) -0.00079(11) Cl1 0.0235(5) 0.0217(5) 0.0231(5) 0.0082(4) 0.0052(4) 0.0040(4) Cl2 0.0228(5) 0.0201(5) 0.0185(5) -0.0030(4) 0.0053(4) -0.0036(4) O1 0.0222(16) 0.0229(17) 0.0162(16) -0.0011(13) 0.0025(13) 0.0013(13) O2 0.0268(19) 0.0213(19) 0.054(3) -0.0116(18) 0.0104(18) 0.0017(15) O3 0.0223(16) 0.0234(17) 0.0190(17) 0.0024(13) 0.0047(13) -0.0022(13) O4 0.0275(18) 0.0177(17) 0.039(2) 0.0009(15) 0.0063(16) -0.0028(14) N1 0.0117(15) 0.0179(18) 0.0130(17) 0.0006(14) 0.0012(13) -0.0009(13) N3 0.0125(15) 0.0139(17) 0.0156(17) 0.0011(14) 0.0030(13) 0.0016(13) N4 0.0188(17) 0.0136(17) 0.0165(18) 0.0019(14) 0.0054(14) 0.0007(14) N8 0.0189(17) 0.0152(18) 0.0156(18) -0.0004(14) 0.0041(14) -0.0037(14) C1 0.0118(18) 0.015(2) 0.024(2) -0.0067(17) 0.0059(16) -0.0003(15) C2 0.015(2) 0.017(2) 0.036(3) 0.001(2) 0.0063(19) 0.0025(17) C3 0.0131(18) 0.015(2) 0.016(2) 0.0040(16) 0.0022(15) 0.0001(15) C4 0.0148(19) 0.023(2) 0.018(2) 0.0003(18) 0.0031(16) 0.0016(17) C10 0.0137(19) 0.024(2) 0.016(2) -0.0005(17) 0.0022(16) -0.0034(17) C11 0.019(2) 0.023(2) 0.014(2) -0.0018(17) 0.0023(16) -0.0065(17) C12 0.0142(18) 0.0122(19) 0.0148(19) -0.0012(15) 0.0038(15) -0.0017(15) C13 0.0153(18) 0.0131(19) 0.015(2) -0.0007(16) 0.0041(15) 0.0019(15) C14 0.019(2) 0.021(2) 0.016(2) 0.0032(17) 0.0033(17) 0.0052(17) C15 0.0131(18) 0.023(2) 0.016(2) 0.0014(17) 0.0022(16) 0.0034(16) C16 0.029(2) 0.012(2) 0.025(2) -0.0008(17) 0.0111(19) -0.0023(18) C17 0.020(2) 0.019(2) 0.054(4) 0.006(2) 0.015(2) 0.0007(19) C18 0.040(3) 0.020(3) 0.087(5) 0.004(3) 0.035(4) 0.004(2) C19 0.031(2) 0.014(2) 0.023(2) -0.0011(18) 0.0111(19) -0.0038(18) C20 0.020(2) 0.020(2) 0.028(2) -0.0045(19) 0.0085(19) -0.0006(18) C21 0.040(3) 0.020(2) 0.046(3) -0.002(2) 0.024(3) -0.005(2) _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 Rh1 C1 1.848(5) . yes Rh1 C2 1.855(5) . yes Rh1 N1 2.092(4) . yes Rh1 Cl1 2.3674(12) . yes Rh1 Rh2 3.1426(5) . yes Rh1 Rh2 3.4255(5) 1_655 yes Rh2 C3 1.834(4) . yes Rh2 C4 1.851(5) . yes Rh2 N3 2.111(4) . yes Rh2 Cl2 2.3636(12) . yes O1 C1 1.126(6) . ? O2 C2 1.126(6) . ? O3 C3 1.148(6) . ? O4 C4 1.131(6) . ? N1 C12 1.339(5) . ? N1 C10 1.379(6) . ? N3 C13 1.334(6) . ? N3 C15 1.373(6) . ? N4 C13 1.357(6) . ? N4 C14 1.371(6) . ? N4 C19 1.473(6) . ? N8 C12 1.348(6) . ? N8 C11 1.372(6) . ? N8 C16 1.470(6) . ? C10 C11 1.355(7) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.454(6) . ? C14 C15 1.352(7) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.505(7) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.517(7) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.518(6) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.516(7) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 Rh1 C2 89.1(2) . . ? C1 Rh1 N1 93.43(17) . . ? C2 Rh1 N1 176.76(19) . . ? C1 Rh1 Cl1 176.94(14) . . ? C2 Rh1 Cl1 87.85(17) . . ? N1 Rh1 Cl1 89.61(11) . . ? C1 Rh1 Rh2 89.67(13) . . ? C2 Rh1 Rh2 96.49(14) . . ? N1 Rh1 Rh2 81.51(10) . . ? Cl1 Rh1 Rh2 90.41(3) . . ? C1 Rh1 Rh2 89.45(13) . 1_655 ? C2 Rh1 Rh2 85.99(14) . 1_655 ? N1 Rh1 Rh2 96.05(10) . 1_655 ? Cl1 Rh1 Rh2 90.60(3) . 1_655 ? Rh2 Rh1 Rh2 177.352(17) . 1_655 ? C3 Rh2 C4 88.5(2) . . ? C3 Rh2 N3 94.22(17) . . ? C4 Rh2 N3 176.39(17) . . ? C3 Rh2 Cl2 176.46(14) . . ? C4 Rh2 Cl2 87.98(15) . . ? N3 Rh2 Cl2 89.32(11) . . ? C3 Rh2 Rh1 88.30(13) . . ? C4 Rh2 Rh1 96.29(14) . . ? N3 Rh2 Rh1 81.42(10) . . ? Cl2 Rh2 Rh1 92.02(3) . . ? C12 N1 C10 105.7(4) . . ? C12 N1 Rh1 127.9(3) . . ? C10 N1 Rh1 125.5(3) . . ? C13 N3 C15 106.0(4) . . ? C13 N3 Rh2 127.6(3) . . ? C15 N3 Rh2 125.7(3) . . ? C13 N4 C14 106.9(4) . . ? C13 N4 C19 128.1(4) . . ? C14 N4 C19 124.3(4) . . ? C12 N8 C11 107.6(4) . . ? C12 N8 C16 127.8(4) . . ? C11 N8 C16 124.1(4) . . ? O1 C1 Rh1 178.2(4) . . ? O2 C2 Rh1 178.4(5) . . ? O3 C3 Rh2 177.5(4) . . ? O4 C4 Rh2 176.2(4) . . ? C11 C10 N1 109.5(4) . . ? C11 C10 H10 125.2 . . ? N1 C10 H10 125.2 . . ? C10 C11 N8 106.6(4) . . ? C10 C11 H11 126.7 . . ? N8 C11 H11 126.7 . . ? N1 C12 N8 110.6(4) . . ? N1 C12 C13 124.4(4) . . ? N8 C12 C13 124.9(4) . . ? N3 C13 N4 110.6(4) . . ? N3 C13 C12 124.7(4) . . ? N4 C13 C12 124.7(4) . . ? C15 C14 N4 107.1(4) . . ? C15 C14 H14 126.5 . . ? N4 C14 H14 126.5 . . ? C14 C15 N3 109.4(4) . . ? C14 C15 H15 125.3 . . ? N3 C15 H15 125.3 . . ? N8 C16 C17 112.7(4) . . ? N8 C16 H16A 109.1 . . ? C17 C16 H16A 109.1 . . ? N8 C16 H16B 109.1 . . ? C17 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C16 C17 C18 110.9(4) . . ? C16 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.0 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N4 C19 C20 111.7(4) . . ? N4 C19 H19A 109.3 . . ? C20 C19 H19A 109.3 . . ? N4 C19 H19B 109.3 . . ? C20 C19 H19B 109.3 . . ? H19A C19 H19B 107.9 . . ? C21 C20 C19 112.1(4) . . ? C21 C20 H20A 109.2 . . ? C19 C20 H20A 109.2 . . ? C21 C20 H20B 109.2 . . ? C19 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? 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 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.879 _refine_diff_density_min -1.751 _refine_diff_density_rms 0.141 #===END======================================================================== data_Pr2bim _database_code_depnum_ccdc_archive 'CCDC 872004' #TrackingRef 'Laurila.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H18 N4' _chemical_formula_sum 'C12 H18 N4' _chemical_formula_weight 218.30 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 0.0000 0.0000 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _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 13.3579(5) _cell_length_b 9.9265(4) _cell_length_c 18.7600(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.731(2) _cell_angle_gamma 90.00 _cell_volume 2382.22(16) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7893 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 30.55 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9760 _exptl_absorpt_correction_T_max 0.9841 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _publ_section_exptl_refinement ; The hydrogen atoms were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.98-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.74 \%A from atom C23 and the deepest hole is located 0.86 \%A from atom N5. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'curved graphite crystal' _diffrn_measurement_device_type 'Bruker KAPPA APEX II DUO CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22744 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5482 _reflns_number_gt 4408 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2g (Brandenburg, 2011)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0526P)^2^+0.6878P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5482 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1041 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 N1 N 0.27189(7) 1.00225(10) 0.06623(5) 0.0168(2) Uani 1 1 d . . . N2 N 0.33308(7) 0.98548(10) 0.18961(5) 0.0175(2) Uani 1 1 d . . . N3 N 0.48224(7) 0.77035(10) 0.17656(5) 0.0179(2) Uani 1 1 d . . . N4 N 0.41472(8) 0.77705(10) 0.05327(5) 0.0206(2) Uani 1 1 d . . . N5 N 0.01547(7) 0.72819(10) 0.16875(5) 0.0179(2) Uani 1 1 d . . . N6 N -0.05553(8) 0.73973(10) 0.04580(5) 0.0203(2) Uani 1 1 d . . . N7 N -0.18624(7) 0.49367(10) 0.05770(5) 0.0179(2) Uani 1 1 d . . . N8 N -0.17363(7) 0.56676(10) 0.17235(5) 0.0187(2) Uani 1 1 d . . . C1 C 0.25035(9) 0.98307(12) -0.01435(6) 0.0194(2) Uani 1 1 d . . . H1A H 0.1752 1.0003 -0.0386 0.023 Uiso 1 1 calc R . . H1B H 0.2647 0.8881 -0.0241 0.023 Uiso 1 1 calc R . . C2 C 0.31448(10) 1.07390(14) -0.04908(7) 0.0274(3) Uani 1 1 d . . . H2A H 0.3894 1.0500 -0.0296 0.033 Uiso 1 1 calc R . . H2B H 0.3060 1.1687 -0.0356 0.033 Uiso 1 1 calc R . . C3 C 0.27946(12) 1.05896(16) -0.13369(7) 0.0359(3) Uani 1 1 d . . . H3A H 0.2863 0.9646 -0.1469 0.054 Uiso 1 1 calc R . . H3B H 0.3233 1.1156 -0.1553 0.054 Uiso 1 1 calc R . . H3C H 0.2063 1.0871 -0.1531 0.054 Uiso 1 1 calc R . . C4 C 0.22036(9) 1.09671(11) 0.09609(6) 0.0184(2) Uani 1 1 d . . . H4 H 0.1685 1.1581 0.0695 0.022 Uiso 1 1 calc R . . C5 C 0.25832(9) 1.08491(11) 0.17124(6) 0.0183(2) Uani 1 1 d . . . H5 H 0.2363 1.1379 0.2062 0.022 Uiso 1 1 calc R . . C6 C 0.34008(8) 0.93750(11) 0.12497(6) 0.0162(2) Uani 1 1 d . . . C7 C 0.41075(8) 0.82979(11) 0.11745(6) 0.0164(2) Uani 1 1 d . . . C8 C 0.53239(9) 0.67356(12) 0.14737(7) 0.0211(2) Uani 1 1 d . . . H8 H 0.5855 0.6140 0.1743 0.025 Uiso 1 1 calc R . . C9 C 0.49101(9) 0.67961(12) 0.07226(7) 0.0217(3) Uani 1 1 d . . . H9 H 0.5118 0.6243 0.0377 0.026 Uiso 1 1 calc R . . C10 C 0.50816(9) 0.79831(12) 0.25669(6) 0.0193(2) Uani 1 1 d . . . H10A H 0.4954 0.8949 0.2640 0.023 Uiso 1 1 calc R . . H10B H 0.5835 0.7806 0.2798 0.023 Uiso 1 1 calc R . . C11 C 0.44522(9) 0.71420(12) 0.29602(7) 0.0218(3) Uani 1 1 d . . . H11A H 0.4536 0.6174 0.2863 0.026 Uiso 1 1 calc R . . H11B H 0.3702 0.7373 0.2766 0.026 Uiso 1 1 calc R . . C12 C 0.48284(10) 0.74114(14) 0.37967(7) 0.0277(3) Uani 1 1 d . . . H12A H 0.5564 0.7150 0.3991 0.041 Uiso 1 1 calc R . . H12B H 0.4408 0.6885 0.4046 0.041 Uiso 1 1 calc R . . H12C H 0.4755 0.8373 0.3890 0.041 Uiso 1 1 calc R . . C13 C 0.03949(9) 0.68696(11) 0.24684(6) 0.0192(2) Uani 1 1 d . . . H13A H 0.1162 0.6881 0.2693 0.023 Uiso 1 1 calc R . . H13B H 0.0152 0.5933 0.2491 0.023 Uiso 1 1 calc R . . C14 C -0.01084(9) 0.77694(12) 0.29220(6) 0.0205(2) Uani 1 1 d . . . H14A H -0.0875 0.7779 0.2694 0.025 Uiso 1 1 calc R . . H14B H 0.0152 0.8702 0.2919 0.025 Uiso 1 1 calc R . . C15 C 0.01411(10) 0.72682(13) 0.37208(7) 0.0241(3) Uani 1 1 d . . . H15A H -0.0123 0.6348 0.3724 0.036 Uiso 1 1 calc R . . H15B H -0.0193 0.7858 0.4004 0.036 Uiso 1 1 calc R . . H15C H 0.0900 0.7276 0.3949 0.036 Uiso 1 1 calc R . . C16 C 0.07006(9) 0.82426(12) 0.14261(7) 0.0219(3) Uani 1 1 d . . . H16 H 0.1271 0.8766 0.1712 0.026 Uiso 1 1 calc R . . C17 C 0.02610(9) 0.82948(12) 0.06768(7) 0.0221(3) Uani 1 1 d . . . H17 H 0.0486 0.8872 0.0349 0.027 Uiso 1 1 calc R . . C18 C -0.06023(8) 0.68045(11) 0.10829(6) 0.0167(2) Uani 1 1 d . . . C19 C -0.13831(8) 0.58113(11) 0.11354(6) 0.0168(2) Uani 1 1 d . . . C20 C -0.25603(9) 0.42019(12) 0.08323(6) 0.0195(2) Uani 1 1 d . . . H20 H -0.3015 0.3514 0.0572 0.023 Uiso 1 1 calc R . . C21 C -0.24692(9) 0.46561(12) 0.15321(6) 0.0192(2) Uani 1 1 d . . . H21 H -0.2858 0.4321 0.1846 0.023 Uiso 1 1 calc R . . C22 C -0.16600(9) 0.47068(12) -0.01422(6) 0.0206(2) Uani 1 1 d . . . H22A H -0.1594 0.3726 -0.0214 0.025 Uiso 1 1 calc R . . H22B H -0.0986 0.5133 -0.0134 0.025 Uiso 1 1 calc R . . C23 C -0.25138(9) 0.52657(12) -0.07948(6) 0.0215(3) Uani 1 1 d . . . H23A H -0.2571 0.6251 -0.0735 0.026 Uiso 1 1 calc R . . H23B H -0.3192 0.4853 -0.0804 0.026 Uiso 1 1 calc R . . C24 C -0.22743(10) 0.49733(15) -0.15266(7) 0.0294(3) Uani 1 1 d . . . H24A H -0.1592 0.5355 -0.1511 0.044 Uiso 1 1 calc R . . H24B H -0.2815 0.5380 -0.1938 0.044 Uiso 1 1 calc R . . H24C H -0.2262 0.3997 -0.1601 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0180(4) 0.0159(4) 0.0151(5) 0.0007(4) 0.0025(4) -0.0003(4) N2 0.0180(4) 0.0180(5) 0.0162(5) 0.0005(4) 0.0043(4) 0.0005(4) N3 0.0189(5) 0.0183(5) 0.0156(5) 0.0007(4) 0.0037(4) 0.0021(4) N4 0.0240(5) 0.0201(5) 0.0173(5) -0.0009(4) 0.0054(4) 0.0014(4) N5 0.0193(5) 0.0160(5) 0.0174(5) 0.0005(4) 0.0033(4) -0.0002(4) N6 0.0213(5) 0.0209(5) 0.0189(5) 0.0030(4) 0.0060(4) 0.0017(4) N7 0.0178(4) 0.0183(5) 0.0170(5) -0.0024(4) 0.0041(4) 0.0007(4) N8 0.0199(5) 0.0185(5) 0.0173(5) -0.0006(4) 0.0047(4) 0.0000(4) C1 0.0213(5) 0.0201(6) 0.0138(5) -0.0001(4) 0.0003(4) 0.0002(4) C2 0.0327(7) 0.0312(7) 0.0184(6) -0.0026(5) 0.0076(5) -0.0094(6) C3 0.0481(9) 0.0406(8) 0.0193(7) -0.0008(6) 0.0104(6) -0.0120(7) C4 0.0170(5) 0.0161(5) 0.0214(6) 0.0010(4) 0.0045(4) 0.0000(4) C5 0.0187(5) 0.0170(5) 0.0196(6) 0.0002(4) 0.0060(4) -0.0003(4) C6 0.0165(5) 0.0161(5) 0.0149(5) 0.0010(4) 0.0028(4) -0.0024(4) C7 0.0171(5) 0.0164(5) 0.0148(5) 0.0010(4) 0.0031(4) -0.0016(4) C8 0.0217(6) 0.0200(6) 0.0216(6) 0.0000(5) 0.0061(5) 0.0036(5) C9 0.0248(6) 0.0203(6) 0.0206(6) -0.0016(5) 0.0076(5) 0.0023(5) C10 0.0199(5) 0.0210(6) 0.0145(5) -0.0001(4) 0.0008(4) 0.0020(4) C11 0.0252(6) 0.0211(6) 0.0190(6) 0.0008(5) 0.0060(5) 0.0027(5) C12 0.0323(7) 0.0330(7) 0.0174(6) 0.0032(5) 0.0068(5) 0.0043(6) C13 0.0212(5) 0.0178(5) 0.0155(5) 0.0014(4) 0.0005(4) -0.0005(4) C14 0.0244(6) 0.0168(5) 0.0183(6) -0.0007(4) 0.0032(5) -0.0015(5) C15 0.0262(6) 0.0251(6) 0.0199(6) -0.0002(5) 0.0046(5) -0.0041(5) C16 0.0211(6) 0.0192(6) 0.0249(6) 0.0013(5) 0.0057(5) -0.0030(5) C17 0.0232(6) 0.0202(6) 0.0239(6) 0.0037(5) 0.0081(5) -0.0002(5) C18 0.0175(5) 0.0162(5) 0.0155(5) -0.0001(4) 0.0032(4) 0.0031(4) C19 0.0168(5) 0.0164(5) 0.0157(5) -0.0007(4) 0.0022(4) 0.0025(4) C20 0.0174(5) 0.0175(5) 0.0227(6) -0.0019(4) 0.0041(4) -0.0002(4) C21 0.0184(5) 0.0184(6) 0.0211(6) 0.0002(4) 0.0063(4) -0.0004(4) C22 0.0217(6) 0.0239(6) 0.0163(6) -0.0043(5) 0.0055(4) 0.0023(5) C23 0.0232(6) 0.0209(6) 0.0195(6) 0.0014(5) 0.0048(5) 0.0003(5) C24 0.0319(7) 0.0360(7) 0.0188(6) -0.0013(5) 0.0047(5) 0.0008(6) _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 N1 C6 1.3709(14) . ? N1 C4 1.3743(15) . ? N1 C1 1.4676(14) . yes N2 C6 1.3308(14) . ? N2 C5 1.3755(14) . ? N3 C7 1.3711(14) . ? N3 C8 1.3723(15) . ? N3 C10 1.4687(14) . yes N4 C7 1.3279(14) . ? N4 C9 1.3755(15) . ? N5 C18 1.3686(14) . ? N5 C16 1.3739(15) . ? N5 C13 1.4648(14) . yes N6 C18 1.3293(15) . ? N6 C17 1.3761(15) . ? N7 C19 1.3692(14) . ? N7 C20 1.3737(15) . ? N7 C22 1.4684(14) . yes N8 C19 1.3266(14) . ? N8 C21 1.3759(15) . ? C1 C2 1.5141(17) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.5273(17) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.3591(16) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.4597(16) . ? C8 C9 1.3586(17) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.5183(16) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5272(16) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.5178(16) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5221(16) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.3594(17) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.4590(16) . ? C20 C21 1.3600(16) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.5176(16) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.5245(17) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 C6 N1 C4 106.69(9) . . ? C6 N1 C1 130.92(10) . . ? C4 N1 C1 122.39(9) . . ? C6 N2 C5 105.37(9) . . ? C7 N3 C8 106.55(9) . . ? C7 N3 C10 130.58(10) . . ? C8 N3 C10 122.85(10) . . ? C7 N4 C9 105.21(10) . . ? C18 N5 C16 106.62(9) . . ? C18 N5 C13 128.97(10) . . ? C16 N5 C13 124.40(10) . . ? C18 N6 C17 104.95(10) . . ? C19 N7 C20 106.54(9) . . ? C19 N7 C22 129.22(10) . . ? C20 N7 C22 124.11(10) . . ? C19 N8 C21 104.96(9) . . ? N1 C1 C2 113.49(9) . . ? N1 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? N1 C1 H1B 108.9 . . ? C2 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C1 C2 C3 110.33(10) . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 N1 106.43(10) . . ? C5 C4 H4 126.8 . . ? N1 C4 H4 126.8 . . ? C4 C5 N2 110.42(10) . . ? C4 C5 H5 124.8 . . ? N2 C5 H5 124.8 . . ? N2 C6 N1 111.09(10) . . ? N2 C6 C7 124.56(10) . . ? N1 C6 C7 124.35(10) . . ? N4 C7 N3 111.31(10) . . ? N4 C7 C6 124.90(10) . . ? N3 C7 C6 123.79(10) . . ? C9 C8 N3 106.46(10) . . ? C9 C8 H8 126.8 . . ? N3 C8 H8 126.8 . . ? C8 C9 N4 110.47(10) . . ? C8 C9 H9 124.8 . . ? N4 C9 H9 124.8 . . ? N3 C10 C11 113.15(9) . . ? N3 C10 H10A 108.9 . . ? C11 C10 H10A 108.9 . . ? N3 C10 H10B 108.9 . . ? C11 C10 H10B 108.9 . . ? H10A C10 H10B 107.8 . . ? C10 C11 C12 109.79(10) . . ? C10 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? C10 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N5 C13 C14 113.05(9) . . ? N5 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? N5 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C13 C14 C15 110.67(10) . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 N5 106.25(10) . . ? C17 C16 H16 126.9 . . ? N5 C16 H16 126.9 . . ? C16 C17 N6 110.68(10) . . ? C16 C17 H17 124.7 . . ? N6 C17 H17 124.7 . . ? N6 C18 N5 111.49(10) . . ? N6 C18 C19 125.09(10) . . ? N5 C18 C19 123.37(10) . . ? N8 C19 N7 111.60(10) . . ? N8 C19 C18 124.13(10) . . ? N7 C19 C18 124.25(10) . . ? C21 C20 N7 106.22(10) . . ? C21 C20 H20 126.9 . . ? N7 C20 H20 126.9 . . ? C20 C21 N8 110.67(10) . . ? C20 C21 H21 124.7 . . ? N8 C21 H21 124.7 . . ? N7 C22 C23 112.96(9) . . ? N7 C22 H22A 109.0 . . ? C23 C22 H22A 109.0 . . ? N7 C22 H22B 109.0 . . ? C23 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C22 C23 C24 110.67(10) . . ? C22 C23 H23A 109.5 . . ? C24 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.276 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.041 #===END========================================================================